Why Kal Penn is Disillusioned with Democrats

Summary

Episode Overview

Podcast: Hasan Minhaj Doesn't Know
Host: Hasan Minhaj (presented by 186k Films)
Guest: Kal Penn
Episode Title: Why Kal Penn is Disillusioned with Democrats
Date: February 11, 2026

This episode features an insightful, candid, and often humorous conversation between Hasan Minhaj and actor/former White House staffer Kal Penn. Together, they dive into Penn's Hollywood and political careers, the hard truths about progressivism in the Democratic Party, and Kal’s mounting disillusionment with establishment politics—particularly around Gaza. The episode also touches on activism, Asian and South Asian representation, and advice for civic engagement, peppered with personal anecdotes and memorable stories from both screen and campaign trail.

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Key Discussion Points & Insights

Zoran Mamdani’s Election and Representation (04:05–07:00)

• Celebration of Zoran Mamdani’s Win: Kal recounts the electrifying atmosphere at Zoran Mamdani’s election night, sharing pride as someone who’s known Zoran since age 14.
  • Quote: “To just be standing there was so such an overwhelming feeling that I'm just like, proud of him, you know, even politics aside, you're, like, proud.” (Kal Penn, 04:47)
• Cultural Legacy: Both hosts reflect on seeing South Asian faces on screen and in politics, articulating the importance of representation.
• Advice to Zoran’s Supporters: Kal stresses collective political pressure for lasting change.
  • Quote: “He can't unilaterally, single handedly get a lot of this stuff done that he wants to get done, but he absolutely can get it done in partnership with this sea of people who came out to support him.” (Kal Penn, 03:27 and 39:00)

Breaking Barriers in Hollywood (07:00–09:30)

• Harold & Kumar’s Unlikely Impact: Kal describes skepticism about two Asian leads headlining a studio film and Hollywood’s underestimation of American audiences.
  • Quote: “...what you're doing by saying two Asian American men can't open a studio comedy is you're undermining a white audience. You're saying that white audiences are too racist and too stupid to enjoy just a buddy comedy. And I kind of rejected that.” (Kal Penn, 07:22)
• Growth in South Asian Creative Output: Both marvel at how diverse and nuanced South Asian stories have become in Hollywood.

Joining and Working in the Obama White House (09:32–16:18)

• Journey from Actor to Public Servant: Kal explains his accidental path from House MD to the Obama campaign and White House, combining steady acting gigs with political volunteering out of genuine conviction.
• Lessons in Political Gatekeeping: Kal’s naïve but honest approach to applying for a White House job—uploading a résumé through change.gov—leads to a funny Michelle Obama anecdote.
  • Quote: “She looked at me the way you look at somebody if they, like, drop an ice cream cone on the ground on gravel and then pick it up and eat it, like, what is wrong with you?” (Kal Penn, 13:18)
• Reflection on Political Access: Insight into how political “gatekeeping” prevents newcomers from breaking in.

Obama Era: Progress, Pitfalls, and Political Realpolitik (16:19–24:22)

• Has Obama Failed Us—or Moved the Needle?: Kal defends the notion that what’s progressive changes over time and lauds difficult legislative victories like “Don’t Ask, Don’t Tell”—while acknowledging the left’s (and his own) frustrations.
  • Quote: “Of course, by a 2025 lens, Obama was not a progressive. That's how, you know, progress worked. …because the needle was moved.” (Kal Penn, 02:04 and 16:28)
• Frustrations with Democratic Incrementalism: Details about the complex political calculus needed to pass the ACA and why Obama couldn’t always go further left.
• Disillusionment Within the White House: Kal admits to moments of internal protest, literal and figurative, met with nuanced rationales—democracy is slow, and direct action has limits.
  • Quote: “I printed out a photo of a backbone and I put it, stuck it to the wall. Like, people in this fucking building need one of these.” (Kal Penn, 22:54)

Gaza, Youth, and Disconnection from the Base (26:02–36:14)

• Calling Out the Biden Administration: Kal describes his process before going public: private advocacy, direct letters to officials (even to Blinken via aides), and eventual frustration when met with silence.
  • Quote: “It was just incredibly, deeply disturbing that there was no room for a conversation about anything.” (Kal Penn, 27:04)
• Activism and Engagement Shut Out: The episode recounts moments when young activists—especially the College Democrats—couldn’t even get meetings with national leaders:
  • Quote: “They said, we didn't have any conversations with them. They wouldn't even reach back out to us to have a meeting. ... Biden and Harris refused to even meet with the College Democrats of America.” (Kal Penn, 34:00)
• Lessons from the DNC in Chicago: Both reflect on protest exclusion tactics and the illusion of participatory democracy.

Civic Participation and Political Change (36:14–39:37)

• How to Actually Move the Needle (Locally): Kal offers prescriptive advice for civic engagement in the city, emphasizing the necessity of organized pressure and building coalitions.
  • Quote: “The best way to meet this moment… is actually using the political capital that Zoran earned by getting people out to vote for him and… turning that into real political action.” (Kal Penn, 36:32)

Navigating Compromise as a Minority in Entertainment (46:42–56:36)

• Racism and Exclusion in Early Hollywood: Kal recounts working for “Captain Moneybags,” a brazenly racist producer, and witnessing how hard it was for Asian actors to get breaks.
  • Quote: “I'm not trying to cast fucking Asians in my movie. Cal, bring me good white American actors.” (Captain Moneybags, paraphrased by Kal Penn, 43:29)
• Dealing with Stereotypes and the Need for Strategic Compromise: Kal shares the infamous Van Wilder audition—with white actors literally donning brownface as competitors—and his subsequent embrace of strategic compromise.
  • Quote: “It's one thing to, like, oh, you put a screen name… but what this guy was showing me was that that didn't even matter. …You're illustrating to me that the standard way of doing things isn't going to work. …So I have two choices. I can be a bitch and lament and whine about how this isn't going to work out, or I can strategize about a different way in.” (Kal Penn, 46:02 & 46:42)
• Calculating When to Say Yes (and Influence From Within): Advice from a casting executive leads to Kal demanding script changes (and making the role funnier), ultimately opening doors for more meaningful representation in later projects like Harold & Kumar and The Namesake.

The Value of Kindness and Collaboration in Hollywood (47:01–48:21)

• Why Are People in Hollywood Jerks?: Kal argues that most “asshole-ishness” stems from insecurity; “kindness brings out everybody’s artistic vision.”

Full-Circle Moments in Representation (55:55–56:36)

• Networking and Persistence: Kal’s path from Van Wilder to Harold & Kumar to The Namesake is directly shaped by earlier compromises and a network built through honest hustle.
• Art Inspiring Art: The arc comes full circle through Mira Nair, who gives Kal a shot because of her son’s admiration for Harold & Kumar.

On Podcasting and New Projects (56:36–58:53)

• Kal’s New Podcasts: “Here We Go Again” explores political and cultural cycles with wit; his other show is a literary book club co-hosted with Ed Helms.

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Notable Quotes & Memorable Moments

• On Progress:
  “Of course, by a 2025 lens, Obama was not a progressive. That's how you know progress worked because the needle was moved.”
  —Kal Penn (02:04, repeated and unpacked at 16:28)

• On Political Establishment:
  “There was no room for a conversation about anything.”
  —Kal Penn (27:04)

• On Civic Engagement:
  “The best way to meet this moment… is actually using the political capital that Zoran earned by getting people out to vote for him and… turning that into real political action.”
  —Kal Penn (36:32)

• On Strategic Compromise:
  “I can be a bitch and lament and whine about how this isn't going to work out, or I can strategize about a different way in.”
  —Kal Penn (46:42)

• On Representation and Inspiration:
  “If this woman, Mira Nair, can do this, then like maybe I can too.”
  —Kal Penn (40:44, on seeing Mississippi Masala)

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Segment Timestamps

| Timestamp | Summary | |------------|--------------------------------------------------------| | 04:05–07:00| Zoran Mamdani’s win; importance of representation | | 07:00–09:30| Asian representation in film; Harold & Kumar’s journey | | 09:32–16:18| Obama campaign and White House, lessons learned | | 16:19–24:22| Obama’s progressivism, policy tradeoffs, disillusionment| | 26:02–36:14| Gaza, youth activism, disconnection from Biden Dems | | 36:14–39:37| How citizens & activists can turn movements to action | | 46:42–56:36| Racism in Hollywood, compromise vs. principle | | 56:36–58:53| Kal’s new podcasts; continuing the conversation |

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Tone & Language

• Conversational, irreverent, but deeply sincere and honest
• Mix of storytelling, personal confession, and social critique
• Balances comedy (“If I’m lying, I’m dying!”) and seriousness (“...no room for a conversation about anything.”)
• Encourages critical reflection, community action, and empathy without preachiness

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Takeaways for New Listeners

• This episode is part masterclass in negotiating systemic adversity and part roadmap for activism within seemingly unresponsive institutions.
• Kal Penn’s arc is one of persistent optimism, tempered realism, and hard-won insight—on both the difficulty and necessity of working within flawed systems, whether in Washington or Hollywood.
• The conversation leaves listeners with a call to action: engagement, coalition-building, and finding ways to move the needle—no matter how steep the odds.

Transcript

[Aziz Ansari]

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[Kal Penn]

Lemonade of course by a 2025 lens, Obama was not a progressive. That's how you know progress worked because the needle was moved.

[Aziz Ansari]

Kal Penn is a legend. He took a cringy character named Taj Mahal Bharalan and made it to be as good as it could possibly be, and leveraged that role to star in one of the best stoner comedies of all time, while also inspiring me and so many other young brown kids around the world to do comedy. But that was just the start of an incredible career that took him from a leading role in major studio films to major network dramas, to the Obama White House, and then back to acting, where he is playing a White House press secretary. And now to his latest project, a new podcast called Here We Go Again. So I sat down with one of my comedy heroes to talk about some of his craziest stories coming up in Hollywood.

[Kal Penn]

I hand him Joseph Gordon Levitt's headshot. And he gets to Joseph's headshot and goes, what the. Is this kid Asian?

[Aziz Ansari]

And we got into his time in the Obama administration in his disillusionment with Biden and the Democrats over Gaza, and.

[Kal Penn]

It was just incredibly, deeply disturbing that it. That there was no room for a conversation.

[Aziz Ansari]

We also talked about his long friendship with Zoran Mamdani.

[Kal Penn]

You have no Zoron since he was 14. So just so proud of him and.

[Aziz Ansari]

His advice to Zoron supporters.

[Kal Penn]

He can't unilaterally, single handedly get a lot of this stuff done that he wants to get done, but he absolutely can get it done in partnership with this sea of people who came out to support him.

[Aziz Ansari]

And he didn't come on here to promote his memoir. You can't be serious. But I will promote it anyway because it's a guidebook on how to succeed in Hollywood without being an asshole. Yes, it's possible. Unless your name is Ronny Chieng.

[Kal Penn]

Hurry right away, no delay. Make your daddy glad. You have had such a.

[Aziz Ansari]

So the last time we saw each other, we were at Zoron's election night.

[Kal Penn]

Party two weeks ago, right? Two weeks ago, yeah.

[Aziz Ansari]

Two weeks ago.

[Kal Penn]

Yeah.

[Aziz Ansari]

Legendary night. Momentous night.

[Kal Penn]

Yes.

[Aziz Ansari]

Two questions. Number one, how did it feel for you that night?

[Kal Penn]

Oh, man. So I'll tell you. I mean, it felt incredible. Right. And for folks who don't know, I've known Zoran since he was 14. There's a whole backstory there. But we found out that he won when we were standing in line on the way in.

[Aziz Ansari]

Yes.

[Kal Penn]

And I worked on a film called the Namesake written by Jhumpa Lahiri. The. The novel's written by J. Lahiri Mira Zoran's mom directed the film.

[Aziz Ansari]

Yeah.

[Kal Penn]

And it's my favorite thing I've ever done. And I'm standing with my partner, Josh With Jumpa, her husband, her son, they all.

[Aziz Ansari]

Oh, Ja was there.

[Kal Penn]

Yeah, yeah, yeah. Jumpa was there.

[Aziz Ansari]

So Jumpa is the author of the.

[Kal Penn]

The novel, the critical.

[Aziz Ansari]

Huge, you know, massive hit, Pulitzer winner.

[Kal Penn]

Like, so I'm standing with her on one side and then Motaz, the photojournalist from Gaza. Yeah. On the other side. Yes. And we all find out that he won. And it was just such an insane moment because it's, you know, somebody who I know intimately, whose work I admire, who I worked with. Yeah. And then on the other side, somebody who's just such an icon for human rights right now. And to just be standing there was so such an overwhelming feeling that I'm just like, proud of him, you know, even politics aside, you're, like, proud.

[Aziz Ansari]

Yeah. It was a surreal moment. I couldn't believe it was happening. And it also was happening on a very, like, historic day. Dick Cheney dies. He wins. No, because usually the news is always like, yeah, yeah, white man wins.

[Kal Penn]

Right.

[Aziz Ansari]

Brown boy dies.

[Kal Penn]

Right.

[Aziz Ansari]

This was like the opposite, which is like, brown boys up. Yeah, white man dies. I was like, this is like whole flipping of the.

[Kal Penn]

It was a spider verse, generational sort of shift, maybe.

[Aziz Ansari]

Yeah, right.

[Kal Penn]

Like, it was something. It was something.

[Aziz Ansari]

So you were there. I was there. Asif Manvi was there and Rami was there.

[Kal Penn]

Yeah.

[Aziz Ansari]

And then I pulled you and Rami to the side and I was like, you two are New Jersey legends.

[Kal Penn]

That's right.

[Aziz Ansari]

And then what was so interesting was I thought it was really beautiful that me and Rami gave you your flowers.

[Kal Penn]

That was insane. I couldn't believe that that was happening because I admire.

[Aziz Ansari]

Why? Why was it so unbelievable?

[Kal Penn]

Because I admire you guys very much. You gave me the type of flowers that, you know, like, you're, both of you at this, like, I hate to say peak because it should just continue to go up, but at the peak of comedy career, at the peak of like. And neither of you just tell jokes, you guys also, like, the soul of something meaningful and biting and a reflection of society, always led with joy is such a rare trait that, like, I. I mean, I told you this that night. I've just started dabbling with stand up comedy. Right, Right. It's finding my voice. It'll take years to figure that out. But that the, the ability to craft all of that and to lead with joy is something I admire so much. So to hear both of you guys.

[Aziz Ansari]

I'm not good at accepting compliments.

[Kal Penn]

I'm telling you, to hear both of you guys say this to me and Give me those flowers that night, bro.

[Aziz Ansari]

You think I'm lying? You fact check this, bro.

[Kal Penn]

Look.

[Aziz Ansari]

Look at the set. Oh, this is seminal. These are all the things that made me.

[Kal Penn]

Oh, man.

[Aziz Ansari]

Bro, you think if I'm lying, I'm dying.

[Kal Penn]

Oh, wow.

[Aziz Ansari]

Story that I told that night was for both me and Rami. I was in college at the time. He was in high school at the time. So to go to a Cineplex in 2004 and to see this as the poster.

[Kal Penn]

Well, thank you. I mean, that. That movie really launched my career.

[Aziz Ansari]

Right.

[Kal Penn]

And I will say you're right. So nobody saw it in the box office. It really underperformed.

[Aziz Ansari]

Yeah.

[Kal Penn]

And. And. And back then, like, to your point about the poster, right, there were people in Hollywood who were like, we don't know, can two Asian American men open a studio comedy? And the general consensus was no. Right. Because it hadn't been done before. And we always thought, like, well, the script is so funny. I. I think what you're doing by saying two Asian American men can't. Can't open a studio comedy is you're undermining a white audience. You're saying that white audiences are too racist and too stupid to enjoy just a buddy comedy. And I kind of rejected that. Then the movie comes out, and it totally tanks in the box office the first two weeks. And for the next six months, like, I'm not getting any auditions. Really? Yeah, yeah, dude. Because your movie failed.

[Aziz Ansari]

Oh, interesting.

[Kal Penn]

And then it kind of softly gets launched on dvd. Zero marketing budget. It ends up on hbo, and within a month, like, you can't walk down the street without people being like, dude, that movie is so funny. That movie so funny. So when you hear me, John Cho, like, the writers talk with reverence about. About our love for the fans, it is truly because this movie wasn't supposed to take off. The fans found it on their own. They bought the dvd. They had watch parties in their dorm rooms, like, and by the way, all over the country. Nebraska, Illinois, Alabama. It wasn't just the coast, you know. Yeah. And so it felt. It felt validating to know that, like, yeah, we were right. Audiences just want to laugh.

[Aziz Ansari]

Is it incredible for you to see how far South Asian and diaspora cinema has gone since those moments in Those early editions?

[Kal Penn]

100%. It's incredible to see just the. The breadth of talent that's out there, the diversity and. And not just on camera, not just racial or ethnic diversity, but, like, the. The diversity of stories that are being told. So there's such a. A Difference between, like, I don't know, like a. Like any of the stuff that Mindy writes. Incredible. Really funny. Compared to like the. The grit of like a Super Troopers or the grit of like your movie that's coming out. Right. Like they couldn't be more different. Very different.

[Aziz Ansari]

Yeah.

[Kal Penn]

It's. It's so exciting. Also, there's so many executives now, people in the finance world who are looking for stories that are just interesting, period. Lily's movie that just came out. Doing it.

[Aziz Ansari]

Yeah.

[Kal Penn]

Really funny.

[Aziz Ansari]

Yeah.

[Julia Louis-Dreyfus]

Yeah.

[Kal Penn]

Feels good to see that.

[Aziz Ansari]

I kind of want to walk people through your reasoning as to why you joined the Obama White House in 070809. Where the country was at that time and where you were at that time. Because you were on House.

[Kal Penn]

I was.

[Aziz Ansari]

And then you decide to say, goodbye, Hollywood.

[Kal Penn]

Yeah. Goodbye.

[Aziz Ansari]

Goodbye healthcare. Goodbye, air conditioned trailer.

[Kal Penn]

Yeah. Yeah.

[Aziz Ansari]

I'm moving to dc.

[Kal Penn]

Yeah. So I had no intention of working in public service. Very happy to be working on house. Regular paycheck.

[Aziz Ansari]

Yeah.

[Kal Penn]

Parking spot with my name on it.

[Aziz Ansari]

Fucking amazing trailer. Incredible.

[Kal Penn]

Playing a doctor. Little response on the family side.

[Aziz Ansari]

No accent.

[Kal Penn]

No accent.

[Aziz Ansari]

All star cast. You a little. Incredible cast.

[Kal Penn]

Hugh Laurie. Hugh Laurie.

[Aziz Ansari]

I mean, great cast. Yeah.

[Kal Penn]

And in 2000, October 2007, Olivia knocks on my trailer door and she's like, hey, I have a plus one to a Barack Obama campaign event. Do you want to come? And I was like, no, I'm good. She goes, but I saw you reading his book. And I was like, yeah, I also read a book about Dick Cheney. Don't need to meet Dick Cheney. You know, I just. I like to read. And she basically this got to the point where she's like, it's an open bar. And I'm like, sweet. I'm down. So I'm like, all right, all these artists are going to ask great questions about, like, public arts funding and free speech and stuff like that. So I want to ask, like a smarter question.

[Aziz Ansari]

Okay.

[Kal Penn]

I want to ask a question out of left field. I'm going to ask a question about climate change. I remember this foreign affairs article. I have like nine glasses of wine, which was a mistake. And then we meet Obama. Yeah. And I was like, sir, I have a. I have a question for you. You know, I was reading your website and I saw that you want to invest in corn for ethanol. That's just going to drive the price of corn up in developing countries. And Obama gives me this, like, the look that everybody now knows is like, cocky Obama look. Right? And he goes, well, if you read My. My website, carefully. You would have seen that I'm investing in corn based ethanol as a bridge to cellulosic ethanol so that we can make biofuels from raking the leaves in your yard and grass clippings when you mow the lawn. And then he gave me another smirk and he sort of walked off. And Olivia was just like, yo, you just got schooled by Barack Obama. We both signed up to volunteer for his campaign that evening. Because I'm like, all right, I can do an event for him and then jump ahead, like, you know, 12, 12, 15 months. So campaign ends. I've been working on it for more than a year while acting. And you get this email if you worked on the campaign, that said, if you'd like to be considered for a White House job or anything in the administration, there's a website called change.gov that has been set up. Upload your CV, your resume, a little cover letter.

[Aziz Ansari]

Yeah.

[Kal Penn]

And somebody will call you if you're the right fit. So I did this. I didn't tell anybody except my manager at the time, my acting manager. And he was like, that's crazy. Why would you do that? Will you go work at the White House? And I was like, I doubt I'm qualified, but if I am, like, yeah, I think it'd be interesting to take a year off and serve. So he's like, all right, whatever. So months go by. This was in November, a couple months go by in January. I'm in D.C. for the inauguration. And you get to bring some people with you. My parents, my brother, my manager. And backstage, you get to say hi to the incoming first family. So Obama comes through, hey, thanks for everything. You know, all very cordial. Mrs. Obama comes through, like, 10 minutes later, and I hadn't met her before, and she's like, cal, thank you so much for, like, volunteering for the last year, year and a half. I hope you stay involved. And I was like, yeah, me too. I would love to. Thinking, like, that's just something Michelle Obama says to everybody. My manager, who's standing next to me and was basically like every character from the HBO show Entourage in one person, okay. Says to Michelle Obama, well, you know, he applied for a job, right? And I'm like, oh, no, no, no. This is not.

[Aziz Ansari]

Totally not the first lady.

[Kal Penn]

She's like, what do you mean? Yeah, he applied for a job and nobody even called him back. And she looks at me and she's like, who did you apply with?

[Aziz Ansari]

I went to the website, like, I.

[Kal Penn]

Didn'T want to bother Anybody. So I uploaded my CV to the website and she looked at me the way you look at somebody if they, like, drop an ice cream cone on the ground on gravel and then pick it up and eat it, like, what is wrong with you? Kind of thing, right? And she calls the president over and goes, tell him. Tell him what you just told me. I was like, well, sir, I applied for a job at the White House. Oh, who'd you apply with? And I was like, I uploaded my CV to change.gov, and he was, like, a little amused, but he was basically like, are you serious? Is this really something you want to do? And somebody on his team reached out and said, actually, incidentally, we're looking. We only have the salary to pay for one White House staffer, but we need that person to cover youth outreach and engagement, Asian American outreach and engagement and arts arts outreach, and I arts in general outreach to the arts community. And I had done all three of those in, in the campaign. And I also, I just finished up teaching a semester at UPenn in Asian American Studies. So it was like, the timing was kind of perfect, right? But the end of that, I was obviously deeply embarrassed. The real takeaway, for me, as actors, you're so used to having to go through your gatekeepers, your, Your manager, your, Your team, whatever, that I thought I was doing the right thing by just putting my resume out and, like, if I'm qualified, it'll rise to the top. So what it looked like to them was, he's not serious. Because if he was, if you worked for a startup at its infancy for a year, and then the startup got bought out twice, and you have the chance to work for that new company where your boss is in the leadership role, are you just going to upload your resume or you're going to call your boss and be like, hey, man, I would love to help you execute on all these promises. That was a big lesson learned for me. It sounds stupid in retrospect. Like, how dumb are you that you just uploaded your cv? So, you know, props to that.

[Aziz Ansari]

Well, also, like, we don't come from a culture of Legacy admission.

[Kal Penn]

Oh, 100%.

[Aziz Ansari]

Yeah, of course. I'm going to go to website.combackslash apply.

[Kal Penn]

Yeah, the I don't want to bother you backslash.

[Aziz Ansari]

That's the point. But the lesson here is that they don't fucking check that thing. And did they know or did they know? They're like, no, no, we didn't.

[Kal Penn]

They didn't know. They didn't. I mean, it's sort of like, like Xeron's website now. 50,000 applications to work in New York City government. Amazing. You know, but I doubt that just uploading your resume is gonna.

[Aziz Ansari]

Damn.

[Kal Penn]

Yeah.

[Aziz Ansari]

There's so many people that uploaded the resume to that then.

[Kal Penn]

Yeah, for sure. Yeah.

[Aziz Ansari]

When we talk about discourse around the Obama presidency, there's people that were like, he was a great president.

[Kal Penn]

Yeah.

[Aziz Ansari]

There's people that are like, thanks, Obama, you didn't do anything for us.

[Kal Penn]

Yeah.

[Aziz Ansari]

As someone who worked in 1600 Pennsylvania Avenue.

[Kal Penn]

Yeah.

[Aziz Ansari]

Call balls and strikes. How was the Obama presidency and how did it shape your view of the presidency?

[Kal Penn]

I'll say this in answering the question. Yeah, I hear all of that.

[Aziz Ansari]

There's no gotcha.

[Kal Penn]

No, no, there's no gotcha.

[Aziz Ansari]

It's, it's. It of a. You walked the walk.

[Kal Penn]

Yeah, yeah.

[Aziz Ansari]

It's the same way I feel about when people outside of whatever my domain of expertise is, which is very small, let's say stand up comedy.

[Kal Penn]

Well, but you have your ear to.

[Aziz Ansari]

The ground in theaters or whatever, whatever that stupid thing is, or, you know, the Ticketmaster experience for buying comedy tickets. That's my. But I say that to say is, yeah, hey, I know this deeply.

[Kal Penn]

Yeah.

[Aziz Ansari]

And I can talk to you about it deeply. You have the ability to do that outside of the op ed page.

[Kal Penn]

Yeah, yeah.

[Aziz Ansari]

Just firing off page A8.

[Kal Penn]

I think. I think what is what will never cease to be fascinating to me. 2025 right now, right?

[Aziz Ansari]

Yeah.

[Kal Penn]

The Obama years I was there was 2009 to 2011. You can't look back at 2009 with a 2025 lens and say this wasn't progressive enough. And I will tell you why is that. Of course, by a 2025 lens, Obama was not a progressive. That's how, you know, progress worked. It's a good thing. It's a good luxury to be able to look back and be like that moderate, that dude who droned people and didn't get healthcare passed the way that we wanted. That's a great ability to have in 2025 because it means that things that he did get done are moderate by definition. Today because the needle was moved. There were obviously plenty of things I disagreed with that the administration did. Plenty of things I think he did right. That maybe he didn't get credit for. I think the big lesson looking was seeing how like, you know, I haven't talked to the president about this, but the perspective I have of like the years I was there, everything was, let's get it done legislatively. Let's not do executive orders. Let's not just unilaterally try to make something happen. Let's get the buy in. And I remember don't ask, don't tell. For example, there were a lot of advocates on the left who rightfully were like, we don't want to wait for Congress to pass something. Sign an executive order right now. That gets rid of don't ask, don't tell, which is something he could have done. The reason he didn't want to do that is any future president could easily sign an executive order bringing back don't ask, don't tell. It's really hard if you do it with Congress because you have to get 60 votes in the Senate, however many, and then have a president sign. So it's almost.

[Aziz Ansari]

There's more levers that have to be pulled.

[Kal Penn]

It's very difficult to overturn something legislative. And so like, those advocates were obviously livid. We had people chaining themselves to the White House gates saying, Obama doesn't care about gay folks and you need to sign an executive order. Now, in retrospect, using the 2025 lens, right. We would have had don't ask, don't tell back in effect today, easy if it wasn't legislatively done. So I think having the patience to look back and take those lessons from it, I find really interesting. Which is a little bit different than, look, we live in a world where people want change to be like a light switch. And democracy is designed to move slowly. So I think those lessons are important and, and interesting. For sure. People have a right to be disappointed. People have a right to celebrate.

[Aziz Ansari]

I mean, what I'd love your insight on, actually is what's really interesting that you're saying here is, is there a case for establishment progressivism or should Barack Obama have been more wildly radical?

[Kal Penn]

The problem with this question is that the reality was he couldn't be wildly radical. Right. So even the Affordable Care act at the time, even though the initial point of it was actually like a conservative model, but even then he barely got the Democratic votes to get it passed. And in retrospect, we're like, that's all we got. So, like, it's. Of course, I wish people had a magic wand. I wish everybody could have been more lefty and more progressive. But if you're looking at what a president can and can't do, you also have to look at, like, the political capital around it.

[Aziz Ansari]

Yeah.

[Kal Penn]

And there were the way that the voter trading works. Right. Again, I haven't had conversations with the President about this. But for example, I remember hearing he ran this campaign on, if I'm elected, I'm not going to trade favors. I'm not going to do a fundraiser for you in exchange for you vote yes. I remember I was hearing stories that there were members of Congress who would call and be like, hey, we need an invitation to play golf with the president so I can get a photo for my newsletter and in exchange will vote yes on the Affordable Care Act. And the White House was like, you should vote yes on the Affordable Care Act. If you think your constituents need health.

[Aziz Ansari]

Care, do the newsletter.

[Kal Penn]

This is the right path. But that's what I'm saying is if you're the, if you're the guy who ran on not doing the newsletter, right. And saying, this is how we're going to change the nature of politics, I think looking back and saying, should something have been different? It's also important to like, you know, take all of that into account. I think in a one photo on.

[Aziz Ansari]

An iPhone 6 in exchange for.

[Kal Penn]

In exchange for a no. But then you got to deal with that person for three hours in a golf round.

[Aziz Ansari]

You know, you can hit unsubscribe on the Yahoo. Email listserv.

[Kal Penn]

Can I give you one example?

[Aziz Ansari]

Sure.

[Kal Penn]

Something that I think about a lot, right. I'm. I'm way farther left of the establishment on things like national security, on military, industrial complex, all of that. And I would never make an excuse for it because I think it's wrong. The, the types of things I find interesting are things like, so Obama pledges to close Guantanamo. Right. And one of the ways to do that is by making sure that Congress transfers detainees. Congress almost unilaterally, like, rejected Dems and Republicans rejected this because nobody wanted detainees in their own states. Yeah. So it's a. Obviously the conversation's longer than that, but. So Obama fails, but the argument is.

[Aziz Ansari]

I'm not going to just harbor a terrorist.

[Kal Penn]

And I go, so Obama fails their reasoning at closing Guantanamo, which obviously is disappointing. But it's things like that that I look at where. And I especially think about this when it comes to like presidential elections, mayoral elections, and any kind of leadership thing where we, we put everything in one bucket, but it's easier to target one person than it is for the full field. So anything that requires legislative action, we obviously don't live in that world necessarily now in a Trump administration, but like holding Democratic members accountable, like the boring ass person who represents you in Congress who could use like maybe a protest in front of their office every now and then, like, that stuff is actually really important to get them to fall in line for something that somebody wants to do. But I. I cut you off. I cut you off.

[Aziz Ansari]

No, no, no. I think. Was there a particular moment that you became disillusioned with it all? Was it perhaps the Merrick Garland decision? Were there moments where you were like, hey, playing nice doesn't work? Or do you feel like, no, this was the right move for that eight year window?

[Kal Penn]

That period of time, I was only there for the two. Right. I. I was. There were plenty of times I was disillusioned, dude. There was a. There was a day probably like a month and a half into me being in the White House. Shared an office with like six other people. I can't remember what the decision was, but there was something the White House was doing that I thought was like, there's just no backbone. Here's the. Here's what happens when a dramatic, like a drama queen actor is in the White House.

[Aziz Ansari]

You did a monologue.

[Kal Penn]

I print. I almost did a monologue. I printed out a photo of a backbone and I put it, stuck it to the wall. Like, people in this fucking building need one of these. Right. And then I went off on a rant.

[Aziz Ansari]

Evisceration.

[Kal Penn]

Yeah. And one of my co workers was like, let's go for a walk. And she schools me on the strategy behind what I thought was not having a backbone now. It didn't change my mind. I was still frustrated. So there are plenty of moments like that, and there are plenty of moments that were like an example of something I thought that we did. Right. Opening up relations with Cuba. Right. So my friend Ben Rhodes, who now hosts POD Save the World, he was in charge of negotiating secretly with the Cubans on, like, the Major League Baseball deal and cultural diplomacy and things like that. This was after I had left the White House, but I was working on an arts policy committee at the time. So we did the first ever cultural delegation to Havana after this. I thought that was the right decision. The way of engaging with Cuba since the embargo started hadn't worked. Not everybody agreed with that. Obviously, both Trump and Biden rescinded all of this and sort of kept it locked. I think Biden opened it up like a day before he left office or whatever. But. So those are. Those are choices that the President took a lot of heat for that I thought he did. Right. There were plenty of things that I was just really disillusioned and bummed out about. You know, I didn't Mean, to joke about the drone stuff, but foreign policy, unilateral stuff against Palestinians. Again, you know, there's all of that. That. I just think that's the Democratic Party line. That's a real bummer.

[Aziz Ansari]

So I have a bit in my previous special where I basically say, being a fan of a president is like being a fan of a national bank.

[Kal Penn]

Yeah.

[Aziz Ansari]

Like walking around, you know, Wells Fargo.

[Kal Penn]

Yeah, yeah, yeah, yeah, yeah.

[Aziz Ansari]

And I'm like, they're going to disappoint you for different reasons, but they will disappoint you. But I'm just being a comedian throwing spitballs from the back of the class.

[Kal Penn]

Yeah.

[Aziz Ansari]

You've actually really engaged with the process. What is a healthy relationship that one should have with the presidency? Meaning someone who is a voting citizen, someone who is a volunteer, and maybe someone who bought the T shirt. Sadly.

[Kal Penn]

Yeah. The T shirt of the band. I think a healthy relationship is like understanding from the beginning that you're. You should not agree with 100 of what this person is saying or doing. Like, if you do, that's insanity. That's just. Then you get into sycophantic stuff. And there's plenty of sycophant. There was plenty of sycophantic stuff around Obama at the time. There's so much sycophantic stuff around Zoran, for example. And I think the healthy thing to do is be like, I don't agree with everything this person is doing.

[Aziz Ansari]

Right.

[Kal Penn]

But is the net part of that something that. I feel like this is a step forward. And in any healthy democracy, the fact that people disagree means you're never going to get 100% of what you want. So are you going to burn it all down because you're not getting everything you want, or are you going to be okay with getting 20% of what you want, 40% of what you want, and view that as a victory that you have to build on. And I know it sounds like fucking Cook talking points, but really, like, that's how healthy democracy works.

[Aziz Ansari]

When it came to the issue with Gaza, you went out and you condemned the administration.

[Kal Penn]

Yeah.

[Aziz Ansari]

And that's. That must have been tough for you. You know, a lot of people that work in the administration, these are friends, colleagues, people that have your cell phone number.

[Kal Penn]

Yeah.

[Aziz Ansari]

So it's not just like a dunk on a Instagram post or whatever you are. Some of that political capital that you have built and the friendships that you've built, you've. You're calling those people out. How did you navigate that?

[Kal Penn]

That was one of the most disappointing and frankly, naively now, in retrospect, surprising things. I remember thinking to myself, and there were a group of us that would text about this. And I remember, like Ben Rhodes, for example, who's been very outspoken, you know, chatting with him, chatting with other people who worked in the National Security Council, in the Obama White House, who are more aligned with what, like a Rhodes or I believe, in our view, kind of thought. Okay, before I, like go out there and tweet about something, I have these relationships, like, let me, let me call them. Let me send a note to, like, Blinken and Kamala, like, this is. The whole point of having these relationships is, hey, I'm really.

[Aziz Ansari]

You had Anthony Blinken's email.

[Kal Penn]

I sent. I sent it to an aide. Yeah.

[Aziz Ansari]

Wow.

[Kal Penn]

And made sure he saw it. Like, yes, the secretary's seen this. I'm like, great. And these are, these are letters that just not as an actor. Not that there's no shade to that, but like, primarily as, hey, I was Obama's youth guy. Here's what I'm hearing. Biden never had a youth liaison in the public engagement office. So I'm like, you guys don't have one. I was the last. Sorry, that's not true. Because there were others after I left the White House, but our administration was the last successful youth outreach administration or at least somebody who had that job. So I'm putting all of that out there. And I had phone calls with some of these people and it was just incredibly, deeply disturbing that it. That there was no room for a conversation about anything. And so the national security cultural diplomacy stuff that I do is mostly rooted in human rights and cultural diplomacy within human rights. So it was just a real bummer, frankly. But I thought that before I. So what you're probably referring to are some of the tweets or posts that I made are fundraisers for Doctors Without Borders and what the hell are we doing here? But the starting point for that, for a good six to eight months, was still believing that that private pressure would work. And obviously, you know, it didn't, which is a bummer.

[Aziz Ansari]

This episode of HMDK is brought to you by Booking.com I love to travel, but I can't say that it's easy. My family has never been described as low maintenance. We all have different ideas of relaxing. What is fun for my 70 year old parents is the opposite of what is fun for my younger cousins. Thankfully, booking.com offers a wide array of hotels and vacation rentals across the United States. So There is something for everyone, even those who are impossible to please. I'm talking about you dad. Whether you're booking for yourself or your picky parents or da boys group chat, you can find exactly what you are booking for. For example, my number one request at a hotel or a rental is a sauna. Now I will settle for a steam room, but I gotta sweat out my demons. Speaking of, my kids appreciate a touch of whimsy. A cute window seat to read on, a water slide in the pool. A massive pile of construction dirt next door. They're not picky. Dare I say if we can find our Perfect stay on booking.com, anyone can find exactly what you are booking [e-mail] booking yeah, book today on the site or in the app. Valentine's Day has become quite the racket. Ladies and gentlemen. I want to celebrate with my boo. But I don't want a mandatory eight course tasting menu. Especially as someone with dietary restrictions. I'm looking at you, pork and alcohol. That is why I am making Bina dinner this year for Valentine's Day and it's never been easier. Now that I can use Whole Foods as my one stop shop. Whole Foods has anything you could possibly want for a romantic meal. Fresh herbs, sustainably wild, caught or responsibly farmed seafood, and antibiotic free steaks. Because nothing is more romantic than antibiotic free steaks. And don't skip dessert. This is arguably the whole point of the entire holiday. They've got heart shaped cakes and my favorite chocolate covered strawberries. Plus I can get my girl a bouquet of flowers. They even have arrangements in vases already. Are you hearing this? They're in vases. I don't have to arrange the flowers or go to multiple stores. It's the perfect way for us busy professionals to be thoughtful. Or for lazy people to seem thoughtful. Taste the love all month at Whole Foods Market and Happy Valentine's Day.

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Hiya Julia. Louis Dreyfus here from the Wiser Than Me podcast. Among other things. And I've got a bit of a hot take. Our relationship to our food can feel disconnected. We don't always know how or where our food is grown. And if we throw food scraps in the garbage, we don't think about where it's going. Or at least we try not to. One way that I get back a little of that connection is by using my Mill food recycler. Sure, Mill has totally changed my home life in a lot of practical ways. It works automatically. You can fill it for weeks. It never Ever smells. But this is also really important. When I use mill, I'm participating in a circular system. All the food I don't eat is helping to grow the food that I do. It makes me feel like I'm part of something big, bigger. And that feels really, really good. And it's all so ridiculously easy. I just drop my scraps in my mill and it transforms them into nutrient rich grounds overnight. I have mine sent to a small farm, but if I wanted to, I could use them in my garden or for my backyard chickens if I wanted backyard chickens. And I don't know, maybe I do now, maybe I don't. Anyway, maybe mill is transforming me too, just a little. If you want to feel more connected or you just want your kitchen to feel less gross, try Mill's risk free trial and just live with it for a while. Go to mill.com wiser for an exclusive offer.

[Kal Penn]

What?

[Aziz Ansari]

Now that you know that.

[Kal Penn]

Yeah.

[Aziz Ansari]

What do you do with that information?

[Kal Penn]

I think like a lot of people, I. I don't know who you support nationally with the Dems right now, I think we'll have to see what they mean by that. Decide to do meaning. I'm not a single issue voter, but in the next presidential election, people are gonna have to be held accountable about how do they feel about the universality of human rights.

[Aziz Ansari]

I just know a lot of people that were at the DNC in Chicago that were part of this movement called Undecided Voters.

[Kal Penn]

Yes.

[Aziz Ansari]

And they were protesting the war.

[Kal Penn]

Yeah.

[Aziz Ansari]

And the United States involvement in the war.

[Kal Penn]

Yes.

[Aziz Ansari]

And the way the city planning was is that you had the United center and they were sent miles away.

[Kal Penn]

Yeah.

[Aziz Ansari]

And I remember as a young kid being at the mosque and having local congressmen. You know, my dad tried to plug the community in any which way and some sort of civic activism. And he said, I remember he's now passed away as a congressman named Vic Fazio. And he was like, you know, the problem with you people is. And I was like, I'm a little offended by the fact that you call us you people. But he's like, you guys don't get involved. The moment you get involved, we as your representatives will have to hear you.

[Kal Penn]

Yeah.

[Aziz Ansari]

And I saw just all these people protesting in the park. These are people that you. You send your kids to high school with that go to fucking DePaul University. We're talking about pre med majors. These are just like regular people.

[Kal Penn]

Yeah, yeah.

[Aziz Ansari]

Not this kind of stuff that gets hijacked by the discourse.

[Kal Penn]

Yep.

[Aziz Ansari]

Just normal, everyday Americans Protesting this war. And they were sent miles away from the dnc. You couldn't hear him.

[Kal Penn]

Yeah.

[Aziz Ansari]

That signaled to me. I don't want to hear it.

[Kal Penn]

Correct.

[Aziz Ansari]

I don't want to hear you.

[Kal Penn]

Yes.

[Aziz Ansari]

I don't want to see what you have to say.

[Kal Penn]

Right.

[Aziz Ansari]

And I'm not going to create a path for you to even communicate with us.

[Kal Penn]

That's right.

[Aziz Ansari]

It was, you know, 96 straight hours of people talking at the DNC. We're not going to give you a slot to speak. So.

[Kal Penn]

Not even one slot.

[Aziz Ansari]

Yeah. So. So for me, again, as like a comedian, satirist, all that sort of stuff, I can't. I can't tell people what they should do with their vote.

[Kal Penn]

Yeah.

[Aziz Ansari]

Because I witness with my own eyes people that were trying to engage.

[Kal Penn]

Yeah. I help out the college Dems. I'm on their advisory board. And at some point, I can't remember the month, but I saw that they wrote this op ed that was very critical of Harris and Biden in the Washington Post around Gaza and around Youth Vote and Gaza. And I called them and I was like, hey, I'm super curious about what the meetings were like with the White House that led you to the place where you, as college Dems in their own party, felt the need to publicly write that letter. Fantastic letter. I'm so glad you guys wrote it. But what was the conversation like before? Because I've been having conversations with them too, and they go nowhere and it's clear they're not interested. What was it like for you? They said, we didn't have any conversations with them. They wouldn't even reach back out to us to have a meeting. Right. So like. So Biden and Harris refused to even meet with the College Democrats of America, one of the backbones of youth engagement on college campuses when you're trying to win an election and even in off years.

[Aziz Ansari]

Yeah.

[Kal Penn]

And it led them to have to publicly write a letter to the Washington Post. Like, the Democratic Party needs a real realignment of its core values and looking at what young people actually care about. And multiple things can be true. We can stand up for human rights and against anti Semitism. Like these false convers that are being created around it are shocking, I think, you know, to, to a lot of people. And so, so is your, Your example of that is spot on. And it's what I experienced in, in, in talking to a lot of these folks who were organizing. It's like you said at the, the people at the DNC were just put.

[Aziz Ansari]

Yeah, I saw it with My own eyes. And so it was one of those things where I go, I can't in good conscience tell anybody.

[Kal Penn]

Yeah.

[Aziz Ansari]

How they should, because those people were doing, like I said, everything they tell you to do in civics class.

[Kal Penn]

Yeah.

[Aziz Ansari]

Actively engage peaceful protest. Right. Your member of Congress, you know, offer up.

[Kal Penn]

Yeah.

[Aziz Ansari]

A channel of dialogue. Like it was all just outright.

[Kal Penn]

You saw this with Zoran too. Schumer didn't even endorse him. Right. Like mainstream Dems. Hakeem endorsed him, what, like three days before?

[Aziz Ansari]

About three minutes before.

[Kal Penn]

Unenthusiastically.

[Aziz Ansari]

Three minutes while you were in line.

[Kal Penn]

Right, right, right. So. So it only matters. Only support the nominee if it's the right looking nominee.

[Aziz Ansari]

So you personally know Zoran Mandani. You personally know his family, both his father and his mother? What, what does this Zoran moment mean? And as someone who has now worked in politics, how should we meet this moment as citizens of the city of New York?

[Kal Penn]

I think the, the best way to meet this moment, this, this love affair that New York City has either with or against him. If you're a Zoran fan, the things about city politics, the support he's going to need from the governor to get certain policies through from the city council, like know who your city council rep is, make sure you write them letters, send their office emails or phone calls. If you agree with something that the mayor is trying to do, like this is this all now requires actually using the political capital that Zoran earned by getting people out to vote for him and to canvas for him and turning that into real political action. It's one of the, one of the things that both helped and hindered, depending on the extent of it during the Obama years, any presidency. Right. So that's like key number one is looking at those things and being like, yes, I need to, I need to show up and call this person to say, I need you to allocate this money. Just like the mayor wants, that kind of thing.

[Aziz Ansari]

How do people show up for that? What do you mean? It's a great example with like, freeze the rent.

[Kal Penn]

Yeah.

[Aziz Ansari]

Free buses. How do people show up for that?

[Kal Penn]

So couple the biggest. The basic things are like, just know who your city council rep is. Know who your state assembly rep is. Right. Just know who all these people are who support you. They might be very boring or they might, they might be interested. Just know who they are. Maybe follow them and get a sense of whether they're on board with the things that the mayor is trying to do. They're also organized. You don't have to do this alone. There are organizations that, that do this. Zoran's a democratic socialist, so you could follow DSA for, for all of that. You don't have to. There are think tanks, There are great groups like, like make the. If you're an immigration advocate, if you care about immigration rights, like, follow a lot of these just on social. And you'll see in their stories, like, what are they organizing around? Why? What's the margin by which, like you need people to show up. It's like, like all the, the marches that people had, like the, the no Kings thing. Right. So imagine a no Kings march, but there's an actual deliverable, hard goal at the end of it. Like there's a bill that's up for a vote or you need the governor's support for something. So it's like a march like that, but with an actual immediate deliverable. So that's, that's the kind of thing that I think we need to be mindful of.

[Aziz Ansari]

How are the expectations similar or different between say the president and then say the mayor of New York City? How are you looking at it?

[Kal Penn]

I'm looking, I mean, I'm looking at it differently. I didn't know Obama before, you know, volunteering for his campaign. I've known Zoran since he was 14, so that's a little bit surreal also. It's like just so proud of him. Right, right, right.

[Aziz Ansari]

To know him as a person.

[Kal Penn]

To know him as a person and being so proud of him. Yeah, yeah. But I do think the, you know, the, the people who he got, people who'd never been involved in politics to register to vote, to knock on doors. That's a big moment and it's a, it's a real special time for the city, for his administration and then beyond. Most people who are finally registered to vote will continue to register to vote or continue to vote. Right. But it's, it's, it's knowing that all of us need to continue to show up to. Like he can't unilaterally, single handedly get a lot of the stuff done that he wants to get done, but he absolutely can get it done in partnership with this sea of people who came out to support him.

[Aziz Ansari]

So you have a lot of amazing anecdotes in your book. You can't be serious.

[Kal Penn]

Thank you.

[Aziz Ansari]

What Harold and Kumar was to me. Describe what Mississippi Masala was to you.

[Kal Penn]

Oh, man. So Mississippi Masala is a film that Mira Nyer directed. Denzel Washington, Sarita Charlie. I think it was one of Denzel's first movies. It came out when I was probably 13. Yes. 12. 13. Something like that. 8th grade. And I went to see this movie with my parents and my cousin and it was the first time that I had seen brown characters on screen played by brown actors who were fully fleshed out and flawed. Like these people were this family. The family was like struggling, successful, racist. Denzel and Sarita have sex. Like, like things that people actually do in life that aren't one note. And I walked out of there going, if this woman, Mira Nair can do this, then like maybe I can too. Right. This form of. Yeah. Of like, of art. And it, it was one of the big catalysts on, on, on deciding that I wanted to pursue film and TV and acting.

[Aziz Ansari]

In the book you talk about Captain Moneybags.

[Kal Penn]

Oh, yeah.

[Aziz Ansari]

Who was Captain Moneybags?

[Kal Penn]

So you've noticed I've changed some of the names in the book and I've given them all names about how I felt at the time. Yeah. Yeah. So one of my, probably my longest internship in LA in college. Very difficult to get an internship in LA unless you knew somebody. I didn't know anybody. So after like a year and a half of applying through like the UCLA Internship Center, I get a phone call or an email from like this guy who said that he ran a production company at one of the big studios. And I meet with him and it's like on the back lot of, of one of the studios, like meet for coffee. And he's selling hard. He's telling me about all these amazing things he's producing. Yeah. And I'm falling for all of it.

[Aziz Ansari]

Sure.

[Kal Penn]

And he's like, I can hire you tomorrow if you can start. I'm like, yes. So I was going to be a script reader and I would like answer phones and do his emails. And I walk into his office. It is one room, probably about this distance.

[Aziz Ansari]

This is in studio City of Sherman Oaks.

[Kal Penn]

In one of the studios.

[Aziz Ansari]

Okay.

[Kal Penn]

Yeah. Okay. Maybe Culver City. Sure.

[Aziz Ansari]

Maybe so.

[Kal Penn]

So he. It's very clear. There's like one desk in the corner. Yeah. And then two like mini desks for his interns who he's not paying.

[Aziz Ansari]

Okay.

[Kal Penn]

Reason I called him Captain Moneybags is it turned out he was a trust fund kid.

[Aziz Ansari]

Yeah.

[Kal Penn]

Whose dad was one of the big execs at the studio at the time. So he had, he had gifted his son a production company with a first look deal. And I learned more about how not to produce movies from working for this guy for a year than I. Than I ever did. In any of the other, like, internship things.

[Aziz Ansari]

Tell me about the casting process that you went through with him where you had to give him a bunch of headshots.

[Kal Penn]

Yeah, that's right.

[Aziz Ansari]

What happened?

[Kal Penn]

So the one day he goes, we're. We're casting this high concept, low budget horror film. Yes. And I need to find a lead actor who's like. He loved using the word pops. He's like, who's. Who's about to pop.

[Aziz Ansari]

Give me a lead actor that pops me.

[Kal Penn]

Someone who's about to pop. Hasn't popped yet. So I can afford it for very little money.

[Aziz Ansari]

Yes.

[Kal Penn]

But is about to pop.

[Aziz Ansari]

So you hand him a photo of Joseph Gordon. Gordon Levitt.

[Kal Penn]

I hand him Joseph Gordon Levitt's headshot in a little pile. And he gets to Joseph's headshot and goes, what the fuck is this kid Asian? And I'm like, I don't. I don't know. Why? Because I'm not trying to cast fucking Asians in my movie. Cal, bring me good white American actors. And then we, like, move on through the pile. I'm like, well, this is a weird thing to say, because obviously he knows I'm an aspiring actor and he can see what I look like. So it's very bold. And just to be fair, I always appreciate just the straightforward answer.

[Aziz Ansari]

Sure.

[Kal Penn]

Don't fucking sugarcoat your racism. I want to know exactly how you feel so I can find another way in.

[Aziz Ansari]

Now, did Captain Moneybags even know that India is in the continent of Asia?

[Kal Penn]

I don't know if Captain Moneybags knew much beyond his BMW and his house in Malibu.

[Aziz Ansari]

Okay.

[Kal Penn]

But. So I'm gonna say no.

[Aziz Ansari]

Got it.

[Kal Penn]

Right. So I walked.

[Aziz Ansari]

But you're like, be straightforward. Just give it to me real.

[Kal Penn]

Just tell me what you. Right. So. But then I was like, I need to learn, because if this is. If this is how blatant is. So I follow him to his car at the end of the day, and I was like, hey, can I ask you a question? What was the deal with not wanting Joseph Gordon Levitt in this movie because you thought he looked Asian? And by the way, he's not Asian. Not that it matters for this conversation. Sure. Yeah. And he goes, oh, it's simple. Asians don't see movies.

[Aziz Ansari]

He said, asians don't see movies.

[Kal Penn]

Asians don't see movies. Asians don't watch movies.

[Aziz Ansari]

They don't watch film.

[Kal Penn]

Correct. That was his take. Understood. And I said, well, I'm Asian American, and I watch plenty of movies, and everybody I know across A multicultural spectrum. All watches movies. This feels ludicrous. So I'm like, I'm going to leave it alone. I stayed late that night, and I went through. You have access to all this, like, studio demographic data?

[Aziz Ansari]

Sure.

[Kal Penn]

So the nerd in me was like, I got to find this data.

[Aziz Ansari]

Oh, God.

[Kal Penn]

And I saw data. The data under Asian American and Hispanic at the time had an asterisk next to it. But that's not because Asians don't see movies. It's because they don't ask Asians what movies they see. So it was only black or white. Then I pulled census data about spending money. Like, what's it called? Disposable income. Sure. And when he comes in the next day, I'm showing him all of this data. I'm like, dude, actually, Asians have purchasing power on parody with the group that has the most purchasing power in America. Hidden asset here. You actually shouldn't cast Joseph Gordon Levitt. You should cast an actual Asian American actor in this role, and your movie will pop. And he goes, no, Asians don't see movies. So he had the data in front of him.

[Aziz Ansari]

Him.

[Kal Penn]

Right, right. He actually was looking at this going, no, I know better. I know better. Asians don't see movies. So it was just like that bravado. Like, we all know producers like this. Yeah. Yeah. Thankfully, there are less of them.

[Aziz Ansari]

Some version of Captain.

[Kal Penn]

Yeah. So that was. What was wild about. About that story is I just kind of walked away from that going, all right, The. The, like, glass ceiling is so, like, you just can't. There's no way that you're.

[Aziz Ansari]

I mean, it's not even made of glass. It's steel.

[Kal Penn]

Yeah.

[Aziz Ansari]

You're not getting through the steel.

[Kal Penn]

But I'm. I'm glad he was honest and learned. You know, I learned a lot about it.

[Aziz Ansari]

What did you take away from that moment either empower you or were you like, look, I cannot change someone's preset biases, so why even try? There's two potential paths here.

[Kal Penn]

But it was both. Both things were true. Right. I was a. I was livid.

[Aziz Ansari]

Yeah.

[Kal Penn]

And I was. I was mad because I'm like, oh, this is what I'm up against. Yes. Right. It's like. It's one thing to, like, oh, you put a screen name. You go from Culpin Modi to Calpen on your resume because you think it might open a few more doors. And maybe it does, maybe it doesn't, but those are the things you have control over. But then what? This guy was Showing me was that that didn't even matter for, like, guys who were, who were like that. Then on the flip side, it was like, you're, you're, you're illustrating to me that the, the standard way of doing things isn't going to work. Right. So I have two choices. I can be a bitch and lament and whine about how this isn't going to work out, or I can strategize about a different way in. Right. And so both of those things were true.

[Aziz Ansari]

You are one of the nicest people in Hollywood. I have never heard a bad story about you.

[Kal Penn]

Oh, thank you.

[Aziz Ansari]

Why are people in Hollywood.

[Kal Penn]

I've heard a lot of bad stories, but. No, I'm just kidding.

[Aziz Ansari]

I mean, you've heard them, you've read them. They're at the top of the Google charts.

[Kal Penn]

They're there still. You didn't wipe them.

[Aziz Ansari]

There's nothing you can do. There's nothing you can do.

[Kal Penn]

Cal, I'm kidding.

[Aziz Ansari]

You're one of the most liked people in Hollywood.

[Kal Penn]

Thank you.

[Aziz Ansari]

Why are people such assholes?

[Kal Penn]

I don't know. I don't know.

[Aziz Ansari]

What do you think their incentive is?

[Kal Penn]

I'm going to tell you this, and I'm not trying to flip it, and maybe I'm leaning into the stereotype of me being too nice. There are so many filmmakers who just want to work with nice people and who like, like they want to work with, with, with good folks. I have. I'm not saying this to plug it. It's true. I'm on season four of Industry, which comes out in January. Mickey and Conrad, the guys who created that. Right. You don't know what you're getting walking into a show that already exists and has that much critical acclaim, and you walk in and people are like, like immediately having artistic conversations with you. It's a no bullshit zone. Mike Schur is the same way. He EP my show Sunnyside a couple of years ago for NBC. Like, there's this whole caliber of people who, by the way, to me, asshole. Ishness is insecurity. That's why people are such dicks sometimes.

[Aziz Ansari]

Yeah.

[Kal Penn]

You know, like, like if you're.

[Aziz Ansari]

Oh, you're, you're masking something.

[Kal Penn]

You're masking your insecurity.

[Aziz Ansari]

You're overcompensating 100%. You're ins.

[Kal Penn]

Opposed to, like, somebody who is kind and collaborative and knows what they want. Like, if you have. It doesn't undermine your artistic vision to be kind. It just brings out everybody's artistic vision. And then you're the director, you still decide at the end of the day, but that's been my experience is that. Is that dickishness is just pure insecurity or entitlement.

[Aziz Ansari]

You know, you have had to craft a path where you're kind of like in the jungle, and you have a machete, and you got to clear the brush out. There is no path set for you in the book. You can't be serious. You talk about your story auditioning for Van Wilder.

[Kal Penn]

Yeah.

[Aziz Ansari]

It honestly feels like a piece of fiction. It feels like something that was literally made up. You cannot do this today.

[Kal Penn]

Right.

[Aziz Ansari]

Who were you testing against in the film? Van Wilder for your role.

[Kal Penn]

So in the final callback for Van Wilder, in which I play a character named Taj Mahal.

[Aziz Ansari]

Taj Mahal.

[Kal Penn]

So he's not even named after. He's named after a building. Yeah. Also, fun tidbit. His last name is Bada Landabad.

[Aziz Ansari]

Oh, geez.

[Kal Penn]

Yeah, yeah, yeah. Which I enjoyed. I thought that was.

[Aziz Ansari]

So Taj Mahal is first name, middle.

[Kal Penn]

Name, first name, middle name. And then that's his last name.

[Aziz Ansari]

All right.

[Kal Penn]

Which basically means, like, big Cock.

[Aziz Ansari]

Big Dick.

[Kal Penn]

Yeah. So I knew at the end, it was like, all right, it's me and another actor. I'm like, which brother is it? Like, you know, I'm sure, sure, sure. And I'm excited that one of us is going to get this.

[Aziz Ansari]

I feel like you're going to open the door. You're going to see Asif Manvi, somebody. Somebody that you know. Yeah.

[Kal Penn]

So I open the door, and it is a white dude in brown face who's already in the waiting room. And my beef is generally not with other actors. Actors are desperate. We'll take. We'll do whatever it takes to get a part. Right. But I was so fascinated. I'm like, okay. Did his agent tell him to, like, paint his face when he left? Did he do it at home, or did he do it in the bathroom? If he did it at home, did it increase his chances of getting pulled over by the cops? Like, all of these thoughts going through my head and.

[Aziz Ansari]

But he was full, Trudeau.

[Kal Penn]

He did the whole thing full, full.

[Aziz Ansari]

Full arms and hands too.

[Kal Penn]

Full, full, full.

[Aziz Ansari]

And you don't have to name names, but is it a. He's not actor.

[Kal Penn]

No, he's not an actor anymore.

[Aziz Ansari]

Oh, okay.

[Kal Penn]

He, I think, moved back home somewhere in the Midwest. I did look him up when I was writing the book. Sure. I thought maybe there's a fun quote.

[Aziz Ansari]

Or did you guys do that thing where you, like, before you test. You're like, hey, man, what's going on?

[Kal Penn]

Yeah.

[Aziz Ansari]

Oh, fully, dude.

[Kal Penn]

Full small talk. Full small talk. We even hung out a few times after that.

[Aziz Ansari]

You didn't mention the shoe.

[Kal Penn]

Did not mention that.

[Aziz Ansari]

Okay.

[Kal Penn]

Also, it wasn't uncommon in those days. So I realized telling it now, and it's only been 20 years, telling it now, you're like, oh, my God, people did brown face. Right. Like the new. The new Aladdin a couple of years ago had brownface with a bunch of extras. Right. So, like, it does still happen, obviously, in a totally different way, but it was common enough. Right, Right. But I do remember looking at him while we're making small talk, and in my head, just saying to myself, he is not allowed to get that part. You're like.

[Aziz Ansari]

You're like, I have to do this.

[Kal Penn]

I have to do this. And I had questions about whether I wanted to do it if I got the part anyway. Right.

[Aziz Ansari]

You talk about this in the book, and it represents this kind of divide that is also common in political discourse.

[Kal Penn]

Yeah.

[Aziz Ansari]

Number one, do I stick with my principles? Ten toes down, zero compromises? Or number two, do I compromise some things to benefit a larger goal later on?

[Kal Penn]

Yeah.

[Aziz Ansari]

You went with the latter.

[Kal Penn]

I went with the latter.

[Aziz Ansari]

Why is that important?

[Kal Penn]

So I am never going to throw shade on people who choose the former, because a lot of people do, and they're very successful in their own right. I chose the latter at that particular time, you know, early 2000s, at that point in my career. Yeah. Because the advice that I got, not just from my agent at the time, but there was a wonderful woman named Sonia Nakor who is no longer in the business, but she was the only Indian American casting executive at NBC. At NBC.

[Aziz Ansari]

Yeah.

[Kal Penn]

And I had a general meeting with her and she was like, if I can ever offer advice, give me a call. I had no reason to call her until this. And I was like, there's this movie called Van Wilder. It's a supporting lead if I get the part. But he's named Taj Mahal. He's an exchange student. They want, like a stereotypical accent. I don't know what to do. She goes, well, a couple things here. One, if you get the part, it is true that your agent will be able to pitch you for things that require you to have had a supporting lead role on your resume. That's just true. Doesn't matter the nature of the role. But number two, like, how many things in the script are, like, cringe worthy? I was like, I don't know, like 30. She goes, OK, OK. That's a lot. So you. You need to pick 10. All right? Pick 10 things in the script that you think are cringeworthy. And. And then if you get the part, you talk to the director about them. And I interrupted her, and I was like, oh, shit. I didn't know this was the thing I could do. She's like, I'm not done. You need to come up with 10 things that are funnier than what the writers came up with if you're going to do this. Because you have to understand that nobody is making this movie and writing that character with the purpose of offending somebody or promoting a stereotype. They think it's funny, they think it'll make money, and they think it'll make audiences laugh, period. So it was the first time somebody showed me how I could have agency in the conversation. So I'm like, it. Let's see.

[Aziz Ansari]

What a gem, though, to be like. To be like. You need to come up with a better idea.

[Kal Penn]

Yes.

[Aziz Ansari]

You actually have to.

[Kal Penn]

That's your job, literally.

[Aziz Ansari]

You can't just be like, I'm not doing that.

[Kal Penn]

No.

[Aziz Ansari]

I'm shutting this down. You have to exceed what is on the page here.

[Kal Penn]

And that hadn't always worked. Right. And it hasn't since. But so. And then, you know, to walk in and see the dude in brownface, I was like, decision made. If I get this part, I'm taking it. I'm taking this part. I need the credit. And. And then I got the part. I mean, this segues a little bit into Harold and Kamar. If you want, like, the longer version of the story, let's do it. So. And Ryan Reynolds was wonderful. We improvised in the audition. I did talk to the writers. There were 10 things they dropped that I added. Right. All of that was. Was fine. And it was what it was. A couple of years go by, and the audition for the Harold and Kumar movies, or Harold and Kumar Go to White Castle, comes up. There's no shortage, by the way, of Brown actors to play Kumar. They audition people in la, Montreal, London, New York, Sydney, everywhere. And one of the reasons I got the job is because I was the only guy who had a supporting lead role on my resume. Because I had done Van Wilder, you.

[Aziz Ansari]

Had done a big studio comedy, right?

[Kal Penn]

And so that. That really moved the needle forward. And it took a couple years for me to fully realize that. And had I not done Harold and Kumar Go to White Castle, I would not have had the chance to do the Namesake because. So Mira Nair, right? Mentor of mine, even though she didn't know it since I was in middle school. I see that they're doing the Namesake. John Cho actually recommended Jumpa's first book. We read it together. Read the Namesake together, tried to get the rights to it, found out Mira Nair beat us to it. So I had my agent like beg for an audition for the Namesake for the lead, and they can't get me in the room. So I hand wrote her a letter and I mailed it. That was basically like, you've been a mentor for years. You're one of the reasons I decided to be an actor. Yeah, you have to let me audition for, for the Namesake.

[Aziz Ansari]

You know, very rarely this works. Right.

[Kal Penn]

Of course, I had done it before and yeah, this is the equivalent.

[Aziz Ansari]

This is the equivalent of sliding in the dms.

[Kal Penn]

Yeah, exactly.

[Aziz Ansari]

But way more work, by the way.

[Kal Penn]

What? That. It's handwritten.

[Aziz Ansari]

Yeah, handwritten. And you got to. You got to put Creative Arts Agency. You got to do the whole. You got to do the whole thing.

[Kal Penn]

Do the whole thing. So. So I send this off and a week later my manager calls, hey, Mira called and you gotta fly out to New York, you have an audition for the Namesake.

[Aziz Ansari]

Okay?

[Kal Penn]

And I get there and she goes, look, the biggest reason you're here, I got your letter. And for the last six months, my 14 year old son Zoran has been telling me that I should audition you for the lead and the Namesake. And he's shown me clips from Harold and Kamar Go to White Castle. And I just thought, this is the most puerile thing I've ever seen. You're clearly the wrong choice to play Gogol, the lead in my independent drama. But then I got your letter and so I'm happy to have you audition. And if you wouldn't mind sticking around to meet my son after the audition, that'd be great. Like, what a. What a world, right?

[Aziz Ansari]

So this is what I'm telling you. Full circle moment.

[Kal Penn]

So.

[Aziz Ansari]

So for me as a 19 year old and for him as a 14 year old, for Zoron as a 14 year old, how seminal this was it.

[Kal Penn]

It was. I mean, and I'm telling you, the crazy business story behind it, right? The question about whether to be a purist and say no to things or whether to do what you hope is an investment. So had I not said yes to Van Wilder would not have gotten. I mean, maybe I still would have gotten Harold and Kamar, who knows? But probably would. May not have gotten Harold and Kumar. Hadn't done Harold and Kumar Certainly would not have gotten in. In the door for the Namesake. Or maybe I would have because Mira wouldn't have seen the clips. Like, you never know. But. But that was the trajectory of what that meant. And the Namesake is my favorite thing I've ever done.

[Aziz Ansari]

You have two new podcasts.

[Kal Penn]

I do.

[Aziz Ansari]

I don't know why you have two podcasts, but you have two podcasts. You have one which is Ears say the Audible and I Heart Audio Book Club.

[Kal Penn]

Yeah.

[Aziz Ansari]

Which you co host with Ed Helms.

[Kal Penn]

I do.

[Aziz Ansari]

And then of course, you have Here We Go Again, an interview podcast that lets you just nerd out about politics, science, and culture.

[Kal Penn]

Yeah.

[Aziz Ansari]

So you have a book club and you have your own podcast.

[Kal Penn]

Yeah. Let me do my own podcast first. Sure. Let me plug this. I did not.

[Aziz Ansari]

Why? Two podcasts.

[Kal Penn]

The second one is just because I'm a book reading, audiobook fan and I heart was like, hey, can you host this thing on the side? It's like book podcast with Ed.

[Aziz Ansari]

Okay.

[Kal Penn]

Yeah, sure. So I think it's like eight episodes, really fun. Okay. But it's very literary and was kind of an offshoot of Here we Go again. Yeah, I didn't. I also, by the way, didn't think I was going to host a podcast. You know how crowded the space is. Yours is phenomenally successful, but everybody has a podcast and they're not always like, the most, you know, they don't. They don't often peak. So I was a little self conscious about that. I'm like, until I have an angle or a story that I really want to tell. So I'm not good at, like, for politics. I'm not good at, like, going on cable news and screaming at people. That's not what I do. Maybe because I'm too nice, like you said. And so Ed's company reached out and was like, hey, we want to brainstorm a podcast about pop culture, history, and politics, but why cycles keep repeating itself. And a lot of this was like our conversation about Obama, Zoran, all of that. Right. How do you look back at things? What do you learn from? And I'm like, this is fun for me because it can be uplifting, it can be funny, and you can without being preachy. You can kind of learn something from it. So, like, our first guest was Bill Nye to talk about the space legend. Right. My questions for him were, in the 80s, space race was us versus the Soviets because we were trying to kill each other. Now it's like, which billionaire has the biggest dick? Is like the new space race Right. So talk me through that. Where are we going from here? It's basically that kind of a thing for. For different topics throughout pop culture and history.

[Aziz Ansari]

And then the book club is just a book club.

[Kal Penn]

Book club's a book club with, like, really fun audio books. Like, and the narration is great. Like, Kerry Washington did one of these, and Ed is very, very funny. So to talk to, like, there was one. One about Mark Ronson or for Mark Ronson's new book audiobook that. That he narrates.

[Aziz Ansari]

The musician Mark Ronson.

[Kal Penn]

Yeah, yeah, yeah. And Questlove was our guest for that. They know each other really well. So it's kind of like, if you've listened to this audiobook, to get like, a. A real angle into. Into the making of it and the story behind the story.

[Aziz Ansari]

4Th Eldon Kumar. Yeah, dude, let's go.

[Kal Penn]

Let's go. They made a deal with the writers. They're working out the deal with myself and John. Okay. Obviously, I would make it. I hope so. We don't have, like, a sign, but you're downtown. I'm super down.

[Aziz Ansari]

John's in.

[Kal Penn]

John is in. As far as I know. Yeah.

[Aziz Ansari]

Okay.

[Kal Penn]

You need to do a cameo.

[Aziz Ansari]

I'll call me for whatever.

[Kal Penn]

All right.

[Aziz Ansari]

I'll do it for day. Right.

[Kal Penn]

Well, they might ask you to.

[Aziz Ansari]

This is great.

[Kal Penn]

Thank you. Thank you for having me.

[Aziz Ansari]

Of course. Have you subscribed to Lemonada Premium yet? You can listen completely ad free and get access to exclusive bonus content you won't hear anywhere else. Like my discussion with Malala on how therapy changed her life. Or my convo with Mel Robbins on how her let them theory applies to parenting. Tap. Subscribe on Apple podcasts or head to lemonadapremium.com to sign up on any app that's lemonadapremium.com.