# Kal Penn

An episode of [Drama Queens](https://invisiblenetwork.ai/podcast/1571792783), 14 Oct 2026, 54 min.

Audio: https://podtrac.com/pts/redirect.mp3/pscrb.fm/rss/p/traffic.omny.fm/d/clips/e73c998e-6e60-432f-8610-ae210140c5b1/e53aefd3-699f-4685-9a84-aed700f383fa/63cdf60f-b38a-4271-87f8-b4e30073e523/audio.mp3?utm_source=Podcast&in_playlist=cf2e6477-1a1d-4442-8b33-ae320005bb63

From Hollywood to the White House and back again, Kal Penn has had a front row seat to fame, power, politics and the systems behind them. Kal reveals the wild ride of Harold & Kumar, his decision to put acting on hold for the Obama White House, and what he’s learned about public life along the way. Plus, the twisted real-life saga behind his new movie, "Trust Me, I’m a Doctor." See omnystudio.com/listener for privacy information.

## Transcript

[0:00] Speaker 1: Hi, everyone. It's Sophia. Welcome to Work in Progress. Welcome
[0:15] Speaker 1: back to Work in Progress, friends. This week, we sure
[0:18] Speaker 1: have a Whipsmartie for you. Today's guest has built a
[0:22] Speaker 1: career that refuses to fit in one lane, which is
[0:25] Speaker 1: something I absolutely love about him. From Hollywood to the
[0:29] Speaker 1: White House, as an actor, a writer, a comedian, and
[0:32] Speaker 1: someone who does great political commentary, have you guessed yet?
[0:36] Speaker 1: Today's guest is Cal Penn. We actually overlapped on one
[0:40] Speaker 1: of my first jobs ever, Van Wilder, back in the
[0:44] Speaker 1: early 2000s. He went on to make Harold and Kumar
[0:48] Speaker 1: a cult classic hit that then had two more sequels.
[0:52] Speaker 1: He took a break from Hollywood to work in the
[0:54] Speaker 1: Obama White House on youth outreach and a whole bunch
[0:57] Speaker 1: of other interesting stuff you'll hear about today. In 2021,
[1:01] Speaker 1: he published his first memoir, You Can't Be Serious, which
[1:04] Speaker 1: pulls all of his worlds together and reveals so many
[1:07] Speaker 1: improbable stories, Hollywood frustrations, and takes some real unexpected turns
[1:12] Speaker 1: behind a life that has taken some pretty wild detours.
[1:16] Speaker 1: The thing I really appreciate about Cal is he's also
[1:19] Speaker 1: a deep nerd. He loves to read. He loves to research.
[1:22] Speaker 1: He loves to understand systems. And he has such a
[1:25] Speaker 1: fascinating perspective on identity and ambition and public life that
[1:31] Speaker 1: really makes him a person I like to look to
[1:34] Speaker 1: for thoughts, opinions, and dialogue. His latest endeavor is a
[1:39] Speaker 1: film called Trust Me, I'm a Doctor. And in this movie,
[1:43] Speaker 1: he plays a real person, Dr. Sandeep Kapoor, who treated
[1:46] Speaker 1: Anna Nicole Smith and whose life was absolutely upended after
[1:50] Speaker 1: she died. Not only is it an interesting story, but
[1:53] Speaker 1: it takes place at the height of of the early
[1:57] Speaker 1: 2000s tabloid era and really explores how fame and media
[2:01] Speaker 1: scrutiny and the justice system can completely reshape a person's life.
[2:05] Speaker 1: And after everything Cal's seen from the backlots of Hollywood
[2:10] Speaker 1: to the Oval Office in DC and back again, I
[2:13] Speaker 1: really wanna find out what all these experiences have taught
[2:16] Speaker 1: him about fame, power, politics, and himself. Let's dive in
[2:21] Speaker 1: with Cal Penn.
[2:24] Speaker 2: Hello.
[2:24] Speaker 1: Hi, how are you?
[2:26] Speaker 2: Good, how are you? I'm good.
[2:28] Speaker 1: It's so nice to see you.
[2:29] Speaker 2: Good to see you.
[2:30] Speaker 1: Well, this is so fun and congrats on the movie.
[2:33] Speaker 1: I mean, gosh, it's wild.
[2:36] Speaker 2: Thank you. It's a weird story. It's a crazy story.
[2:38] Speaker 1: It is, but I just, oh, it's great. Okay, we're
[2:41] Speaker 1: going to get into that. But before we get into
[2:43] Speaker 1: the present and work and all the things, I actually
[2:47] Speaker 1: want to go back to the place that we have
[2:50] Speaker 1: in common.
[2:51] Speaker 2: Yeah.
[2:51] Speaker 1: Take us back to 1980s New Jersey. What was your
[2:55] Speaker 1: childhood like? If we could bump into Cal at eight
[3:00] Speaker 1: or nine years old, do you think you would see
[3:03] Speaker 1: yourself in that little boy?
[3:04] Speaker 2: Oh, interesting. I've never thought about it that way, like
[3:08] Speaker 2: how far we've changed looking backwards. Yeah, I'm sure there
[3:12] Speaker 2: were some things in there. I mean, you're asking 1980s
[3:17] Speaker 2: elementary school New Jersey to you. I was talking to
[3:20] Speaker 2: some friends over the weekend and realized that I think
[3:24] Speaker 2: our music teacher in elementary school was a giant stoner
[3:28] Speaker 2: and may have been high while teaching, which was fine.
[3:32] Speaker 2: She was teaching music and we obviously didn't know she
[3:34] Speaker 2: was lovely. Um, but so I look back and think
[3:37] Speaker 2: of all those things. I was like, I wonder how
[3:39] Speaker 2: much stuff there was that I just didn't know and
[3:41] Speaker 2: didn't register. Um, but I loved growing up in New Jersey.
[3:44] Speaker 2: I think, you know, a lot of the, you're right
[3:47] Speaker 2: outside New York city. Um, I'm sure plenty of people
[3:51] Speaker 2: watching and listening will roll their eyes at New Jersey,
[3:54] Speaker 2: but you are wrong. And here's what I mean. Like, okay,
[3:57] Speaker 2: you mentioned being eight or nine years old, right? You
[3:59] Speaker 2: take a school trip to, you're learning about dinosaurs in class.
[4:03] Speaker 2: You take a school trip to the Museum of Natural
[4:05] Speaker 2: History in Manhattan and see all the dinosaurs. Yes. And
[4:09] Speaker 2: I remember thinking, obviously this is very cool, but like
[4:13] Speaker 2: as the years went on, it wasn't until college. I
[4:16] Speaker 2: went to school at UCLA, so I went out west.
[4:19] Speaker 2: And that was the first time I realized that when
[4:21] Speaker 2: other kids learned about dinosaurs, they didn't have the chance
[4:24] Speaker 2: to go on a field trip to actually look at
[4:26] Speaker 2: dinosaur bones at a world-class museum. And so taking all
[4:30] Speaker 2: of that for granted, I was thinking about like, okay, yeah,
[4:33] Speaker 2: there was that. There was a lot of children's theater
[4:36] Speaker 2: that you could see all over New Jersey or in
[4:38] Speaker 2: the city. When we learned about the UN in sixth grade,
[4:41] Speaker 2: we just went to the UN to do a tour.
[4:43] Speaker 2: This is a public school, by the way. I didn't
[4:45] Speaker 2: go to a private school or anything. Totally. So I
[4:48] Speaker 2: don't know. I guess when I think back to those days,
[4:52] Speaker 2: a lot of that stuff pops up.
[4:53] Speaker 1: Yeah. When you were a little boy, did you know
[4:57] Speaker 1: you wanted to be a performer?
[4:58] Speaker 2: A little bit later. I think up until sixth grade,
[5:05] Speaker 2: I wanted to be an astronaut, which is why you
[5:07] Speaker 2: see the space shuttle behind me. And I went to
[5:11] Speaker 2: space camp as a kid. I did too! Did you really? Yes!
[5:15] Speaker 2: Huntsville or Florida? Yeah.
[5:17] Speaker 1: I went in, there's one in Idyllwild in California, or
[5:19] Speaker 1: at least there was when I was little.
[5:21] Speaker 2: Very cool, yeah.
[5:23] Speaker 1: And I just loved it. I have like such a
[5:26] Speaker 1: deeply emotional, I don't even want to say relationship, just
[5:31] Speaker 1: like I'm so emotionally tied to space and the history
[5:35] Speaker 1: of all things NASA. Makes me cry.
[5:37] Speaker 2: Yeah, we are on the same boat. It was when
[5:42] Speaker 2: I found out that in those days, at least, you
[5:44] Speaker 2: had to have perfect vision to be a shuttle commander.
[5:48] Speaker 2: The sixth grade me was like, well, that's definitely not
[5:51] Speaker 2: going to happen.
[5:51] Speaker 1: That's out.
[5:53] Speaker 2: I didn't know about LASIK or anything like that. And
[5:55] Speaker 2: I was like, well, now I obviously can't be an astronaut,
[5:58] Speaker 2: so I'll just try to play one. Wow, I love that.
[6:03] Speaker 1: How did that go over when you told your parents that?
[6:06] Speaker 2: Oh, that I wanted to be an actor? Yeah. I mean,
[6:08] Speaker 2: it didn't go over well, I would imagine, like a
[6:10] Speaker 2: lot of people. Yeah. Are your parents artists or actors?
[6:16] Speaker 1: My dad is a photographer. Okay. So a type of artist.
[6:20] Speaker 1: But my parents were like, absolutely, that's not a thing
[6:23] Speaker 1: that you're going to be.
[6:24] Speaker 2: No.
[6:25] Speaker 1: You know, very like my mom's family all came to
[6:28] Speaker 1: New York and New Jersey from Italy. It was very
[6:31] Speaker 1: much the like immigrant energy of like, you could be
[6:34] Speaker 1: a doctor or a lawyer or a lawyer.
[6:36] Speaker 2: Or a doctor. Yeah.
[6:37] Speaker 1: And I was like, okay, but I think I want
[6:40] Speaker 1: to be an actor.
[6:41] Speaker 2: Totally. Yeah.
[6:42] Speaker 1: It wasn't great.
[6:43] Speaker 2: We share that in common then because my parents are immigrants.
[6:47] Speaker 2: You know, when they moved to the U.S., it was
[6:49] Speaker 2: this what they call the post-1965 wave of Asian immigration,
[6:55] Speaker 2: where there was a particular immigration law that changed that
[6:58] Speaker 2: allowed people from certain Asian countries to come, but only
[7:02] Speaker 2: if they had either already had a graduate degree in
[7:07] Speaker 2: certain fields or were pursuing one. So in the case
[7:09] Speaker 2: of my parents, my dad got into an engineering graduate
[7:12] Speaker 2: program in New Jersey, and that's why he got his
[7:15] Speaker 2: visa to come here. Wow. he and my mom got
[7:18] Speaker 2: married in India, but she had a master's in chemistry.
[7:21] Speaker 2: So it was like, we didn't have enough engineers or
[7:23] Speaker 2: doctors or things like, which is why you see that
[7:25] Speaker 2: like old school generation of a lot of Brown doctors
[7:28] Speaker 2: and engineers. There's nothing genetically inherent about it. It's just
[7:32] Speaker 2: the immigration law and what they were screening for. But
[7:35] Speaker 2: so because of that, all of their friends and the
[7:36] Speaker 2: whole kind of community was very, very much like, no,
[7:40] Speaker 2: you're either to your point, a doctor or an engineer
[7:43] Speaker 2: or things that we know that gave us a better life.
[7:46] Speaker 2: I talked to my parents about this at length when
[7:49] Speaker 2: I wrote a book almost four years ago now. And
[7:53] Speaker 2: it's a memoir and it's meant to just kind of
[7:54] Speaker 2: be funny and light. And I love like Tina Fey's
[7:57] Speaker 2: books and Rainn Wilson and Mindy Kaling. And so I
[8:01] Speaker 2: wanted it to be very similar in tone, but then
[8:03] Speaker 2: the subtext is obviously stuff that's a little more serious.
[8:06] Speaker 2: And I remember I called my parents when I was
[8:09] Speaker 2: turning in my final draft. I was like, hey, I'm
[8:10] Speaker 2: looking for a number that I can put in the
[8:14] Speaker 2: book that that describes how embarrassed you were when I
[8:19] Speaker 2: would tell the family friends and the aunties and uncles
[8:21] Speaker 2: that like, you know, when I was 15 and cocky
[8:25] Speaker 2: that I was going to be a filmmaker instead of
[8:27] Speaker 2: a doctor or be an actor instead of an engineer.
[8:30] Speaker 2: And they both, this was over, over zoom. They were
[8:32] Speaker 2: both like embarrassed. No, we were never embarrassed. We just,
[8:38] Speaker 2: we didn't think that this was a career that anybody
[8:40] Speaker 2: could have, especially somebody who, was from our community. And
[8:44] Speaker 2: so we were scared, we weren't embarrassed. And I was like,
[8:47] Speaker 2: you know, why do I have to be in my
[8:50] Speaker 2: late thirties or early forties before I actually asked my
[8:53] Speaker 2: parents this and actually understand that they were scared, not embarrassed.
[8:57] Speaker 2: Like I'm carrying that around for this long, you know? So, um,
[9:01] Speaker 2: so when I think back on it, I laugh a
[9:02] Speaker 2: lot because it makes sense. I don't have kids. So
[9:06] Speaker 2: the things that they've explained to me, I can understand that.
[9:09] Speaker 2: I can feel as far as having nieces and nephews
[9:11] Speaker 2: and being the fun uncle to a lot of my friends' kids.
[9:14] Speaker 2: But man, I can't understand how that must have really
[9:17] Speaker 2: been deeply scary to be like, okay, you're going to
[9:21] Speaker 2: do what? How? And then explaining to my parents that
[9:27] Speaker 2: there is a happiness quotient that doesn't come from financial stability.
[9:32] Speaker 2: And I don't know if you feel like this, Sophia,
[9:35] Speaker 2: but I feel like whenever we get asked these questions...
[9:39] Speaker 2: I acknowledge like what a place of privilege I am
[9:41] Speaker 2: in today to be able to say, you know, go
[9:45] Speaker 2: follow your dreams, et cetera, et cetera. But I remember
[9:48] Speaker 2: way back in the day, like in college, working a
[9:52] Speaker 2: bunch of odd jobs for those like eight years. It
[9:55] Speaker 2: was all like my goal was can I pay my
[9:58] Speaker 2: rent through my art period? Can I just, is there
[10:01] Speaker 2: a month where the rent and groceries and gas for
[10:05] Speaker 2: auditions will be covered by like a commercial or a
[10:12] Speaker 2: couple of days on a TV show that I might
[10:14] Speaker 2: be lucky enough to get?
[10:15] Speaker 1: Obviously our stories are different, but I really related to
[10:18] Speaker 1: this on multiple levels, but you talk about your book.
[10:22] Speaker 1: And for our friends at home, if you've been living
[10:24] Speaker 1: under a rock and you haven't read the book I'm
[10:26] Speaker 1: referring to, Cal's 2021 memoir called You Can't Be Serious.
[10:31] Speaker 1: Perfect title, by the way.
[10:32] Speaker 2: Thank you. I also narrate the audio book for those
[10:34] Speaker 2: who prefer that.
[10:35] Speaker 1: You sure do. And they can hear what a wonderful
[10:37] Speaker 1: voice you have.
[10:38] Speaker 2: Thank you.
[10:39] Speaker 1: We both have voices for podcasts.
[10:41] Speaker 2: Yes.
[10:41] Speaker 1: But you write in the book really candidly about you know,
[10:47] Speaker 1: the isms you experienced in Hollywood and the racism. And
[10:51] Speaker 1: it tracks for me and what you're saying about your parents,
[10:54] Speaker 1: where their fear probably came from. You know, you say
[10:58] Speaker 1: they didn't know a lot of people, maybe anyone from
[11:00] Speaker 1: your community who pursued this kind of a career. And
[11:03] Speaker 1: then you talk about how you almost lost The role
[11:07] Speaker 1: in Van Wilder, which was also crazy because I was like.
[11:10] Speaker 2: We were both in that movie! Totally, yes. Like, what
[11:12] Speaker 2: the hell, man?
[11:13] Speaker 1: How we have not been hanging out for the last
[11:15] Speaker 1: 20 years is so new to me. Except for at, like,
[11:18] Speaker 1: cool political things, because we're fun like that.
[11:20] Speaker 2: Exactly.
[11:22] Speaker 1: How did that early experience, like, do you think that
[11:27] Speaker 1: that changed... how you related to your career or what
[11:31] Speaker 1: was possible, or do you think it made you want
[11:33] Speaker 1: to double down and, and prove that you could continue
[11:37] Speaker 1: to do this?
[11:38] Speaker 2: I think it was probably both. And that's a, it's
[11:41] Speaker 2: a great question. Um, I hadn't thought about it in,
[11:45] Speaker 2: in that context. Like, I think when I, when I
[11:49] Speaker 2: decided to pursue theater, I should, I should say that my,
[11:51] Speaker 2: you know, I, this public high school that I went to, um,
[11:56] Speaker 2: also had a magnet program for the performing arts, which
[11:59] Speaker 2: is kind of unheard of in public education anymore in
[12:02] Speaker 2: the States. There are only a handful of publicly funded
[12:05] Speaker 2: arts high schools or arts programs in high schools. And
[12:07] Speaker 2: ours had one, and I auditioned and got in. And
[12:10] Speaker 2: without that, I would not have had the confidence to
[12:11] Speaker 2: pursue this professionally. And I'd go on auditions, and a
[12:15] Speaker 2: lot of times, I want to be clear, by the way,
[12:17] Speaker 2: if you're not watching the video of this, I am
[12:19] Speaker 2: laughing about this, which to me is important to do. Yes.
[12:22] Speaker 2: It sounds kind of shocking by 2026 standards, especially when
[12:25] Speaker 2: you realize this was not that long ago.
[12:28] Speaker 1: But the early aughts were so toxic.
[12:30] Speaker 2: They were. They were so fucking toxic. They were, yes. Yes.
[12:35] Speaker 2: So it was not uncommon if you looked like me
[12:38] Speaker 2: to walk into an audition and know that you were
[12:41] Speaker 2: reading for a part that generally was like some kind
[12:45] Speaker 2: of brown, right? Like either, so like, let's just take
[12:49] Speaker 2: Van Wilder, for instance, I was, you know, I was
[12:52] Speaker 2: reading for the part of an Indian exchange student and
[12:54] Speaker 2: my agent at the time, wonderful woman named Barbara Cameron,
[12:57] Speaker 2: who was incidentally Kirk and Candace Cameron's mom.
[12:59] Speaker 1: Oh my God.
[13:01] Speaker 2: I know crazy. The only agent, by the way, who would,
[13:04] Speaker 2: who had responded to years and years of me mailing
[13:08] Speaker 2: out headshots and resumes and trying to get somebody to
[13:10] Speaker 2: represent me. And she was the only one who called
[13:13] Speaker 2: and she's like, come audition for me. And then that's
[13:15] Speaker 2: how we started working together. But she called and was,
[13:19] Speaker 2: Her assistant called and was like, there's a great audition
[13:21] Speaker 2: for you. It's this movie called Van Wilder. Come to
[13:24] Speaker 2: the office so we can talk about it. I was like,
[13:27] Speaker 2: come to the office. This is a big deal. Well,
[13:29] Speaker 2: how about you send me the script? We had like
[13:32] Speaker 2: nascent email in those days. Send me the script and
[13:35] Speaker 2: I'll read it. Tell me the name of the character
[13:37] Speaker 2: and then I'll come into the office and we can
[13:38] Speaker 2: talk about it. I'm thinking she's like helping me prep
[13:41] Speaker 2: for the audition. And she keeps saying, just honey, just
[13:43] Speaker 2: come to the office now. Just come now. It's such
[13:46] Speaker 2: a big supporting role. It'd be amazing. There's this guy,
[13:48] Speaker 2: Ryan Reynolds. He's on the sitcom, Two Guys, A Girl,
[13:51] Speaker 2: and A Pizza Place. And everybody knew Tara Reid because
[13:54] Speaker 2: American Pie had just come out. And I finally was like,
[13:57] Speaker 2: something feels off if you need me to drive to
[13:59] Speaker 2: the office. Just send me the script. I agreed. She
[14:02] Speaker 2: agreed to send me the script. I said, what's the
[14:03] Speaker 2: name of the character? She was like, okay, you're reading
[14:06] Speaker 2: for a character named Taj Mahal. And I hung up
[14:12] Speaker 2: on her. And she called back. She's like, I had
[14:14] Speaker 2: a feeling you were going to hang up. And I
[14:16] Speaker 2: was like, yeah, look. I didn't graduate from the UCLA
[14:20] Speaker 2: School of Theater, Film, and Television to play a character
[14:23] Speaker 2: named after a building. He's named. He doesn't even have
[14:26] Speaker 2: a human name.
[14:27] Speaker 1: It's crazy.
[14:29] Speaker 2: And she was like, listen, read it and let's talk
[14:33] Speaker 2: because I think one of the things you'll find is, yes,
[14:36] Speaker 2: you are worried about all the stereotypes that are in
[14:38] Speaker 2: your head, Cal. They probably exist in this script. Mm-hmm.
[14:41] Speaker 2: but also if this character was removed from the story,
[14:45] Speaker 2: the plot wouldn't advance from start to finish. And one
[14:48] Speaker 2: of my big, one of the big challenges with stereotypes,
[14:51] Speaker 2: I think for regardless, whether it's, it's any community really that,
[14:55] Speaker 2: that has sort of dealt with them over the years
[14:58] Speaker 2: is that often they, they seem to exist when writers
[15:03] Speaker 2: are lazy. And so the butt of those types of jokes,
[15:08] Speaker 2: if they were removed, nothing would really change in terms
[15:11] Speaker 2: of the plot, right. Of these, of these projects. But
[15:15] Speaker 2: there's the rarity where like multiple things are true. Like
[15:18] Speaker 2: this could be a stereotype, but also it advances the
[15:21] Speaker 2: plot of the film. And I read it and I
[15:23] Speaker 2: called him, called a bunch of people, called some mentors
[15:26] Speaker 2: of mine. He's like, what do you think I should do?
[15:27] Speaker 2: Should I audition for this? And they all were like,
[15:30] Speaker 2: you really, you should, because having a supporting lead really,
[15:34] Speaker 2: In a studio, comedy on your resume would really make
[15:36] Speaker 2: a big difference. Your agent can pitch you for more things.
[15:39] Speaker 2: So I decided to audition. And I remember the final callback.
[15:44] Speaker 2: And for people who don't know the story, it's like, yeah,
[15:46] Speaker 2: he had like a stereotypical accent and the character had
[15:48] Speaker 2: moved from India to go to college in America just
[15:51] Speaker 2: because he wanted to get laid. Now, let's just acknowledge
[15:54] Speaker 2: that this was every movie in.
[15:57] Speaker 1: The early 2000s that's all they were about.
[16:00] Speaker 2: I am not lamenting that one way or the other
[16:02] Speaker 2: i'll also acknowledge because people ask me this all the
[16:04] Speaker 2: time and you're right um yes there was clearly a
[16:09] Speaker 2: more than fair amount of misogyny in these movies like
[16:12] Speaker 2: this is all i'm not by telling my slice of
[16:14] Speaker 2: life story i'm not trying to ignore all of the
[16:16] Speaker 2: other things that people may find challenging about these movies.
[16:19] Speaker 1: Yeah and to be clear hindsight is 2020. Like none
[16:23] Speaker 1: of this was atypical at the time.
[16:25] Speaker 2: No, exactly.
[16:26] Speaker 1: Which speaks to culture at the time. And now we
[16:29] Speaker 1: all go, yeah, one of our first movies was, I mean,
[16:33] Speaker 1: we were funny and also, ooh.
[16:37] Speaker 2: Dude, people ask me this all the time. I do
[16:41] Speaker 2: college lectures every now and then. And inevitably there will
[16:45] Speaker 2: be some very well-meaning– student who was born in 2007
[16:50] Speaker 2: or whatever, who will say, so how much do you
[16:54] Speaker 2: regret doing that movie Van Wilder? How embarrassing. How much
[16:59] Speaker 2: do you regret it? And I'm just like, first of all,
[17:02] Speaker 2: you're fucking welcome. You're welcome. Okay. I have a career
[17:06] Speaker 2: because of that. So A, you're welcome. B, if you're
[17:10] Speaker 2: actually asking me in a 2026 lens, do I wish
[17:12] Speaker 2: that one of my first movies instead Was me jumping
[17:15] Speaker 2: out of a helicopter, saving all the good guys and
[17:18] Speaker 2: like shooting all the bad guys? Yes. But I don't
[17:20] Speaker 2: look like Chris Helmsworth. And so that's just not going
[17:23] Speaker 2: to happen for me. Right. And I'm aware of that, right?
[17:25] Speaker 2: Unless I write it now. So, so it's like, you know, the,
[17:29] Speaker 2: I think the questions that we ask today are with
[17:32] Speaker 2: the presumption that we have some sort of a magic
[17:34] Speaker 2: wander time machine and we don't. So instead I like
[17:37] Speaker 2: to talk about these stories and laugh at them because
[17:39] Speaker 2: they kind of celebrate both the progress that has been
[17:42] Speaker 2: made and also the stuff that we, the work that
[17:45] Speaker 2: we still need to do. Exactly. So I show up,
[17:48] Speaker 2: I show up at the final audition for Van Wilder.
[17:50] Speaker 2: All I know is it's going to be me and
[17:52] Speaker 2: another guy auditioning for the part of this Indian exchange student.
[17:55] Speaker 2: And we're reading with Ryan Reynolds, who is lovely by
[17:58] Speaker 2: the way, I should say. And I go into the
[18:02] Speaker 2: waiting room and the other guy's already there. And I
[18:04] Speaker 2: remember thinking before I walked in, I was like, who
[18:07] Speaker 2: is it? Like there are a fair amount of Brown
[18:09] Speaker 2: actors in Hollywood. I just, I guess maybe there's one
[18:13] Speaker 2: who I don't know because, you know, you're on text
[18:15] Speaker 2: chains and stuff and share projects and things like that.
[18:18] Speaker 2: So I walk in and it's a white dude in
[18:21] Speaker 2: brown face who has already signed in. And he's sitting
[18:26] Speaker 2: in the waiting room. And I had the following thoughts.
[18:31] Speaker 2: I had the following thoughts. My first thought was, oh, shit.
[18:36] Speaker 1: Okay.
[18:37] Speaker 2: Okay. You've painted your face brown. And I'm like, okay.
[18:41] Speaker 2: All right. So, like, did your agent tell you to
[18:45] Speaker 2: paint your face brown? And if you did, like, did
[18:48] Speaker 2: this dude do it at home or did he do
[18:50] Speaker 2: it in the parking lot, right? Like, before he came up?
[18:54] Speaker 2: And then I was like, if he did it at home,
[18:55] Speaker 2: did he statistically have a higher likelihood of getting pulled
[18:58] Speaker 2: over by the cops or did he not? Yeah. And
[19:01] Speaker 2: I'm just all the things going through my head. And
[19:03] Speaker 2: then I'm like, Ooh, I wonder how his accent is.
[19:05] Speaker 2: It's like, is it? Cause he's going to go in
[19:07] Speaker 2: there and he's going to do one. Right.
[19:08] Speaker 1: Yeah.
[19:09] Speaker 2: And then also, I, I, I don't know if you
[19:11] Speaker 2: relate to this in the same way, but I, I really,
[19:13] Speaker 2: even in those days sort of was like, my beef
[19:17] Speaker 2: is not with this kid because we're desperate man as actors.
[19:24] Speaker 2: You just want to work. You want to get that
[19:26] Speaker 2: credit on your resume. And of course I wasn't like
[19:29] Speaker 2: thrilled that he was doing this, But I remember just
[19:32] Speaker 2: being like, this is a symptom of an institutional challenge
[19:36] Speaker 2: and a problem. And also, in my head, I didn't
[19:40] Speaker 2: say any of this, obviously. It was like, buddy, you
[19:43] Speaker 2: can audition for the new WBCW show where you're playing
[19:47] Speaker 2: Shane from Iowa. Yeah. Gets all the girls. I was like,
[19:53] Speaker 2: this is mine.
[19:54] Speaker 1: Yeah, this is for me. Thank you.
[19:56] Speaker 2: I am booking this audition. And by the way, if
[19:58] Speaker 2: I get it, I am going to do it. Like
[20:00] Speaker 2: all of the hesitation that I had about. whether I
[20:03] Speaker 2: should or shouldn't do it. If I got it, like
[20:04] Speaker 2: all that went out the window, um, fully gone. But
[20:07] Speaker 2: then also what was very cool about the audition. And then,
[20:10] Speaker 2: and then later, um, was like, you know, uh, Ryan
[20:15] Speaker 2: asked me to improvise in the audition. He's like, you're
[20:17] Speaker 2: very funny. Can you, you want to just like run
[20:19] Speaker 2: the scene? Like we'll, we'll just get the bare bones.
[20:22] Speaker 2: And I have, you know, like I'm a trained actor.
[20:24] Speaker 2: I have a background in improv and that was just
[20:26] Speaker 2: such a fun experience. And we kind of continued that
[20:29] Speaker 2: a bunch while we were, uh, making the, making the movie.
[20:33] Speaker 2: So there were things that obviously I, you know, I
[20:35] Speaker 2: had chatted with the producers and changed and tried to
[20:38] Speaker 2: advocate for certain things, you know, out of a list
[20:41] Speaker 2: of a hundred, maybe you only get 20 of the
[20:42] Speaker 2: things that you want, but then the other artistic stuff
[20:45] Speaker 2: that you can add was something that I, I was
[20:47] Speaker 2: very grateful for too, but it's crazy. It's crazy to
[20:50] Speaker 2: think about now.
[20:51] Speaker 1: You know?
[20:51] Speaker 2: Yeah.
[20:52] Speaker 1: We'll be back in just a minute, but here's a
[20:55] Speaker 1: word from our sponsors. This episode is sponsored by BetterHelp.
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[21:17] Speaker 1: And while we're reconsidering old assumptions, maybe there are a
[21:21] Speaker 1: few others worth questioning too. Something I know is true
[21:24] Speaker 1: for me, and so many women I know, is that
[21:27] Speaker 1: we inherit a whole lot of unwritten rules. We absorb
[21:33] Speaker 1: things from culture and society and messaging. And for us,
[21:38] Speaker 1: a lot of them feel contradictory. Be ambitious, but don't
[21:42] Speaker 1: be intimidating. Be there for everyone, but still make time
[21:45] Speaker 1: for yourself and have a 12-step self-care routine.
[21:48] Speaker 2: What?
[21:50] Speaker 1: You're supposed to have it all together, but you can't
[21:52] Speaker 1: look like you're trying too hard. It makes me feel
[21:56] Speaker 1: like my head is spinning And the things we see
[21:58] Speaker 1: in our feed all day tend to reinforce some of them.
[22:02] Speaker 1: I catch myself thinking, well, everyone else seems to be
[22:05] Speaker 1: able to do this. Everyone else is keeping up and
[22:09] Speaker 1: drinking all the water and checking off everything on their
[22:12] Speaker 1: to-do list. And shouldn't I be able to also? I
[22:15] Speaker 1: have to remind myself that it's not a zero-sum game
[22:19] Speaker 1: and also that I can't compare my insides to everyone
[22:23] Speaker 1: else's outsides that I'm seeing online. I would never want
[22:27] Speaker 1: that for a friend, so why do I impose that
[22:29] Speaker 1: kind of pressure on myself, you know? Those are the
[22:32] Speaker 1: kinds of stories that I think therapy can really help
[22:36] Speaker 1: us unpack and then rewrite, which is why I'm excited
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[23:19] Speaker 1: interesting to realize that even in the context of time
[23:23] Speaker 1: where there are things you might or do cringe at,
[23:27] Speaker 1: there was still so much good about it. You know,
[23:31] Speaker 1: I feel that. It's like, I was playing like the
[23:33] Speaker 1: stereotypical hot cheerleader on my first show. And yeah, I
[23:37] Speaker 1: made her into something else over the years, but it's
[23:40] Speaker 1: like the, the opportunity was the opportunity. There weren't, there
[23:44] Speaker 1: weren't the opportunities there are now. And that's just what
[23:48] Speaker 1: it is. You know, when I think about the sort
[23:50] Speaker 1: of the trajectory of your career, like, you know, studio
[23:53] Speaker 1: comedy is a huge leg up for you. Then obviously
[23:56] Speaker 1: Harold and Kumar like changed everything.
[23:59] Speaker 2: Yeah.
[24:00] Speaker 1: What was it about that movie when you read it? Like,
[24:04] Speaker 1: did you know at the time it would be huge
[24:07] Speaker 1: or did you feel like it was another step in
[24:10] Speaker 1: the right direction in terms of the next job?
[24:14] Speaker 2: I read that script and laughed harder than I had
[24:19] Speaker 2: laughed at reading a script. And I'm, I generally, when
[24:22] Speaker 2: I read, I don't, um, I don't emote out loud. Yeah. Like,
[24:27] Speaker 2: I'll laugh, but in my head, I was laughing out loud,
[24:30] Speaker 2: like verbally laughing out loud at this script. Um, and
[24:35] Speaker 2: I remember actually, so John Hurwitz and Hayden Schlossberg, the
[24:38] Speaker 2: two guys who wrote Harold and Kumar go to White Castle,
[24:40] Speaker 2: all the three Harold and Kumar movies.
[24:41] Speaker 1: Um, and a fourth, if we get casual two sequels
[24:44] Speaker 1: and maybe another on the way.
[24:46] Speaker 2: So they, uh, I met them before they sold the script.
[24:50] Speaker 2: It was a couple months before I think, and there was, um,
[24:53] Speaker 2: we had a mutual friend who had a birthday party
[24:55] Speaker 2: and that friend was like, Hey, and by the way,
[24:58] Speaker 2: these were all like, they were assistants or something at
[25:01] Speaker 2: the time trying to get their screenwriting career up and running.
[25:04] Speaker 2: And our friend was like, Hey, you should, um, you
[25:06] Speaker 2: should meet John and Hayden. They're, they're, uh, they're good guys. Um,
[25:11] Speaker 2: they're big fans of yours from Van Wilder. Uh, And
[25:15] Speaker 2: you should hear about the script they have. They give
[25:16] Speaker 2: me just the bare bones about the story. And I
[25:19] Speaker 2: was like, oh, man, this is amazing. I'd love to
[25:21] Speaker 2: read it. You're never going to sell it in Hollywood
[25:24] Speaker 2: to a studio. But maybe we can all find... Venture
[25:28] Speaker 2: Capital was booming in the Bay Area. And maybe we
[25:31] Speaker 2: can find the right people to invest in this and
[25:34] Speaker 2: do a low-budget version. And they looked at me like
[25:36] Speaker 2: I was crazy. And they were like, no, no, no.
[25:38] Speaker 2: We're going to sell this to a studio. We're making...
[25:43] Speaker 2: we're making a movie. And I was like, look, I, I, um,
[25:47] Speaker 2: let me read it. Send it to me. They sent
[25:48] Speaker 2: it to me that week. I read it. Like I said,
[25:50] Speaker 2: laughed out loud, called them, reiterated that they were not
[25:52] Speaker 2: going to sell this to a major studio because it,
[25:54] Speaker 2: it featured two Asian American men in lead roles in
[26:00] Speaker 2: a studio comedy. And I just, up until that point,
[26:03] Speaker 2: everything I had been told was like, that just doesn't
[26:06] Speaker 2: happen or it's not going to happen. And they go, Cal, um,
[26:10] Speaker 2: we are making a movie called Harold and Kumar go
[26:12] Speaker 2: to White Castle. I understand that you've had friends who
[26:14] Speaker 2: have written scripts with performers of color, characters of color,
[26:18] Speaker 2: and they were told that somebody would buy it as
[26:19] Speaker 2: long as they changed them to make them white characters.
[26:22] Speaker 2: We are making Harold and Kumar go to White Castle.
[26:24] Speaker 2: We are not making David and Jason go to McDonald's.
[26:27] Speaker 2: I was like, okay, that's hilarious.
[26:29] Speaker 1: All right.
[26:30] Speaker 2: Sure. And then sure enough, a couple of weeks later,
[26:32] Speaker 2: they sold the script to a company that had a
[26:36] Speaker 2: deal with the new line and, and, and, I guess Lionsgate,
[26:39] Speaker 2: Warner Brothers, depending on who bought who at which time.
[26:42] Speaker 1: You're right.
[26:43] Speaker 2: But it was, and then began this really long process
[26:47] Speaker 2: of auditioning because they auditioned people, you know, obviously in
[26:51] Speaker 2: New York and LA, but Vancouver and London and South Africa.
[26:56] Speaker 2: So we didn't know, and it didn't have a huge
[26:58] Speaker 2: budget when we made it. We thought the script was
[27:00] Speaker 2: really funny. The movie comes out and it, everybody forgets
[27:04] Speaker 2: it really tanked at the box office. Like it did
[27:07] Speaker 2: not do well at all. And it got pulled after
[27:09] Speaker 2: its initial, whatever, it's a week or two commitment and
[27:12] Speaker 2: it's run. And then all the calls that I had
[27:16] Speaker 2: with like my then manager and agent were like, yeah,
[27:19] Speaker 2: don't expect the phone to ring for a while. You know,
[27:21] Speaker 2: you guys kind of bombed this movie. And the talk
[27:24] Speaker 2: around town is, see, we told you that two Asian
[27:26] Speaker 2: American men can't open a studio comedy, right? And in
[27:30] Speaker 2: my head, I was like, I feel like this is
[27:33] Speaker 2: not true. I feel like, They were underestimating their audience,
[27:37] Speaker 2: but I guess they're right. Like if people didn't show
[27:39] Speaker 2: up in the theaters, maybe nobody wants to see a
[27:42] Speaker 2: movie like this unless the characters are white or black.
[27:46] Speaker 2: And then two months, I think it was two months later,
[27:49] Speaker 2: the movie comes out on HBO and on DVD with
[27:51] Speaker 2: zero marketing budget. And fans just found it on their own. Yes.
[27:55] Speaker 2: And they bought the DVD and it was not just
[27:58] Speaker 2: the New York's and LA's and San Francisco's. It was
[28:00] Speaker 2: like Oklahoma and Iowa and the deep South. And people
[28:05] Speaker 2: enjoyed this movie and bought it in droves because they just,
[28:09] Speaker 2: it reminded them of friends of theirs and they wanted
[28:10] Speaker 2: to go on this kind of funny journey with them.
[28:13] Speaker 2: And that was really redemptive, I think for us, because
[28:17] Speaker 2: it was a redemptive because I'm like, see, we can
[28:19] Speaker 2: open a movie and have it do well. And second,
[28:23] Speaker 2: it also just, I mean, I don't know how you feel,
[28:26] Speaker 2: but I try to separate like my art from the
[28:30] Speaker 2: politics of things, but it was one of the first
[28:32] Speaker 2: feelings I had where I felt redemption that the way
[28:35] Speaker 2: that Hollywood then was dumbing down its audience and saying
[28:40] Speaker 2: white audiences don't want to see two funny people of color.
[28:44] Speaker 2: I just, in my heart felt like that was wrong.
[28:46] Speaker 2: And to prove that wrong, Was really great because we
[28:49] Speaker 2: all love to laugh. And I'm glad that those movies
[28:51] Speaker 2: have a huge fan base of people across the political spectrum.
[28:56] Speaker 2: Like the beauty that's left in what we do that
[28:59] Speaker 2: is still there in such a polarizing world. Not to
[29:02] Speaker 2: make Harold and Kumar more than it should be about,
[29:04] Speaker 2: but it's a good feeling to know that, you know,
[29:07] Speaker 2: that that all exists.
[29:09] Speaker 1: I don't think it's making it more. I think it's
[29:11] Speaker 1: just being aware of you know, every sort of layer
[29:16] Speaker 1: of the systems that we live in. For our friends
[29:19] Speaker 1: at home, I'm pretty sure the first time we had
[29:23] Speaker 1: overlap in the political system was in 08. But I
[29:29] Speaker 1: remember being at a specific event with you in 2012.
[29:33] Speaker 1: And I don't know, your whole thing you know, the
[29:40] Speaker 1: fact that you not only were really dedicated to trying
[29:44] Speaker 1: to get young people to care about progressive values and,
[29:48] Speaker 1: you know, policies that would actually benefit them, but like
[29:51] Speaker 1: you actually took a break from acting and went and
[29:53] Speaker 1: worked in the white house. Like, Hello? How did the
[29:58] Speaker 1: whole thing happen for you? How did you even do that?
[30:03] Speaker 2: I'll give you the kind of, I guess, semi-abridged. How
[30:05] Speaker 2: are we on time? Like the TLDR? I tend to over-talk. Yeah, yeah, yeah. Exactly, exactly.
[30:10] Speaker 1: I'm a talker.
[30:11] Speaker 2: Me too. So in 07 and 08, I was on
[30:17] Speaker 2: this medical drama house. Olivia Wilde was on house with
[30:22] Speaker 2: me at the time. And she knocked on my dressing
[30:25] Speaker 2: room door And she goes, hey, I have a plus
[30:28] Speaker 2: one to a Barack Obama event. Do you want to come?
[30:32] Speaker 2: And this was October of 2007. So what that means
[30:34] Speaker 2: is there were like 12 Democrats and 12 Republicans each
[30:38] Speaker 2: running for president. It was the primaries before the primaries.
[30:42] Speaker 2: And nobody really knew Obama. They were like, oh, yeah,
[30:45] Speaker 2: he's the young black senator from Illinois. We like his
[30:48] Speaker 2: speech from 2004. And that's how I felt, too. And
[30:51] Speaker 2: I was like, oh, I'm good, Olivia. You enjoyed that event.
[30:56] Speaker 2: She's like, no, I mean, I have a plus one.
[30:58] Speaker 2: I think you'd like it. And I was like, yeah,
[31:00] Speaker 2: but it's probably like a recruitment event, right, for his campaign.
[31:04] Speaker 2: And she's like, yeah. And I was like, yeah, no,
[31:07] Speaker 2: I'm good. And she goes, well, I saw you reading
[31:09] Speaker 2: his book. And I was like, yeah, I also read
[31:11] Speaker 2: a book about Dick Cheney. Don't need to meet him.
[31:13] Speaker 2: It's like I like to read. And she kept pushing
[31:18] Speaker 2: for a couple of days, and I think like the
[31:19] Speaker 2: third or fourth day she's like, by the way, it's
[31:22] Speaker 2: an open bar. I just think it, I'm like sold, sold.
[31:25] Speaker 1: Done.
[31:25] Speaker 2: Let's go. So we go and it was like a
[31:28] Speaker 2: hundred people. And it was like, you know, Olivia, I
[31:32] Speaker 2: think it was like Justin Timberlake, Usher. There were people
[31:35] Speaker 2: like this who were invited and I figured, okay, if
[31:39] Speaker 2: it's going to be a hundred artists, basically somebody is
[31:41] Speaker 2: going to ask really good questions about arts policy and
[31:44] Speaker 2: public art funding and things like that. So maybe I'll
[31:48] Speaker 2: ask a different question. So I went home. And before
[31:51] Speaker 2: this event, I was like looking up the Obama website, like, oh,
[31:54] Speaker 2: there's a section on climate change. And I read about how, oh,
[31:58] Speaker 2: Obama wants to invest in corn to turn into ethanol.
[32:02] Speaker 2: And I remembered, this is what a nerd I am.
[32:04] Speaker 2: I remembered this article that I had read shortly before
[32:07] Speaker 2: that in Foreign Affairs Magazine, the like thick blue thing
[32:11] Speaker 2: that you have to read in college. I still subscribe
[32:13] Speaker 2: to it. So I remember there was this article that
[32:16] Speaker 2: was like, oh, you know, if we invest too heavily
[32:19] Speaker 2: in corn... to turn into biofuels, then it'll drive the
[32:22] Speaker 2: price of corn up for people who rely on it
[32:25] Speaker 2: in developing countries. And so I'm like, well, then why
[32:29] Speaker 2: would he do this? This is a great question to ask.
[32:32] Speaker 2: So I had that in the back of my head,
[32:35] Speaker 2: go to this event with Olivia, Obama's making the rounds.
[32:38] Speaker 2: I have like six glasses of wine. Like it is
[32:41] Speaker 2: because I'm like, whatever, I'm obviously not signing up to
[32:43] Speaker 2: volunteer for this guy's presidential campaign. But there's like free
[32:47] Speaker 2: booze and it's a room full of fellow artists. Like
[32:49] Speaker 2: what's not to love? This is great. And Obama comes
[32:52] Speaker 2: over and says hi to me and Olivia. And I
[32:54] Speaker 2: was like, oh, that's right, my question. Senator, you know,
[32:59] Speaker 2: I read on your website that you're investing in corn
[33:02] Speaker 2: to turn into ethanol. But isn't that just going to
[33:04] Speaker 2: drive up the price of corn for people who rely
[33:07] Speaker 2: on it in developing countries? And Obama gives me what
[33:10] Speaker 2: now the whole world knows is his like cocky smile.
[33:14] Speaker 2: And he gives me this really cocky smile and he goes, oh, well, look,
[33:19] Speaker 2: a couple of things. A, I read that article in
[33:21] Speaker 2: Foreign Affairs, too. And if you had read my campaign
[33:26] Speaker 2: website carefully, you would have seen that I'm proposing investing
[33:30] Speaker 2: in corn-based ethanol as a bridge to cellulosic ethanol so
[33:35] Speaker 2: that we can one day create biofuels from the grass
[33:38] Speaker 2: that grows in our yards. And when you rake your
[33:40] Speaker 2: front lawn... of leaves. And he just gives me another
[33:43] Speaker 2: cocky smile and walks away. And Olivia was like, you
[33:45] Speaker 2: just got schooled by Barack Obama. And we both signed
[33:49] Speaker 2: up to volunteer for his campaign that night. So I
[33:52] Speaker 2: was like, all right, you got me. I'll do a,
[33:55] Speaker 2: I'll do a trip to Iowa for you. So that
[33:58] Speaker 2: was kind of the intro. I think a lot of us,
[34:01] Speaker 2: a lot of artists at the time in the 07, 08,
[34:05] Speaker 2: the two biggest, they call them surrogates where you speak
[34:08] Speaker 2: on behalf of a candidate. And I think There were
[34:10] Speaker 2: a lot of people who did this for Hillary in
[34:12] Speaker 2: the early states, a lot of people who did this
[34:14] Speaker 2: for Obama in the early states. And then some of
[34:16] Speaker 2: the other candidates, I think the more, I don't want
[34:19] Speaker 2: to say fringe, but the less viable candidates had their
[34:21] Speaker 2: own sprinkling of people. So I did that for like
[34:24] Speaker 2: a year, over a year, I guess, and then joined
[34:28] Speaker 2: the Obama Arts Policy Committee. And by the time the
[34:32] Speaker 2: campaign was over, I applied for a job on this
[34:35] Speaker 2: like web link website. this white house job where I
[34:38] Speaker 2: was like, I am just curious if I'm even remotely
[34:41] Speaker 2: qualified to do this. Like I had gone to grad
[34:44] Speaker 2: school for, uh, international security and I did, I didn't
[34:48] Speaker 2: really tell anybody about it. It was not a full masters.
[34:51] Speaker 2: It was like a little, it's a thing you could
[34:53] Speaker 2: do online mostly. Okay.
[34:56] Speaker 1: I've not done it, but okay.
[34:58] Speaker 2: I'm a big nerd. I wanted to see like, are,
[35:00] Speaker 2: do any of these things matter? These things that I
[35:02] Speaker 2: did because I wanted to. Um, and, uh, and nobody called.
[35:08] Speaker 2: Nobody called me after I submitted my resume and my
[35:11] Speaker 2: CV onto this website after Obama won. And I only
[35:15] Speaker 2: told my then manager, my Hollywood manager that I had applied.
[35:21] Speaker 2: And he was like, well, that's crazy, don't you think?
[35:22] Speaker 2: I was like, yeah, I'm obviously not getting a White
[35:24] Speaker 2: House job. I just wanted to see if I was qualified.
[35:27] Speaker 2: I was like, well, did they say anything? Did you
[35:29] Speaker 2: get any feedback? I was like, no, but they must
[35:31] Speaker 2: be getting so many applications, right? Yeah. Then right before inauguration,
[35:35] Speaker 2: right before Obama's inauguration, I get this phone call that says, hey,
[35:39] Speaker 2: will you be part of the inaugural ceremony? There's a
[35:42] Speaker 2: concert on the steps of the Lincoln Memorial and there
[35:44] Speaker 2: are artists who are doing mini speeches about the state
[35:48] Speaker 2: of democracy and then people who are singing. So it's
[35:50] Speaker 2: like Bruce Springsteen and Queen Latifah and people like that.
[35:53] Speaker 1: Casual.
[35:54] Speaker 2: Very casual. So I got to read a quote, as
[35:57] Speaker 2: did like Jack Black and some really funny people I admire.
[36:00] Speaker 2: The perk of doing this, the perk of saying yes,
[36:02] Speaker 2: was that backstage you got to introduce your family and
[36:05] Speaker 2: friends to the new now first family. And so I
[36:09] Speaker 2: brought my parents and my brother and my manager and, uh,
[36:12] Speaker 2: and you know, the, the president said hello and he said, Oh,
[36:16] Speaker 2: thanks so much for all the work you did. And
[36:18] Speaker 2: then Mrs. Obama, who I hadn't really met before comes
[36:21] Speaker 2: through and she goes, Cal, it's great to meet you. Um,
[36:25] Speaker 2: I know all the stuff you did for the campaign.
[36:27] Speaker 2: I hope you stay involved. And I assume this is
[36:29] Speaker 2: something that Michelle Obama says to everybody. So I said,
[36:32] Speaker 2: Of course, I definitely plan to. And my manager, who
[36:36] Speaker 2: I describe as like every character from the HBO show
[36:39] Speaker 2: Entourage in one person. So just like the former manager
[36:45] Speaker 2: says to Michelle Obama, well, you know, Cal applied for
[36:49] Speaker 2: a job, right? And she's like, what? And I'm like, no, no, no, no, no.
[36:53] Speaker 2: You don't, don't do this. Don't do this. This is not,
[36:55] Speaker 2: this is not like, this is not a Warner Brothers
[36:57] Speaker 2: casting office. You don't do this. And she goes, what
[37:00] Speaker 2: do you mean? And he goes, yeah, yeah. He applied
[37:02] Speaker 2: for a job and nobody even called him back. And
[37:06] Speaker 2: I am humiliated. And she goes, well, who did you
[37:09] Speaker 2: apply with? And I just blurt out, well, I didn't
[37:13] Speaker 2: want to bother anybody. So I just put my application
[37:15] Speaker 2: on the website. And she looks at me like I
[37:18] Speaker 2: was insane. Like you just cold dropped your CV on
[37:22] Speaker 2: a website and didn't call anybody. So then she goes, hey, Barack,
[37:26] Speaker 2: come here. And like summons the president back over and goes,
[37:29] Speaker 2: tell him what you just told me. And I was like, well, sorry,
[37:33] Speaker 2: I applied for a job at the White House in
[37:34] Speaker 2: case I'm qualified, blah, blah, blah. And he said the
[37:36] Speaker 2: same thing. He's like, who did you apply with? And
[37:39] Speaker 2: I was like, well, I didn't want to bother anybody.
[37:41] Speaker 2: How am I supposed to know who to call? Well,
[37:44] Speaker 2: so his point was, he looked at me and he goes,
[37:46] Speaker 2: why wouldn't you just call somebody? And at that point,
[37:50] Speaker 2: I recognized what you know, because you're also an early
[37:52] Speaker 2: supporter of a lot of candidates, is that if you
[37:55] Speaker 2: start volunteering on a campaign early, I had spent time
[38:01] Speaker 2: with Barack Obama on the campaign trail. And I knew
[38:04] Speaker 2: his senior advisors. And that's the reason that I'd worked
[38:07] Speaker 2: in 26 states by that point. Yes, I was good
[38:10] Speaker 2: at my job that I was doing, but you do
[38:12] Speaker 2: know these people. And so his point was like, he
[38:15] Speaker 2: was confused whether I was actually serious about that application
[38:18] Speaker 2: or not. Because if you don't call anybody, by the way,
[38:22] Speaker 2: the point of that is, so I got a call
[38:24] Speaker 2: later that week from somebody who said, look, we're actually
[38:28] Speaker 2: looking for, we have one salary to pay, but we're
[38:32] Speaker 2: looking for somebody in the public engagement outreach office to
[38:35] Speaker 2: cover outreach to young Americans, outreach to the Asian American
[38:39] Speaker 2: Pacific Islander community, and outreach to the arts community. And
[38:44] Speaker 2: you taught college, you did youth outreach for us, and
[38:47] Speaker 2: you're an artist and understand that community well. Perfect job
[38:51] Speaker 2: for me. So it just so happened that the timing
[38:52] Speaker 2: was right. But the big lesson from that was in
[38:56] Speaker 2: their eyes, they were... Think about it this way. Anybody
[38:59] Speaker 2: who's listening who has a more traditional job, or any job, frankly,
[39:02] Speaker 2: if you want a job at a particular company, most
[39:05] Speaker 2: actors don't use LinkedIn or anything, but the way that
[39:08] Speaker 2: people use LinkedIn, you're going through your LinkedIn to see
[39:10] Speaker 2: how many degrees of separation you have from somebody who
[39:12] Speaker 2: works at a particular company. You're going to make those
[39:15] Speaker 2: phone calls. You know that dropping a resume onto an
[39:18] Speaker 2: aggregator website is only going to mean that some AI
[39:22] Speaker 2: slop tries to filter through for who has the supposed qualifications, right?
[39:28] Speaker 2: So you got to call the people. You always have
[39:30] Speaker 2: to call humans.
[39:31] Speaker 1: And I know you're talking to like young people with
[39:33] Speaker 1: jobs who are listening, but I also feel like you're
[39:35] Speaker 1: reminding me, I hate doing that.
[39:38] Speaker 2: Me too.
[39:39] Speaker 1: I hate to call people. I hate to bother people.
[39:41] Speaker 1: I'm like, you know, I'm a fan. I'm here. And
[39:44] Speaker 1: that's not the way to get anything done.
[39:45] Speaker 2: Nope. I hate Ugh. This is how I had always felt.
[39:49] Speaker 1: I hate it.
[39:50] Speaker 2: It really did. It doesn't feel right, I think. Maybe
[39:52] Speaker 2: it's a generational thing for us or maybe it's just
[39:55] Speaker 2: being too nice. I don't know.
[39:57] Speaker 1: But did this, like did this lesson and then working
[40:00] Speaker 1: in the White House and literally being in charge of outreach,
[40:04] Speaker 1: did it change that tendency in you at all?
[40:08] Speaker 2: I think it made me a little more pragmatic for
[40:10] Speaker 2: certain things. So I'll give you an example. You know,
[40:12] Speaker 2: it's funny you're asking me this. I was just telling
[40:14] Speaker 2: a friend and I wondered, I wondered when I was
[40:16] Speaker 2: telling a friend this story. So I guest hosted two
[40:21] Speaker 2: weeks on The Daily Show after Trevor left.
[40:24] Speaker 1: Such a dream come true.
[40:25] Speaker 2: Loved it. It was awesome. The first week was, I think,
[40:29] Speaker 2: when they had like 18 guest hosts or something. And
[40:32] Speaker 2: then they whittled it down several months later and had
[40:35] Speaker 2: like five or six of us come back to host
[40:37] Speaker 2: a second week. And in the middle of that, I
[40:40] Speaker 2: remember calling my agents at UTA and And thinking to myself,
[40:45] Speaker 2: I guess I know this from the Michelle Obama conversation,
[40:49] Speaker 2: but really I've watched enough succession to know that like
[40:55] Speaker 2: you should just ask somebody to go to drinks.
[40:59] Speaker 1: Yeah.
[41:00] Speaker 2: As an adult human and have a conversation. And if
[41:04] Speaker 2: they say no to the drinks, that's fine. If the
[41:07] Speaker 2: drinks don't go well or they go well and it
[41:09] Speaker 2: doesn't yield what you want, also fine. Yeah. But like,
[41:11] Speaker 2: why not? Why wouldn't you do that? It's like kind
[41:14] Speaker 2: of old school, but also if you like people, just
[41:18] Speaker 2: do it that way. So I had invited a couple
[41:20] Speaker 2: of the execs who were ultimately going to make the
[41:22] Speaker 2: Daily Show decision out to drinks. And I basically made
[41:24] Speaker 2: my case where I said, I'd love this job. I
[41:28] Speaker 2: am the only guest host who's not a stand-up comedian.
[41:32] Speaker 2: So I understand you might have qualms about that, but
[41:35] Speaker 2: I'm also the only guest host who's worked in the
[41:37] Speaker 2: executive branch in politics. So I think there's a value
[41:41] Speaker 2: add there, too. Anyway, at the end of drinks, like
[41:44] Speaker 2: the following day, I get this call that's like, you're
[41:46] Speaker 2: guest hosting a second week on The Daily Show. So
[41:49] Speaker 2: I didn't ultimately get the gig. They brought Jon Stewart back.
[41:51] Speaker 2: They're doing this amazing rotating thing with all of their
[41:54] Speaker 2: hilarious correspondents. So sure. Did it ultimately not go my way? Yes.
[41:58] Speaker 2: Did I get two of the most amazing weeks? One
[42:01] Speaker 2: being an additional one because I advocated for myself in
[42:04] Speaker 2: a particular way. Yes. But I don't know if that
[42:06] Speaker 2: was thanks to Michelle Obama teaching me a lesson or
[42:09] Speaker 2: just watching Succession. Right. Maybe a little bit of both. Yeah,
[42:12] Speaker 2: a little both.
[42:13] Speaker 1: And now a word from our sponsors who make this
[42:15] Speaker 1: show possible. How do you think about that stuff? Cause you're,
[42:28] Speaker 1: you know, you're talking about what sort of advocacy and
[42:31] Speaker 1: activism has the most real impact. You obviously had quite
[42:37] Speaker 1: an impact working in the white house, but then you
[42:40] Speaker 1: also got to the point where you were ready to
[42:43] Speaker 1: step back and go back into your personal world, into
[42:46] Speaker 1: your personal life, you know, writing and making movies and
[42:49] Speaker 1: eventually doing your book and like hat, How did you
[42:52] Speaker 1: decide when it was the right time to fill your
[42:55] Speaker 1: cup as an individual after you'd been sort of filling,
[42:59] Speaker 1: you know, the social cup for so long?
[43:01] Speaker 2: I think, I mean, you know, going off and working,
[43:05] Speaker 2: working in the Obama administration was just one of those
[43:07] Speaker 2: things where I thought, oh, I, the decision to apply even,
[43:12] Speaker 2: I kind of thought, well, I just spent the last
[43:14] Speaker 2: like 16 months going to 26 states to tell people
[43:18] Speaker 2: that they should support this guy. And now I'm just
[43:20] Speaker 2: going to go back to, you know, my fancy TV job,
[43:23] Speaker 2: which by the way, loved and would happily do again, uh,
[43:29] Speaker 2: have the job, not leave it necessarily.
[43:31] Speaker 1: Yeah.
[43:34] Speaker 2: But I remember thinking like, if I am qualified to
[43:36] Speaker 2: do this, then, then maybe there's an opportunity to kind
[43:39] Speaker 2: of just see if I can help get the thing
[43:41] Speaker 2: done that I promised that this guy would get done
[43:44] Speaker 2: because you know, you need teams and teams of people to,
[43:46] Speaker 2: kind of help with that. And I thought it was
[43:48] Speaker 2: the right thing at the time. And then when it
[43:50] Speaker 2: actually came to fruition, I kind of thought like, Oh,
[43:53] Speaker 2: this is, you know, what a selfishly, what a historic
[43:55] Speaker 2: thing to be part of. And yes, there's no reason
[43:57] Speaker 2: to say no. And on your deathbed, are you going
[43:59] Speaker 2: to be like, I'm so glad I didn't work for
[44:01] Speaker 2: the first black president and get some healthcare passed, you know,
[44:05] Speaker 2: be like, no, I think I might be like, Oh,
[44:07] Speaker 2: this TV career was amazing. And I never left it,
[44:10] Speaker 2: but I wish maybe I had taken a short sabbatical.
[44:13] Speaker 2: I thought I was only going to do a year.
[44:15] Speaker 2: And that's what I wanted to do. I wanted to
[44:16] Speaker 2: step away from a year and then come right back
[44:19] Speaker 2: to acting. And the reason it took almost two and
[44:22] Speaker 2: a half is within the first year, I realized almost
[44:25] Speaker 2: in those days, you have to just remember, almost nothing
[44:29] Speaker 2: gets done quickly in politics. That's generally the sign of
[44:32] Speaker 2: a healthier democracy. What you're seeing right now is clearly
[44:35] Speaker 2: not a healthy democracy, which is why executive action is
[44:38] Speaker 2: so prevalent. Yeah. But I'm like, oh, right. I've been
[44:42] Speaker 2: here almost a year and we still don't have Don't Ask,
[44:45] Speaker 2: Don't Tell repealed. I think we had the ACA. There
[44:49] Speaker 2: was no, the DREAM Act was still something that was
[44:52] Speaker 2: going to be voted on. And I'd been working on
[44:55] Speaker 2: all of those just as part of the youth, particularly
[44:57] Speaker 2: youth outreach components. So I stayed until the things that
[45:01] Speaker 2: were on that legislative list were going to be done.
[45:04] Speaker 2: I'm like, if they're not done in another year, I'm
[45:07] Speaker 2: definitely leaving regardless because I got to go back to
[45:09] Speaker 2: my actual career. I am not working in politics for
[45:12] Speaker 2: the rest of my life. Um, so that's when I
[45:14] Speaker 2: decided to come back and, and, uh, amazing first gig.
[45:17] Speaker 2: I like, I leave the white house and a couple
[45:19] Speaker 2: of weeks later, I'm on the new season of how
[45:21] Speaker 2: I met your mother. And I'm like, I'm back with
[45:22] Speaker 2: my people.
[45:23] Speaker 1: Incredible. So incredible. I love it. Well, and now, you know,
[45:28] Speaker 1: fast forward to today. your latest role, which must make
[45:32] Speaker 1: your parents so happy. I know it did when I
[45:35] Speaker 1: did this. The movie, trust me, I'm a doctor.
[45:39] Speaker 2: Yeah.
[45:39] Speaker 1: You get to play a doctor on screen.
[45:42] Speaker 2: I do.
[45:42] Speaker 1: But yours is not, you know, total fiction. It's not
[45:47] Speaker 1: a created thing. You're portraying the real life doctor whose
[45:51] Speaker 1: world kind of got knocked sideways by the death of
[45:54] Speaker 1: Anna Nicole Smith.
[45:55] Speaker 2: It's a crazy story.
[45:57] Speaker 1: Can you, like, can you give us I don't want
[46:00] Speaker 1: to spoil anything, but also I'm like, tell the people
[46:03] Speaker 1: what this is all about.
[46:04] Speaker 2: Yeah, I won't spoil it, but yeah. Have you played
[46:09] Speaker 2: a real person who's still living, by the way?
[46:11] Speaker 1: I don't think so. That's got to be wild.
[46:13] Speaker 2: It was wild. This is the first time that I
[46:15] Speaker 2: have had the chance to do that. I've played characters
[46:18] Speaker 2: from book adaptations and things like that. Yeah. Obviously played
[46:21] Speaker 2: characters based on 10 real people. And you do the
[46:25] Speaker 2: research that way, but this is the first time there
[46:27] Speaker 2: was an actual person. And, and Anna Nicole Smith, who
[46:30] Speaker 2: was a model and reality TV star who tragically passed
[46:33] Speaker 2: away in the, in the two thousands. She hurt her doctor.
[46:38] Speaker 2: I believe her lawyer and somebody else. There were three
[46:43] Speaker 2: people who were on trial in connection with her death.
[46:47] Speaker 2: One of whom is, is her doctor, this guy named
[46:49] Speaker 2: Sandeep Kapoor. And, and, he, he wrote a book 10
[46:56] Speaker 2: years after this whole ordeal from his perspective about what
[47:01] Speaker 2: being put on trial was like, um, then ends up
[47:06] Speaker 2: randomly like kind of selling, selling it to this writer, director,
[47:12] Speaker 2: producer pair, um, who turned it into this film. And
[47:16] Speaker 2: I remember reading the script a couple of years ago
[47:18] Speaker 2: being like, isn't this guy in prison? And he is
[47:22] Speaker 2: not right. This just shows you how, yes, you were,
[47:26] Speaker 2: if you're, if you remember the 15 years ago, TMZ
[47:29] Speaker 2: people magazine, all the like stuff I'm like, Oh yeah,
[47:32] Speaker 2: I remember seeing this with one part of my brain, but.
[47:35] Speaker 1: Like guilty and it's like, wait, no, Oh my God,
[47:37] Speaker 1: I'm so sorry.
[47:38] Speaker 2: Yeah, exactly. And then there's more to the story. So, uh,
[47:41] Speaker 2: so I, I read the script. I'm like, Oh, I
[47:43] Speaker 2: had no idea it was this dynamic. I agreed to
[47:45] Speaker 2: do it. And then the real Dr. Kapoor was kind
[47:48] Speaker 2: enough to let me shadow him. And he's a really quirky,
[47:52] Speaker 2: very peculiar in a, in a, in a like very
[47:55] Speaker 2: loving way guy. And the first thing that I recognized
[48:00] Speaker 2: was like, I shadowed him. He still has the same
[48:01] Speaker 2: practice in LA that he had when Anna Nicole was,
[48:05] Speaker 2: was his patient, but he bought it from an older
[48:09] Speaker 2: doctor who was retiring. And she was a patient of
[48:12] Speaker 2: the older doctor and, So when you buy a medical practice,
[48:15] Speaker 2: you're also buying your patient list. So that's how he
[48:18] Speaker 2: inherited the patient. But the first thing you notice when
[48:21] Speaker 2: you shadow him is that, you know, like, I don't
[48:25] Speaker 2: know who your doctors are here, but if I need
[48:27] Speaker 2: to make an appointment with my doctor, I can't really
[48:30] Speaker 2: call a human. By the time I get a human,
[48:33] Speaker 2: it takes a long time. I can go online. And
[48:36] Speaker 2: hope that there's something in the next seven weeks where
[48:39] Speaker 2: I can get a slot in. Like it's ludicrous, right?
[48:42] Speaker 2: This guy, you call him, there's a human who picks
[48:45] Speaker 2: up the phone. There are like three receptionists and he
[48:48] Speaker 2: knows you when you come in. It's like the old
[48:51] Speaker 2: 1950s family doctor vibe. So as soon as I saw that,
[48:54] Speaker 2: I kind of thought now I understand how for a
[48:58] Speaker 2: cynical American palate, Right. Right. so well or that you
[49:11] Speaker 2: went to your patient's birthday parties or things like that
[49:14] Speaker 2: but then you see how he works and I'm like
[49:15] Speaker 2: I guess if I had that relationship with my doctor
[49:17] Speaker 2: like yeah you'd get the you'd get the invite to
[49:20] Speaker 2: like the Super Bowl party or you'd get the thing
[49:23] Speaker 2: that's like yeah come on over so I think the
[49:26] Speaker 2: movie explores a lot of these blurred lines between him
[49:29] Speaker 2: and Anna Nicole and it was just it was really
[49:32] Speaker 2: interesting to play around with that it's a dark comedy
[49:35] Speaker 2: I almost hesitate saying that because I never want to
[49:36] Speaker 2: make light of something that came out of somebody's tragic
[49:39] Speaker 2: death but It was a super interesting thing to work on.
[49:43] Speaker 2: I'm glad it's finally coming out.
[49:44] Speaker 1: It's really exciting. I also think, you know, I understand
[49:49] Speaker 1: the hesitation to describe something as a dark comedy that
[49:51] Speaker 1: does revolve around real people when there was a tragedy involved.
[49:56] Speaker 1: But I also think it's an interesting way in.
[49:58] Speaker 2: Yeah, for sure.
[49:59] Speaker 1: In terms of the container of it. It's like it
[50:04] Speaker 1: allows for certain things to come across that I think
[50:08] Speaker 1: other people um, traditional devices might not. And so it, it,
[50:13] Speaker 1: it really does work. And I think because it is,
[50:15] Speaker 1: you know, more his story, it, it makes sense because
[50:20] Speaker 1: what a, what a strange, um, just what a strange
[50:24] Speaker 1: thing to kind of get yanked out of your daily
[50:26] Speaker 1: life by, you know, and I think about even the era,
[50:31] Speaker 1: you know, the, the early two thousands and the, the
[50:34] Speaker 1: paparazzi and the, the advent of all those terrible, uh,
[50:38] Speaker 1: tabloid sites and just, oh, it was just all so
[50:41] Speaker 1: gross and terrible, terrible for everybody. And I don't know,
[50:47] Speaker 1: thinking about what public perception felt like then, what it
[50:50] Speaker 1: feels like now, you know, now the opinions of you
[50:52] Speaker 1: can be sort of swayed online by bot farms people
[50:56] Speaker 1: can pay for. It's like everything is so nuts. You know,
[51:00] Speaker 1: it's nice to have this opportunity to be reminded to
[51:05] Speaker 1: look a little deeper at somebody's story.
[51:07] Speaker 2: Definitely. There's a lot of complexity and there are a
[51:09] Speaker 2: lot of flaws there. I mean, the other part that
[51:11] Speaker 2: I loved about playing him is he's a flawed character
[51:15] Speaker 2: in this story in a way that I think we
[51:18] Speaker 2: ultimately will kind of, he'll make you angry, but you'll
[51:21] Speaker 2: also empathize because nobody is straightforward. We all make mistakes.
[51:25] Speaker 1: Oh, I love it. And I'm thrilled that it's out
[51:27] Speaker 1: in the world as well.
[51:28] Speaker 2: Thank you.
[51:29] Speaker 1: Before I let you go today, I have to ask
[51:32] Speaker 1: you my favorite question that I ask everybody, which is
[51:36] Speaker 1: what feels like your work in progress right now?
[51:39] Speaker 2: Oh, great question. I'll just be a little vulnerable, I guess. Pre-COVID,
[51:46] Speaker 2: I feel like I was kind of on more of
[51:49] Speaker 2: a role creatively in a way that felt grounded for me.
[51:52] Speaker 2: I had a show on the air and I was
[51:55] Speaker 2: developing a couple of other things and Most of this
[51:58] Speaker 2: is also just the marketplace and how people were traditionally
[52:02] Speaker 2: buying still up until after COVID and the strikes and
[52:05] Speaker 2: all of that. So the one thing that I think
[52:07] Speaker 2: is a work in progress is I have a couple
[52:09] Speaker 2: of things that I'm pitching and that I'm writing and
[52:11] Speaker 2: that I'm working on. I feel a little wobbly, I think,
[52:15] Speaker 2: because there are less buyers and there are less kind
[52:18] Speaker 2: of people to pitch to. And if it's a crazier idea,
[52:22] Speaker 2: you often hear like, let's hold on that for a
[52:24] Speaker 2: bit and then come back to it. So there's kind
[52:26] Speaker 2: of like that piece of it. Um, but the best
[52:29] Speaker 2: part of that work in progress is I've added starting
[52:33] Speaker 2: to do stand up the last few months and I'd
[52:36] Speaker 2: never done stand up before. It's insanely scary. So I'm
[52:41] Speaker 2: not on like the, it's a trajectory that just looks
[52:44] Speaker 2: like this. It's more of a, of a roller coaster
[52:47] Speaker 2: where I'm trying to get my sea legs on there
[52:50] Speaker 2: and see what's funny and what's not. And like, yeah,
[52:53] Speaker 2: does the R rated stuff. feel right or is my
[52:58] Speaker 2: thing the the nerdy political jokes like I really don't
[53:01] Speaker 2: know but finding that voice has been has been like
[53:03] Speaker 2: a really fun work in progress too.
[53:05] Speaker 1: Oh my god that's so exciting that's one of those
[53:07] Speaker 1: things that scares me so much but I I I
[53:10] Speaker 1: have like vulnerably for me I have like a little
[53:13] Speaker 1: pin and I'm like someday.
[53:14] Speaker 2: Yeah you should do it I don't know.
[53:19] Speaker 1: It feels terrifying yeah it's so exciting Well, I'm super
[53:23] Speaker 1: happy for you. Congratulations on all things.
[53:26] Speaker 2: Thank you.
[53:27] Speaker 1: This was such a pleasure.
[53:28] Speaker 2: This was awesome. It's great to see you again.

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