368: Jay Chandrasekhar | The HoneyDew with Ryan Sickler #368 | Full Episode

Summary

Podcast Summary: The HoneyDew with Ryan Sickler #368 — Jay Chandrasekhar

Release Date: January 12, 2026
Host: Ryan Sickler
Guest: Jay Chandrasekhar (comedian, director, writer – best known for "Super Troopers" and member of Broken Lizard)

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Episode Overview

This episode of The HoneyDew welcomes filmmaker and comedian Jay Chandrasekhar for an in-depth, hilarious, and heartfelt exploration of his upbringing as the child of Indian immigrants, his experiences with tradition and assimilation, and his unique journey to breaking barriers in comedy and film. The conversation dives into family lore, cultural conflicts, early experiences with race and identity, and the relentless resourcefulness it took to carve out space in show business—as both a South Asian actor and director.

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Key Discussion Points & Insights

1. Early Life & Family Dynamics

• Upbringing in Chicago:

  • Jay was born and raised in Chicago, Illinois (08:01), an area with very few Indian families at the time. Both parents were doctors, working at Cook County Hospital.
  • Jay describes his parents’ immigration journey, academic excellence (both were top of class at medical school in India), and the strictures of Indian caste and tradition (08:23).

• An Unorthodox Love Story:

  • Jay’s parents met in the U.S. after emigrating separately from India. His father decided to marry his mother upon meeting her, which defied the expectations of arranged marriage common in their families (09:04).
  • Jay recounts how his grandmother tried to bribe his mother with $10,000 in diamonds to break it off (09:54), but his parents proceeded—and his grandmother moved to the U.S. to help raise Jay and his sister.

• Clashing Traditions:

  • Jay’s family’s caste differences and disregard for arranged marriage created longstanding family tensions (10:42).
  • "My grandmother never quite got over it, you know, she never quite got over the fact that she didn't get to pick." (Jay, 11:06)

2. Indian-American Upbringing

• Cultural Outsider:

  • The Chandrasekhars were the only Indian family "for miles and miles" in suburban Hinsdale (19:14). Jay says their social status as doctors helped insulate them from discrimination:
    • "We were coming in at a financial level that was confusing, I think, to people... we were always treated with immense respect." (Jay, 19:20)

• Racial Dynamics:

  • Jay gives an honest, nuanced take on 1970s/80s American childhood—where racism was present but not always directed at him.
    • "The worst it got for me as a kid was my best friend... said, 'you're brown because your mom left you in the toaster too long.' And I said, 'you're white because your mom didn't toast right.'" (Jay, 20:15)
  • He acknowledges never feeling excluded by his peers’ families, but shares stories about cultural difference in dating and the subtle barriers to being seen as the "desirable" guy.

• Leaning into Humor:

  • Jay discusses how being perceived as “different” pushed him to develop his comedic voice:
    • "I had to pull off hooking up with white girls as not their ideal image of what, you know, because all girls in the country are fed Sean Cassidy..." (Jay, 23:17)
    • "It probably made me really lean into the funny because... I was valuable." (Jay, 23:22)

3. Education, Early Comedy, and Parental Expectations

• Schooling:

  • Jay attended boarding school in high school. His mother enrolled him after reading about bullying of minority kids in public schools (27:12).
  • Despite some challenges, including a "narc" incident (where he reported a roommate for smoking weed and was then ostracized), theater became his refuge and launchpad (31:33).

• Discovering Comedy:

  • Jay developed his performance skills in high school plays and broadened his comedic abilities at Colgate University and later in Chicago’s improv scene (33:00).
  • Stand-up and improv led to his decision: "If I can make strangers laugh, I'll give this career a try." (34:01)

• Parental Reaction:

  • Coming from a family of high-achieving doctors, Jay’s pursuit of comedy was seen as baffling:
    • "Why would they want a junkie B plus Indian with all these good A plus Indians to choose from?" (Jay, imitating his dad, 34:01)
    • He agreed to his parents' deal: "Four years, go to law school if it doesn't work out." (42:44)

4. Barriers in Hollywood & Breaking Through

• Creating His Own Path:

  • Jay quickly realized, “The only way I'm gonna get on the screen is if I write my own scripts and put an Indian in the middle of the movie, and then they'll have to cast me. And then... I better direct this movie." (Jay, 35:44)
  • He co-founded Broken Lizard, raised money, wrote, and starred in “Super Troopers,” forcing his way into film.

• Industry Resistance:

  • Studios wanted bankable white stars: "I'll give you the money, but Ben Affleck has to play that part. Thorny. And I'm like, that's my part." (Jay, 37:13)
  • Success of “Super Troopers” ($1.2M budget, sold for $3.5M) allowed him to continue both acting and directing.

• Changing Stereotypes:

  • Jay discusses how white writers’ memories—"writing for the memories of their high school"—shape characters and opportunities.
    • "When you play long Duck Dong, you're not gonna be the guy who eventually... is Jennifer Aniston in some other movie." (Jay, 48:11)
    • He connects increased diversity in writers' rooms to more authentic representation on screen (55:01).

5. Perspectives on Racism and Progress

• Notable Quote:

  • "Not everything is racist. You know, like, there are things that are a little racial, but that's a little bit natural human behavior." (Jay, 45:04)

• The American Dream:

  • Jay expresses gratitude for his breakthroughs and the openness of American audiences:
    • "I always say the country is very big hearted, that it was like, sure, great, fine, that's funny. Funny's funny, right?" (Jay, 50:29)

• On Show Business:

  • "Show business is like a tiny island of success in a vast ocean of rejection." (Jay, 51:52)

6. Hollywood Anecdotes & Directing 'Dukes of Hazzard'

• General Lee & the Confederate Flag:
  • Jay got to direct "Dukes of Hazzard,” including major stunts and car jumps (56:44).
  • He grappled with the question of removing the Confederate flag from the General Lee:
    • "There's no way this Indian's gonna be the guy who takes the roof up, man." (Jay, 60:52)
    • Ultimately, the film acknowledges the controversy within the narrative.

7. Advice to His Younger Self & The Entourage Story

• What Jay Would Tell 16-Year-Old Jay:

  • "Treat the guys from Entourage with respect." (Jay, 63:50)

  • Jay narrates a story about blowing his chance to direct "Entourage" due to dismissiveness, realizing in hindsight the importance of humility and open-mindedness toward new creative opportunities.

  • Notable lesson: "Just, they're trying something creative. The pilots are always hard. Be open-minded. But what were you going for? ... We can make it better this way." (Jay, 68:53)

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Notable Quotes & Memorable Moments

• On Hollywood’s resistance:

  • "If I had been a white actor, I would have never learned how to write. ... That cute girl coming up to me like, you're cute. You want to make out? Like, that didn't happen to me. That wasn't going to happen for me in show business." (36:48)

• On Representation:

  • "The job of the people like me is to change minds." (49:31)

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Highlighted Timestamps

| Time (MM:SS) | Segment / Topic | |------------------|---------------------------------------------------------------------| | 07:52 | Jay describes his parents’ journey and love story | | 09:54 | $10,000 bribe in diamonds to break up his parents | | 19:14 | Growing up as the only Indian family in the area | | 20:15 | Childhood jokes, navigating race and friendship | | 23:17 | Dating challenges and humor as survival | | 27:12 | Moving to private/boarding school due to fears of bullying | | 31:33 | The infamous “narc” incident – reporting his roommate | | 33:00 | Discovering performance and comedy | | 35:44 | The necessity of writing/directing to create one’s own opportunities| | 37:13 | Studios wanting to cast Ben Affleck in his own role | | 42:44 | The deal with his parents: “4 years, then law school” | | 45:04 | “Not everything is racist.” | | 50:29 | The country’s “big-hearted” embrace of his comedy | | 51:52 | “Show business is a tiny island of success in a vast ocean of rejection.”| | 56:44 | Directing "Dukes of Hazzard" and dealing with the General Lee flag | | 63:50 | Advice to his younger self: “Treat the guys from Entourage with respect” | | 68:53 | On failed opportunities and open-mindedness in creative work |

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Closing Thoughts

This episode is a masterclass in perseverance, adaptability, and cultural navigation. Jay Chandrasekhar shares hard truths—about being an underrepresented “outsider,” about the hurdles to creative visibility, and about the paradoxes of assimilation and tradition. Yet, his storytelling is as warm and irreverent as it is inspiring—a testament to how great comedy is born from both pain and possibility.

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Jay’s Plugs (repeated at end):

• Live shows at the Arlington Drafthouse (August 7–9)
• App: Vouch Vault (recommendation/sharing platform)
• Podcast: Mustache Tales w/ Hayes MacArthur

Host: Ryan Sickler (@RyanSickler on all socials)

Transcript

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[Ryan Sickler]

Kansas City. I'm headed back your way. Valentine's weekend. That's right, Valentine's weekend. I'll be there February 13th and the 14th. Connecticut. Come see me at Comics Roadhouse March 13th and 14th. Get your tickets now at Ryan Sickler.com the Honeydew with Ryan Sickler. Welcome back to the Honeydew, y'.

[Jay Chandrasekar]

All.

[Ryan Sickler]

We're over here doing it in the night Pan studios. I'm Ryan Sickler. Ryancickler.com Ryan Sickler on all your social media and starting this episode like I start them all with gratitude. Thank you. Thank you for watching this show. Thank you for supporting this channel. If you're watching this far, drop a comment, help it all out. And if you gotta have more, then you gotta have the patreon. All right. It is this show. It's the Honeydew with y'.

[Jay Chandrasekar]

All.

[Ryan Sickler]

And y' all have the craziest stories I've ever heard. I've been promoting this show for years. It's five dollars. That's audio and video for five bucks. All right? And you get the Honeydew a day early ad free, no additional cost. We got another tier where you get the way back a day at early ad free, no additional cost. All right.

[Jay Chandrasekar]

Don't.

[Ryan Sickler]

No sensors, all that stuff. All right, $5. It will remain $5. If you or someone you know has a story that has to be heard, please submit it to honeydewpodcastmail.com and hopefully we'll get to do your story. All right. That's the biz. You know what we do here? We highlight the low lights. And I always say that these are the stories behind the storytellers. I'm very excited to have this guest on here today. Ladies and gentlemen, please welcome Jay Chandrasekar. Did I get it right?

[Jay Chandrasekar]

Nailed it. You nailed it.

[Ryan Sickler]

Yes, sir. Did I really?

[Jay Chandrasekar]

You really did. Thank you.

[Ryan Sickler]

You really, Jay, it's a pleasure to have you here. Before we dive into whatever we're going to talk about today, right there, plug everything you'd like, please.

[Jay Chandrasekar]

I'm at The Arlington Drafthouse August 7th 8th and 9th. I'll be doing five shows. Come on by, hear my Burt Reynolds stories, my Willie Nelson stories, and my lots of drug and drinking stories. I have a podcast called Mustache tales with Hayes MacArthur. You know, it's a podcast. It's funny. And then I have an app called Vouch Vault, which is my revenge machine against Rotten Tomatoes, and it's a recommendations app. So you go on there, you follow me, you find out all the movies, all the tv, all the books, all the restaurants I love. You put your own stuff in there. People follow each other, try to make the sort of the Instagram of recommendations.

[Ryan Sickler]

Okay, cool. You created that app.

[Jay Chandrasekar]

I created the app with two other guys.

[Ryan Sickler]

Okay, great. So you can go on there, and if these people are saying it sucks, it's like, oh, let's see what this group of people saying over here.

[Jay Chandrasekar]

Well, the whole premise is that, you know, my film Super Troopers was, like, the toast of Sundance in 99. And then when it came out, it got a 36 fresh rating on rotten Tomatoes. And this is from the New York Times, the pack paper I read every day. And I was like, gosh, humiliating. Like, this is like. Because, first of all, the audiences at Sundance loved it, and the audiences all over the country, I mean, loved it. Now, I'm not saying that out there, we all love. Yeah. No, I'm not saying that to say I made a great movie. I'm saying the reaction was generally elation, right? Laughing. Ah. And then these critics came out, and I was thinking to myself, back in 2000, I'm like, who are these critics? Like, do they smoke weed? Do they drink beer? Do they eat pizza? Who are they? Like, I don't know.

[Ryan Sickler]

Made a film.

[Jay Chandrasekar]

Well, they're strangers, right? And the point of the app was like, when's the last time you walked up to a stranger and said, what movie should I see right now? You don't do that. You ask your friends and your family and your people who you trust. Tarantino, he makes a list. You're like, okay. That's what this. This app is built to do. It's built to get recommendations from people you know.

[Ryan Sickler]

Got it.

[Jay Chandrasekar]

That's it. All right.

[Ryan Sickler]

And it's just for movies right now or every restaurant, anything, Anything. Okay?

[Jay Chandrasekar]

So if you go on the road to Arlington and you go have a cheeseburger after, you're like, this is a great gastropub. Put it in. And then when I'm in Arlington, I.

[Ryan Sickler]

Look up, say, that's a great idea, especially for us on the road I'll be like, what did Jay go here? Oh, you like this spot here?

[Jay Chandrasekar]

Yeah. Brothers are on it. They're.

[Ryan Sickler]

What's it called again?

[Jay Chandrasekar]

Vouch Vault.

[Ryan Sickler]

Vouch Vault. All right. I'm definitely gonna.

[Jay Chandrasekar]

If you like a comic, put it on there.

[Ryan Sickler]

Yeah.

[Jay Chandrasekar]

Rory Scoville.

[Ryan Sickler]

Yeah. That's great. For example, let's dive into your story here, bud. Originally, where are you from? Let's start there first. Where are you born?

[Jay Chandrasekar]

I was born and raised in the. In Chicago at Cook County Hospital. My parents were both there. They were both doctors at Cook county at the time.

[Ryan Sickler]

They were.

[Jay Chandrasekar]

Okay. Yeah. Yeah. They came over in the 60s. Like, 63, probably 63.

[Ryan Sickler]

And are they married or together at the time? When they come over separately, they were here.

[Jay Chandrasekar]

No. My dad was number one in his class at Madras Medical School. He came over to New York, ended up at Cook county, number one.

[Ryan Sickler]

How many do you even know?

[Jay Chandrasekar]

I don't even know my mom, one year later, was number one. In the same school? No, same school. So she comes over, and they didn't know each other. Didn't know each other. But my. My mom had a buddy who was. Was in the same year as my dad at Cook county. And she called him. You know, she landed, like, some. Like, one in the morning in February, and. And she's like, what the fuck is going on? And, you know, like, there was, like, a guy who was out of money at o' Hare Airport. Hard to believe he's homeless, but she gave him her. Then she called my dad's buddy, and, like, I'm coming in a cab, you guys. You better be waiting for me outside. And my dad, he heard she was hot, so he sort of came down to check out the new chick. And he saw her, he goes, I'm going to marry that girl. And what ended up really happening is they started dating, and he got her pregnant. And now he has to call his mother, who's back in India, and he's like, listen, I'm thinking about marrying this Indian woman here. And she's a doctor and all that stuff. And my mom is in a higher caste than my dad. Right? Like, is that right? Like, we're. We're. We're Brahmins, but they're levels of Brahmins, okay? So she's, like, a little snootier. And my grandmother, though, is still like, you don't pick your wife. I pick your wife.

[Ryan Sickler]

Is that right? I wanted to ask you about that. So it's the. It's the matriarch of the family that Chooses the partner.

[Jay Chandrasekar]

So the. My dad's like, now she's looking at. He's looking at. My mother is six months pregnant. And he goes. He goes, yeah, I'm gonna. I think I'm gonna marry her anyway. And she goes, now, now she goes, put. Put her on the phone. And she gets on the phone, and my grandmother offers my mother 10,000 in diamonds to walk away.

[Ryan Sickler]

No.

[Jay Chandrasekar]

In diamonds. Indians have a lot of jewels. Indians have a lot of jewels. 10 grand. 10 grand in diamonds to walk away. And my mom is like, are you going to tell her? And so he gets on the phone, she's pregnant. And my grandmother says, I'll be there in two weeks. And she moves to America. That moves. I mean, two, three, whatever the number of weeks is, and she moves there. And both parents are doctors, so they're. They have to go to work. And so my grandmother basically takes care of my sister and then me.

[Ryan Sickler]

Your sister's older?

[Jay Chandrasekar]

Yeah, a little older.

[Ryan Sickler]

Yeah. So she ends up approving. Or is she.

[Jay Chandrasekar]

I mean, to some degree, my mother really is the one who took care of my grandmother through. In the end and throughout her life, really made sure she was happy and successful. But my grandmother never quite got over it, you know, she never quite got over the fact that she didn't get to pick.

[Ryan Sickler]

Yeah.

[Jay Chandrasekar]

And so they all always had, like, a. A conflict. There was always a conflict.

[Ryan Sickler]

Were your parents together and had a good marriage?

[Jay Chandrasekar]

Yeah. So they were together till the end.

[Ryan Sickler]

See, I. I've. I watched the documentary Meet the Patels.

[Jay Chandrasekar]

Yeah. And I know that dude, Ravi.

[Ryan Sickler]

You do?

[Jay Chandrasekar]

Yeah.

[Ryan Sickler]

And what I was blown away by was the arranged marriages. They still. Like, when you see them years later, they're still laughing with each other. They're still in this documentary, still having fun with each other. You're seeing that. What I was surprised by was the sort of success rate that an arranged marriage had versus a what we call traditional here. But also, I know that's one documentary for the POV of this director and filmmaker, and that might not be the case for everyone, but I was blown away that these people went along with it. It's still that tradition.

[Jay Chandrasekar]

Yeah. I mean, my uncles, aside from my father, my uncles were all in arranged marriages.

[Ryan Sickler]

And did it work out?

[Jay Chandrasekar]

One of them got divorced and the other two stayed.

[Ryan Sickler]

Are they staying? Like a lot of American couples stay?

[Jay Chandrasekar]

Because who could know, right? And then there are other. My. Some of my cousins, A few of them got arranged and one of them, or two of them ended up in divorce. So I. I think the, the idea is super antiquated. Like there's no way I would ever get. I mean, in fact, when I went to India when I was 20, I was sitting there having, you know, coffee with my mother and her, her best buddy from medical school in Madras, south India, and the doorbell rang. And this hot little like, you know, 19 year old rolls in with her mother and they sit and we chat, okay. Boom, they leave. And then, you know, about 10 minutes later, like, you know, a 17 year old walks in with her mother and I'm like, what's going on? And four or five different women came in and they're like, look, you're, you know, you're Indian in America and you're like a pretty good idea here. Do you like one of these girls? You know, I'm like, I'm 20, man. No, absolutely not.

[Ryan Sickler]

They want you to lock down early, huh?

[Jay Chandrasekar]

Well, my, my mom was like, is.

[Ryan Sickler]

It all about family? Is that what it is about?

[Jay Chandrasekar]

They were all like, or. And my mom was like, I know you're not. I mean, she goes, I, I told them no. She was, I'm not trying to arrange your marriage. I know you, of course we're not going to do that. But they had to take a shot at you. They're still coming by the house. I mean, there's no scenario where I could marry somebody I didn't really know that well. Like, I don't know how you, I don't know how they do it. I get why they do it, but I don't know how they do it.

[Ryan Sickler]

So then is your dad sort of a black sheep? Is he the first one to buck that trend into tradition condition in the family? He is, yeah.

[Jay Chandrasekar]

I mean, but he's, you know, black sheep is, is interesting. I mean it's, nobody ever mistreated him for it, but at the core he got a chick pregnant and then married.

[Ryan Sickler]

And not one that someone said, this one pray. Yeah.

[Jay Chandrasekar]

And my mother was always like, even though she was a very like liberal and open minded person, she was like, I'm higher cast than him.

[Ryan Sickler]

That's what I want to ask you. So she's higher cast than your father.

[Jay Chandrasekar]

Is, who's by the way, plenty high.

[Ryan Sickler]

So how were your paternal grandparents with that? Were they like, whoa, My grandmother was.

[Jay Chandrasekar]

The only one left. The other ones had all died and was.

[Ryan Sickler]

She approved.

[Jay Chandrasekar]

You know, she liked that she was a higher cast, but she really was burned that she didn't get to pick her husband's, her sons.

[Ryan Sickler]

I'm sorry, you're, you're You're. How about your dad's parents?

[Jay Chandrasekar]

Oh, no, they were. They were gone. They were dead.

[Ryan Sickler]

They were both gone.

[Jay Chandrasekar]

They were dead.

[Ryan Sickler]

Okay, so now you have two parents. They. When do they get married? Are they already married when they have you?

[Jay Chandrasekar]

Because they get married before my sister was delivered. Okay. Although that doesn't make sense.

[Ryan Sickler]

Yeah, right.

[Jay Chandrasekar]

Because. Because either they got. Because I've seen the wedding photos and my mom is skinny. Makes me think they must have gotten married after.

[Ryan Sickler]

In between you guys.

[Jay Chandrasekar]

Well, yeah, must have. Must have, because it just doesn't add up. And it's the first time.

[Ryan Sickler]

You're doing the math right now.

[Jay Chandrasekar]

I'm like, wait a minute, she wasn't pregnant in those pictures, so my sister must have been born out of wedlock. There's no other. There's no other explanation.

[Ryan Sickler]

So your dad's man, he's got a lady, he picked himself pregnant out of wedlock, gets married, gets her pregnant again. Well, wait, so why is grandmom upset about. She's already got a kid. He's already got a kid with this lady. When they told him about you.

[Jay Chandrasekar]

No, no, it was when they told him about my sister.

[Ryan Sickler]

Oh, got it.

[Jay Chandrasekar]

That was the issue.

[Ryan Sickler]

Got it.

[Jay Chandrasekar]

Yeah.

[Ryan Sickler]

You're just too bad. Now he's coming.

[Jay Chandrasekar]

When I came along, she was thrilled. And to be frank with you, is because I was a boy.

[Ryan Sickler]

Is that right?

[Jay Chandrasekar]

Yeah. This desire, it makes it sound like Indians are really, like, archaic, but in terms of this male error, it matters to them.

[Ryan Sickler]

We carry on the name.

[Jay Chandrasekar]

You know, I think that frankly, like, you know, at the time in India, you couldn't be a woman and really accomplish money outside the house in the same way men could. Now, obviously, my mother was a doctor, so things had changed. You know, India's had, you know, a leader that's a woman twice that they voted for. So there's.

[Ryan Sickler]

There are a lot of blows me away that other countries have had that we have not had one. It's wild.

[Jay Chandrasekar]

Yeah. But you know, back a second and.

[Ryan Sickler]

Ask about your mom. So you say in the 60s, I believe you said, they came here. So your mom early on is not only Indian, but she's a woman too, doing this. So she. Is she a big deal in the medical world back then, at least for who she is, what she's doing.

[Jay Chandrasekar]

Like, she was a very skilled radiologists. Like they. Like when Reagan came to town, they called her up and they said, are you a Democrat? And she goes, of course. And they said, if the president gets shot, will you take Care of him. And she said, of course, absolutely. And so she was one of the doctors on call in case, you know, in case something happened.

[Ryan Sickler]

I didn't know they did that.

[Jay Chandrasekar]

Oh, yeah, they, they would say that makes sense. Who are the best people in town? You know, we'll call them and make sure they're just available in case something happens. You know, it's interesting.

[Ryan Sickler]

You could be like, nah, I'm not gonna take care of that guy.

[Jay Chandrasekar]

You could really say, right, right, right, right, right, right. That's right. That's right. But, yeah, I mean, she came, when she came here, it was Chicago in The, in the 60s, right. So there was a, in addition to the civil rights movement, there was a massive women's rights movement. Right. And my dad was like, well, okay, we had the two kids, we did the thing here. Let's go back and live in India. She goes, I'm not going back there. And he goes, what do you, what do you mean? She goes, well, I'm not, I already. I have way more rights over here. She goes, I'm not going back there. She goes, you can go back if you want to, but we're staying here because I'm a, I'm more free here. More. I mean, yeah, I mean, look, Indian women have accomplished a ton over there. Like, I mentioned that prime minister, but, But I, I, I, I think it was just not as caught up as it is now. Like, it's apparently now a lot, a lot better. It's still not here, but it's on its way, you know.

[Ryan Sickler]

So what's it like growing up for you in Chicago, then? Are you. Like we talked before we recorded. You're the Indian family.

[Jay Chandrasekar]

Are you the only one? The only one for miles and miles and miles.

[Ryan Sickler]

There's no Indian community in the area.

[Jay Chandrasekar]

We were on the, we were on the sort of the vanguard of it, like, and we were living in Hinsdale, which is like a, you know, it's like a white suburb. Right. And, but, you know, I had two doctor parents, right? So where there was, no doubt, racism in the country and in the city of Chicago and the suburbs, sure, of course there was. Right. But we were coming in at a financial level that was confusing, I think, to people, you know, because we were skiing in Steamboat and we were going to England and France and whatever, and there were people who were like, these are their doctors and what? You know, so we were always treated with immense respect.

[Ryan Sickler]

Okay.

[Jay Chandrasekar]

You know, like, I don't. And it's why, when it comes to racism, if you Ask me, the story isn't the same as. As what I see in the news. And, and you know, it's not. It wasn't like, you know, the worst it got for me as a kid was my best friend. He had white. He was white, blonde hair. And he said, you're brown because your mom left you in the toaster too long. And I said, you're white because your mom didn't toast Right. And that was, that was, you know, it doesn't mean, it doesn't mean ball.

[Ryan Sickler]

Busting when you're kids.

[Jay Chandrasekar]

It doesn't mean people didn't say things privately about me. Who the fuck knows? I mean, people make. Used to make Indian jokes routinely, but I always kind of thought they were funny. Like, I was. I always played the Indian in Cowboys and Indians. Always. I never played the Cowboys.

[Ryan Sickler]

You're never a cowboy.

[Jay Chandrasekar]

Never. And we used to do that thing where you go. And my grandmother was like, stop. And I'm like, what? She goes, you know, that's the sound you make at an Indian funeral when someone dies. And I'm like, I can't even do the sound. And the, you know what a 10 people are like, you're a terrible Indian if you won't do the sound. Well, yeah, but I mean, I was trying to be.

[Ryan Sickler]

You never had an issue with friends, parents not want you to spend the night or any of that?

[Jay Chandrasekar]

Nothing.

[Ryan Sickler]

You were always welcome.

[Jay Chandrasekar]

Never, never. And I, you know, they were, you know, like, my friend's parents were like from Kansas and they just were like, fantastic. I mean, like, they, they. You remember racial language around black people, you'd hear it, right?

[Ryan Sickler]

Well, how old are you, Jay?

[Jay Chandrasekar]

57.

[Ryan Sickler]

Yeah, I'm 52. We grew up with truly tasteless jokes. Remember those books? And they're Polish, black. There were dead baby jokes. There's a whole section of. You couldn't even print that book today.

[Jay Chandrasekar]

Great books, great book.

[Ryan Sickler]

I used to sit in the bookstore and read those. And Far side I could just. The ladies like, are you going to buy this book? I'm like, nah, I'd sit there and read Far side and Truly Tasteless Joe. And there were volumes of them. Yeah, volumes.

[Jay Chandrasekar]

Yeah. Right. And so, you know, it was. But they were. Yeah, I was very, very accepted. And. But what the. The place where I would say it started to kind of. I had to pull off hooking up with white girls as not their ideal image of what, you know, because all girls in the country are fed Sean Cassidy. And they're fed Sean Cassidy, you know, like, you Know times at Ridgemont High they're fed a guy.

[Ryan Sickler]

Sure.

[Jay Chandrasekar]

And I'm not. I don't look like that guy. Right.

[Ryan Sickler]

And so does that work against your.

[Jay Chandrasekar]

For you worked against me. Okay. But I had to figure out how to do it. And it made me. Probably made me really lean into the funny because there was no doubt I was funny to them and charming to them and I was also the fastest guy in the neighborhood.

[Ryan Sickler]

Oh yeah.

[Jay Chandrasekar]

And. And at the time being fast meant being cool because you're picked first. And all the games. Capture the flag, smear the queer. We used to play. Yeah. And I was fast and so I was valuable. And you know the girls who would kind of hang around there like pretty fast. He's got a funny. And we would be drinking and I would manage to pull it off. You know, I managed to certainly pull it off. What I always felt was I didn't get the easy stuff. The one where I would be with like friends and some random hot girl would walk up to them and be like you're cute. And they, you know, they do that. And I'm like I never got that. I mean I did get it eventually but. But initially I didn't get that. And it bother. It bothered me a little bit that, that how hard I had to work for.

[Ryan Sickler]

Yeah.

[Jay Chandrasekar]

But you know, look, in the country's like origin, in the origin of this country it says we hold these truths to be self evident that all men are created equal. And I thought that was must be true. And so I'm like, I'm equal. Like it didn't. I mean it says so in the thing. Even though I know they didn't mean it for women or black people or brown people because then we weren't around. But had they thought about it properly they would have written it more explicitly. Luckily they didn't. It didn't even occur to them.

[Ryan Sickler]

Yeah.

[Jay Chandrasekar]

That some brown guy could come here and hook up with their white women.

[Ryan Sickler]

You never had an issue with that? Now that I think about it. No parents were problematic with you dating their white daughter.

[Jay Chandrasekar]

There was a like a Jewish girl who I dated in summer school and her dad to her called me the Bhopal Flash. The Bhopal Flash was enormous chemical explosion in India and blew up in like the mid-80s.

[Ryan Sickler]

This chemical Three Mile island here. Yeah, it's like a chemical and he's calling you that.

[Jay Chandrasekar]

And hundreds of Indians just vaporized. And he would. He as his joke he called me the Bhopal Flash. And he was like, he what? He really didn't want is his. Her daughter with like a non Jewish guy. And you know, look, the, the, the understanding of, of that culture and the need to procreate. I, I kind of get it.

[Ryan Sickler]

Yeah.

[Jay Chandrasekar]

But no, the answer is, you know, there have been. There were a couple girls I dated who were like, I probably shouldn't introduce you to my dad. And I get it and I don't care. And so what? Like, is that the worst I'm having.

[Ryan Sickler]

Yeah, yeah.

[Jay Chandrasekar]

I'm putting my penis inside of you is the worst. I don't mean to shake your. Is that the worst thing that's happening? Like, I'm like, everything's a little tough for every. Is that my crutch to bear? Okay, fine. My cross to bear. Right. Okay.

[Ryan Sickler]

So what. What point in your career or life. Excuse me. Do you decide to make comedy your career? And, and how is that met by two doctor parents?

[Jay Chandrasekar]

Well, I was, I was. I got. Made people laugh, my friends. Then I, I ended up in high school. I went to boarding school, Lake Forest Academy, where my sister was already a student. And I end up in this.

[Ryan Sickler]

What exactly are they teaching you in boarding school? What are they trying to. What. What's different about even a private, regular school?

[Jay Chandrasekar]

Well, you know, my mother had read a story about some black kids getting bullied in the public school, a grade school, and she's like, that's not going to be a good mental start if this happens to our kids. So she goes, we'll send you to the. The best private school in the area. And she always told me, you. What you do is you find out where the Jewish kids go, and that's where you send the kids. And now it's, you find out where the Indian kids go. And that's very simple. But whatever. So at the time, we were the only Indian kids in the school. And there was no bullying, like zero. No racial bullying, I can tell you that, because There are only 25 kids in the class. Yeah. So they're like, you're being watched. There's no chance, Right, that you could get away with it.

[Ryan Sickler]

And what's. Do you sleep there?

[Jay Chandrasekar]

No, no.

[Ryan Sickler]

Well, no.

[Jay Chandrasekar]

When I go to high school. Yeah. Yeah, high school.

[Ryan Sickler]

So you went boarding school all through.

[Jay Chandrasekar]

Just starting in high school.

[Ryan Sickler]

Oh, just starting high school.

[Jay Chandrasekar]

And my sister was already there. She really liked it. I didn't really want to go. I was like, let me go to the public school. I knew a bunch of kids who were going there, and my parents had gone to boarding school when they were 10 in India. British boarding schools. And I was like, they're like, just go for a year. See how you do. And so I did. And immediately I had this Japanese roommate from Japan named Shingo Suzuki. And I'm like, it's some least John Hughes thing. I'm gonna. I mean, can you believe it? And I'm also. I'm also in the minority dorm. And I'm like, listen, I'm like, I like Animal House, too. What am I doing?

[Ryan Sickler]

Yeah, why.

[Jay Chandrasekar]

Why am I in this dorm? The tiny dorm, the dorm they could keep an eye on so no one's getting bullied. And I'm like, fucking shit. And the kid, you know, Shingo, he didn't speak a word.

[Ryan Sickler]

None.

[Jay Chandrasekar]

And he had an older brother, Matsu, who was like three years older. The rumor was they both knew karate. And I know they're from Japan. I know karate's from another place, but okay, whatever. So Shingo gets a boil on his face. Like a real big thing. It's like a huge pimple, it looks like. And I'm like, I got a roommate with a boil, and he doesn't speak Japanese. And I'm just really annoyed with my situation quickly. And I come home to my room and it's locked. And I'm like, trying to get in with my key, but there's a body leaning up against the door. And I smell what I know has to be weed, right? I know it.

[Ryan Sickler]

And I'm like, smoked at that point.

[Jay Chandrasekar]

No, no, no. I thought it was for bad people. Me too. And I, you know, I drank. I mean, I drank already quite a bit by at the end of seventh grade and eighth grade. So I was hip in my view, but weed, I don't know. And the weed, if you. If you get caught with weed at that boarding school, one strike, you're out. Kicked out of school. Same with alcohol. And so I was like, oh, Shingo and this other dude down the hall are in there smoking weed. And they open the door and they look through the crack. They're like, we're busy. And I'm like, okay. So I go down the hall to my buddy's house and my buddy's room. They're like, there's not gonna wait in there. And he goes. And my. My friend's like, yeah, that's pretty bad. I'm like, you know, I could get kicked out if. If the people are like, hey, they're all smoking weed in there. They think I'm. So I tell on them and I tell the proctor, the whatever, the senior who lives on her hall. And he's like, well, that's. I'll talk to them. I'll take care of this. Meanwhile, I'm thinking I can get a new roommate, right? Because he's going to get kicked out. But now this guy's like, no, I'll take care of it. And I'm like, he's not going to take care of it. So I tell the vice principal, I go to the thing, and I'm like, he was smoking weed in there. Dude is kicked out of school, okay? So is the other guy. And everyone is like, you narc. And I'm like, I didn't do it. Of course I did do it. And. And I'm like, he's going back to Japan. Oh, yeah. No, he's going to military school in America. Can you imagine how rough that was for Shingo? Fucking shaved head. Oh, my God. Right?

[Ryan Sickler]

And he doesn't speak English, and he's about to go get yelled at. English from this far away, they're gonna scream, oh, my God.

[Jay Chandrasekar]

Kids in that school. My God. So now I'm the narc going through freshman year. And people like, this fucking narc. And I'm like, no, I'm cool. I want to hook up with Jackson. And. And so I'm having a kind of a hard landing. And my sister's like, why don't you get in the play? She goes, I'm in the play. I'm in the chorus. And I'm like, okay. She goes, you make tons of friends. I'm like, okay, play, whatever. So I auditioned for the play, and there's a huge chorus, and they don't even take me in the chorus. And I'm like.

[Ryan Sickler]

They say, no.

[Jay Chandrasekar]

You know, and that was the beginning. Your.

[Ryan Sickler]

Your badness will stand out.

[Jay Chandrasekar]

That was the beginning of my. Fuck you. I'm going to do it anyway. Okay, so the next play, I'm like, ninth grade. Yeah. Yeah. I'm like, I'm coming. Boom. And so I get cast in this next play, Brigadoon. I play a Scottish klansman. I've got a kilt on, and I sing a couple lines, and the teacher's like, you're pretty good. And I end up becoming the lead in all these plays, you know, eventually. Like, you know, Death of a Salesman, Kiss Me, Kate. A lot of singing and dancing and. And just regular acting, and I'm getting laughs in the place.

[Ryan Sickler]

Have you ever sang before in front of people?

[Jay Chandrasekar]

No, I was in the club.

[Ryan Sickler]

Did you know you could sing a little bit? Carry a tune?

[Jay Chandrasekar]

I played Tony in West side Story. Okay. That's how good I used to be.

[Ryan Sickler]

Okay.

[Jay Chandrasekar]

I can't do it anymore. And then I. I graduate to Colgate University, where I went to school, and I'm in all the plays. I'm getting laughs. I'm getting laughs. And I'm like, you know, I'm going to give this career a try. But first, instead of just taking what I've done here, I'm going to go to Chicago and I'm going to. I'm going to see if I can make strangers laugh. If I can make strangers laugh, I'll give this career a try. And so I go to Chicago. Like, I take a semester off and I study there, but I'm. And I get involved in the improv Olympic, and. And I'm in a, like, an improv group with, like, a mom, an accountant who wants to come out a little more. And, like, we were the worst improv group in Chicago, and we were getting zero laughs. Meanwhile, Chris Farley.

[Ryan Sickler]

So what, you had created an actual group?

[Jay Chandrasekar]

This was part of the improv Olympic. I was in classes with this guy, Del Close, who was the teacher. Chris Farley was in the class.

[Ryan Sickler]

Sharna.

[Jay Chandrasekar]

Sharna.

[Ryan Sickler]

I've heard that name so many times with all the people.

[Jay Chandrasekar]

Was in the clouds. These guys were the top comedy group. And my buddy James Grace was in that group, and they were killing. And then we would go up and it'd be crickets. And I'm like, this is not. This is not. I'm not. I haven't made anybody laugh. So I go. I write 10 minutes of stand up. I go do a standup show in Chicago, like an improv, whatever, open mic, and I get some laughs. And I'm like, okay, okay. I'm going to give this career a try at some point. And my dad is like, because they're. They're not. What? What do you mean you're going to give this career? My dad, you know, when I was applying to college, I had a B plus average in high school. And he's like. And I applied to all these Ivy League schools because I'm like, they're going to want me. And he goes. He goes, why would they want a junkie B plus Indian with all these good A plus Indians to choose from? And I was like, I mean, this dude was number one. Mom was number one. I'm like, they. And they were right. I didn't get into any of those schools. And so they were like, what do you. Are you out of your mind? There are no Indians on the screens. None except for Ben Kingsley. And, you know, the. They weren't going to make a Gandhi to the way that one ended.

[Ryan Sickler]

Right.

[Jay Chandrasekar]

I mean, there was no. There wasn't going to be another movie for me. Right. So I was like. I was like, okay. And then I remember telling my dad. I was talking to my dad about a movie, and it was. It was Short Circuit.

[Ryan Sickler]

I remember, because you have to.

[Jay Chandrasekar]

Spielberg? I don't think so. No, No, I don't think so.

[Ryan Sickler]

I remember the robots.

[Jay Chandrasekar]

It might be Short Circuit two. He goes, you have to see Short Circuit two. There's an Indian in it. And I said, dad, that's not an Indian. So it's a white guy in brownface. It's Fisher Stevens in brownface.

[Ryan Sickler]

Is that right?

[Jay Chandrasekar]

Yeah. And he goes, well, it's as close as we'll get. And I'm like, give me a few minutes. Give me a fucking few years. I'm going to make that happen. And then I decided, you know, somewhere along, you know, I'd started a comedy group at Colgate, which eventually became the comedy group I'm in now, Broken Lizard. And I was like, the only way I'm gonna get on the screen is if I write my own scripts and put an Indian in the middle of the movie, and then they'll have to cast me. And then I was like, they might cast somebody else, right? So I better direct this movie. Movie. So I learned how to direct, and then I directed and raised the money and produced it. And with a buddy of mine who really produced it, I just sort of raised money, and then I forced myself into the middle of the movie, shot the movie, got into Sundance, and people are like, oh, there's one. There's a real Indian right there. I'm the Jackie Robinson of Indian comedians. I mean, I am. You can ask Mindy Kaling. You can ask a zoo. He's on. Sorry. They'll all tell.

[Ryan Sickler]

They give you the nod.

[Jay Chandrasekar]

Absolutely.

[Ryan Sickler]

So did they try? Because I've had so many comedians, I've had the pitches myself. Josh Wolf is one of my favorite stories, where he pitched his show to NBC, the Josh Wolf Show. And they were like, yeah, yeah, yeah. And then at the end, they literally said, so who do you see playing Josh Wolf? And he was like, me. And they were like, yeah. Nah.

[Jay Chandrasekar]

Yeah.

[Ryan Sickler]

Did you get any of that?

[Jay Chandrasekar]

We got. You know, because we made this film, Puddle Cruiser, independently. It was like. We made it at. Shot at a Colgate after we graduated. We were in it, and then we tried to go Make Super Troopers. And we'd roll around town with a script, and nobody wanted to finance it because we were in it. And they were like, you know, this one guy is like, I'll give you the money, but Ben Affleck has to play that part. Thorny. And I'm like, that's my part. And he goes, not in this picture, kid. Nuh. And so we somehow managed at the last second, when we were basically about to break up, we got the money and made it. And we were. Then we sold it.

[Ryan Sickler]

And so we proved you did more than sold it. Created a. Yeah, we made it for a million two.

[Jay Chandrasekar]

And sold it for about three and a half. Right? Yeah. So we were making Hollywood money. And then they were like, okay, okay, you guys. You guys can actually be in the next one because you made a lot of money for us. And, you know, I forced my way in the door. Had I been a white actor, I would have never learned how to write. I would have never learned how to direct because I wouldn't have felt like I had to. It'd be like, that cute girl coming up to me like, you're cute. You want to make out? Like, that didn't happen to me. That wasn't going to happen for me in show business. I had to force my way in the door with, you know, whatever means necessary.

[Ryan Sickler]

And how hard has it been to stay in?

[Jay Chandrasekar]

Look, at the end of the day, it's incredibly hard to maintain a show business career because you're known for that one success. And they're like, we don't age anymore. But. And. And. But if you keep writing movies with your character, an Indian character in the middle, and people are like, they made money on the last one. And we keep. Now we're going to make our, you know, pretty soon, probably make our ninth movie, the next one. Python made four.

[Ryan Sickler]

Yeah.

[Jay Chandrasekar]

You know, like. And I'm not saying we're Python. We modeled ourselves. I mean, Monty Python, Broken Lizard. We named ourselves after them.

[Ryan Sickler]

Is that right?

[Jay Chandrasekar]

Yeah, we're trying to.

[Ryan Sickler]

Holy Grail.

[Jay Chandrasekar]

Yeah, we're trying to be them.

[Ryan Sickler]

So let me ask you this. I have a couple questions. I want to know who was more supportive at first, mom or dad. But also, I use this example all the time. They're doctors, you know, and I say all the time, you know what they call the person who finished last in med school? Doctor. But for a doctor, there's a very specific program. You do this, you do this, you go here, you do this, you do this, you become a doctor, you become A surgeon become whatever. For us, there's none of that, like, it's literally you. Someone can look at you and be like, this remind me of an ex, and I don't want to work with you. It can be that dumb sometimes here. So who was more supportive at first? And were they super resistant? Like. Like I'm saying, like, they're like, wait, what are you talking about? We're both top of our class, and if you just do A to Z, you become this.

[Jay Chandrasekar]

They thought they knew I was a little bit of an odd duck in terms of the Indian kid. They, you know, they knew I drank. They knew I was.

[Ryan Sickler]

Is that not typical?

[Jay Chandrasekar]

I drank it.

[Ryan Sickler]

I mean, for Indian kids.

[Jay Chandrasekar]

Got hammered in fifth grade. Did you? Yeah.

[Ryan Sickler]

What. Where the hell did you find.

[Jay Chandrasekar]

I went behind my dad's bar with my buddies. We. We put in, like, two inches of every single alcohol. Jesus in a pit. Tennis pitcher.

[Ryan Sickler]

Oh, you did it all in one.

[Jay Chandrasekar]

Picture and put ice in there? Shook it up, Walked around the neighborhood and drank it. Got absolutely blasted.

[Ryan Sickler]

Probably got fifth grade body with liquor.

[Jay Chandrasekar]

Yeah. And my friends rang the doorbell and ran home. I drank the most because I wanted to prove I'm that kid in the movies. And my mom is like. And, you know, she sat up with me all night. I was throwing up, and I was apparently calling her a. Right? And I know. And then the next day they took me to dinner, and I couldn't even look at the glass of wine on the next table. And they, you know, my parents are never big on punishment. They're like, that's your punishment. And I'm like, okay. And I didn't drink again for another two years. And then in seventh grade, by the way.

[Ryan Sickler]

Yeah, that's funny.

[Jay Chandrasekar]

Seventh grade, I started drinking and never stopped. Still never stopped. And, you know, they knew I probably was, you know, into weed, and they kind of knew I was probably into, at some point, to coke. And they would say stuff like, everything in moderation. And I'm like, everything.

[Ryan Sickler]

And your sister was more straight lady.

[Jay Chandrasekar]

A little more.

[Ryan Sickler]

Yeah.

[Jay Chandrasekar]

I mean, absolutely. I mean, she dropped acid in high school, but she was. She was, you know, she was like number three in her class.

[Ryan Sickler]

She was, too.

[Jay Chandrasekar]

Damn. Yeah. I mean, by the way, I was number seven. I was like, I was nothing. Right. But B plus, Right. And so. So she. She was. Went to law school and she was better. Yeah, she was just. It was impossible to say, like, objectively from a numbers perspective. She was right there. But they liked what I was. I was this rebellious guy.

[Ryan Sickler]

Okay.

[Jay Chandrasekar]

And they liked. And they knew I was like, to them, like, insanely cocky. They were like, how do you think you're gonna. Okay. You really think so? Okay. And that. But I would accomplish things. They'd go, okay, wow, you did that. So they were like, he's definitely gonna fail, but we're not gonna say that to him. We're gonna say, what are you gonna do in four years? We're gonna give you four years. What are you gonna do? And I said, I'll go to law school. They're like, okay, deal. And so they. I've talked to them. They're like, yeah, we knew you'd fail. We knew you'd fail and you'd go to law school. And that was good enough for us. Law school, Great. Fantastic. We wanted you to have a. You lived a certain life. We wanted you to have a life similar because, you know, the other life would be harder on you. And we are where you are. Right. Was right in your grasp. If you wanted it and if you're going to let it go, just make the deal. Four years, go to law school. And, you know, got into Sundance and they went there and they quickly.

[Ryan Sickler]

Was it in that four year window?

[Jay Chandrasekar]

No, it was seven years.

[Ryan Sickler]

Seven.

[Jay Chandrasekar]

You know, but. But we were doing shows in New York and we were selling them out and we were getting on little tiny things on Comedy Central and they were.

[Ryan Sickler]

Like, seeing enough progress that we're going to keep going.

[Jay Chandrasekar]

I mean, I can't believe you even did that.

[Ryan Sickler]

Right. They were like, tv.

[Jay Chandrasekar]

Yeah. You're on the. Yeah.

[Ryan Sickler]

Holy crap.

[Jay Chandrasekar]

And then we get into Sundance, they come and they're like. They see the crowds. Oh, my God. They're so. I mean, you know, and people. Because that. Your son, they're like, wow. And Indians love.

[Ryan Sickler]

You're all out there skiing. They're like, look at these guys.

[Jay Chandrasekar]

Indians. You know, the great thing about India is it makes the most movies of any culture in the entire planet.

[Ryan Sickler]

I wanted to mention that before. So Bollywood hadn't really popped off or any of this, like, coming over here. I mean, as far as our awareness here, you still are just before that. Then you're like Eric Estrada before the Latin boom hit, bro. You know, like when Jlo and Ricky Martin. Those guys got it right.

[Jay Chandrasekar]

Yeah, that's right. I mean, there were. No, the only Indians on screen at the time were Peter Sellers and the Party, bro.

[Ryan Sickler]

I'm ignorant as Peter Sellers is Indian.

[Jay Chandrasekar]

No, no, he played an Indian. Oh, okay. I was gonna say, watch a movie called the Party and it's a fucking great movie. And he's great, and he is, and I love him.

[Ryan Sickler]

It's why Panther is one of the.

[Jay Chandrasekar]

It's why I always say to my kids, not everything is racist.

[Ryan Sickler]

I'm glad to hear you say that.

[Jay Chandrasekar]

You know, like, there are things that are a little racial, but that's a little bit natural human behavior. Somebody cuts you off in your car, you notice their race. That's the first thing you notice. Or their sexuality or whatever. And you're like, you mother. You know, like, it's just reality. Right? And so not. Not everything is meant to be mean. You know, like racism. You know, there was the south, where there were shooting black people with hoses and unleashing dogs. And there was the Chicago suburbs where the girl was like, I don't know. You're not the. You don't look like Sean Cassidy. Like, one's racism and one's like, you know, preference.

[Ryan Sickler]

Right.

[Jay Chandrasekar]

Like, it's not. I don't know. I mean, ultimately, you know, the beauty of this country at the time was that there was a. If you made an independent film in the 90s with your friends, you made it cheap. Harvey Weinstein might buy it, put in 1400 screens, and boom, you're Ben Affleck. Right? Like, that was possible. And we. All we did is. We're like, well, let's take that system. We'll make a movie, plug it in.

[Ryan Sickler]

Dazed and confused, you got McConaughey, Parker Posey, Ben Affleck. That's. What's his name now. That's on Yellowstone. That guy's the. The rip guy is Dazed in the red hair.

[Jay Chandrasekar]

Yeah, yeah.

[Ryan Sickler]

It ended up launching, like, monsters. Monsters. Not just like, I've seen that guy. Monsters. And I'm sure I'm missing some that are in there, too. Jeremy London or one of those guys.

[Jay Chandrasekar]

That's right. That's right. I mean, it's a great movie. That's a great. McConaughey, you said, right? Yeah, yeah. I mean, so that was available to us. Sadly, it's not available now. Like, it's not the same. You know, like, now you make an independent film and. And Netflix buys it, does no advertising, and they're like, maybe somebody will watch it. And often some people do watch it, but it doesn't have the majesty and the magic and the movie star. I was on big, big screens in wide release, and people were like, that guy's a movie star. And really what they meant was, I started a movie. You know, movie stars. Another thing. But you know what I Mean, like, I was up there. And so they got used to it, and they're like, okay, I guess they can be up there. I guess we don't have to put Peter Sellers in brownface. But, you know, it was. It was. But, you know, to. To complain about the racism of Hollywood is a little. It's not that it's silly. It's a. Here's how it works. The majority of the writers, when I was coming up, and I mean, like, 99.9% were white.

[Ryan Sickler]

So they're writing stories mostly male as well.

[Jay Chandrasekar]

Yeah.

[Ryan Sickler]

Or do you have a mix of female in there?

[Jay Chandrasekar]

Mostly. Mostly male.

[Ryan Sickler]

Just curious.

[Jay Chandrasekar]

And they. It's not the case now, but they naturally are writing for the memories of their high school.

[Ryan Sickler]

Sure.

[Jay Chandrasekar]

When they were going to school a bunch of white kids, and they're trying to date the hot white girl or the hot white guy. And the Indian guy is the funny buddy, often with an accent. Long Duck Dong. Right, Right. That dude is funny as long as funny as. Right. But if I'm looking to get into a movie, I'm playing long Duck Dong. Like, that's how I'm getting in that movie. And when you play long Duck Dong, you. You're not gonna be the guy who eventually, you know, is Jennifer Aniston in some other movie, right? Yeah. That's not how that's gonna go down. And so you gotta like. I was like, I don't want to be long duck Dong. I want to be the guy who gets to Jennifer Aniston in the movie. So I'm gonna write myself into the middle of this movie as this guy who actually does hook up and see people go, this Indian guy can hook up. Okay. You know, it's just. It's. Eventually you realize it's sort of like. It's not mind control, but it's like conditioning. You're conditioning people to see you as the person you are. Like, listen to this voice. Like, where's it from? Right. And I'm a Chicago Bears fan. I mean, I've seen almost every single goddamn game since I was a kid. Is that how you think of Indians? No. No. I play golf every single day. I shot. I shot even par yesterday.

[Ryan Sickler]

Did you really?

[Jay Chandrasekar]

Yeah.

[Ryan Sickler]

Yeah, dude.

[Jay Chandrasekar]

Yeah. I mean, is that how you think of Indians? No. Right. And so, you know, the job of the people like me is to change the minds. You know, Irish used to be do not apply. The Italians used to be called all sorts of awful names. Now they're all the ones in Trump's party. Try to Exclude the new guys. Right? Indians, you know, in, in 20, 30 years, like we're hoping to be in that Republican party, excluding all the new guys. That's what we want.

[Ryan Sickler]

So once I'm off, whatever, okay, politics could have at it. I, once you do that, once you accomplish this and your parents see you up there, are they just blown away because now you're, you're doing something nobody's ever even done before. Is it something that, you know, you look back on fondly later and realize what you did, or are you feeling it in the moment? You know, do you know what's happening?

[Jay Chandrasekar]

I'm not feeling it at the moment because as far as I'm concerned, I'm an American dude in a comedy movie. And I'm like, well, that's what I wanted it to be and that's what I am. And it worked amazingly. And you know, I, I always say the country is very big hearted, that it was like, sure, great, fine, that's funny. Funny's funny, right? The country is open minded enough to go, yeah, this guy. Sure, yeah, it worked. Hilarious.

[Ryan Sickler]

Listen, I've always felt that about comedy.

[Jay Chandrasekar]

Yeah.

[Ryan Sickler]

I feel like if it's funny, people go with it. Yeah, I understand. Drama, whatever, whatever. But if it's funny, I don't think people give a, what race you are, what sex you are, what you're wearing, none of it. If it's just funny, then I think people resonate and relate to that.

[Jay Chandrasekar]

Yes, I agree 100. I agree 100. And, and my parents were like, you know, they couldn't really deny it because I was continuing to make films and.

[Ryan Sickler]

And a living at it and a living not bumming money from them, I'm assuming.

[Jay Chandrasekar]

No, you know.

[Ryan Sickler]

Right, right.

[Jay Chandrasekar]

And so they were kind of like, wow. And they told me then like, we, we thought you were going to fail.

[Ryan Sickler]

Of course they did. But I mean, that's what success ultimately is, is a bunch of failures. If you stay in it long enough, you learn and you grow and boom, you finally get one.

[Jay Chandrasekar]

I always say show business is like a tiny island of success in a vast ocean of rejection.

[Ryan Sickler]

Oh yeah, you're not wrong about that. You get way more no's and, and.

[Jay Chandrasekar]

You have to be tough about it. Right. And that's like that guy Wolf, you know, he has to be, you have to say, okay, you said no to me, but I'm going to figure out a way somehow.

[Ryan Sickler]

Has there ever been a project where you were like, yeah, this one, this one. And it got a lot of momentum and then Just. No, there have been something where you were like, man, that one I wish we could have. Or maybe you're still trying with it.

[Jay Chandrasekar]

I never in my mind give up. Like, I never go, oh, we lost. Not going to happen. I always am. Like, I'm going to go hide in the bushes for a while, and I'm going to pounce when my moment happens. I mean, it's the behind the scenes of show business is about crafty people who are like, you know, I'm not going to take out this script now because I can feel I'm a little colder than I would. But when this other movie gets announced, I'm going to attack. And you're trying to constantly, you know, force the person with the money to go, this might be a good bet, and he's going to make money with somebody else if he doesn't make money. I should. I should, you know, like. Because if they make the wrong decisions enough, they get fired. And if they make a right decision and they make some money, they're like, hey, look who's the genius? It's. It's hard for them and it's hard, but you got to be reasonable and crafty about. About when to attack. And look, you know, I have directed, I think, 10 films.

[Ryan Sickler]

Is that right?

[Jay Chandrasekar]

And with Broken Lizard, It'll be like eight or nine with Broken Lizard, but maybe 11. Okay, 11 films. But you have to be crafty about it. There have been times that I've been cold, you know, but you can't be. I'm so sad.

[Ryan Sickler]

But you've also. You're directing and putting yourself in the film.

[Jay Chandrasekar]

Yeah.

[Ryan Sickler]

So you're shattering two stereotypes and. And crack. Well, maybe not shattering, but you're the tipping point for not only Indian directors, but also actors. And you're doing both of them in this one film.

[Jay Chandrasekar]

Because I have to. Because the. Like I was saying, the writers who are writing, they're all writing for white people because that's what they naturally do. Right. They're not like, hey, I'm gonna put this in a fictitious Indian guy I know nothing about into the center of this movie. So the opportunities for me as an actor were almost zero, unless I want to play the long Duck Dong character.

[Ryan Sickler]

What was less for you? What was directing or acting role?

[Jay Chandrasekar]

Oh, acting. Directing, sure.

[Ryan Sickler]

They don't give a shit.

[Jay Chandrasekar]

Who gives you behind the camera? Who cares? But acting, they're like, you know, look at all the people came out of Daisy confused. Like, they all acted in other people's.

[Ryan Sickler]

Less so for me, all white People.

[Jay Chandrasekar]

Well, okay. Yeah, because. Because they have all. There are all these opportunities, right? And you can go, oh, that's racist. Okay. I suppose.

[Ryan Sickler]

I don't mean it like that. I just mean you also don't have. You're also Indian, so you've got even a harder.

[Jay Chandrasekar]

Right. Yeah, I don't see it as racist. I just see it as a natural way that people write. When I write, I write an Indian in almost everything I do because I'm writing for me. So it's just. It's the. It's the story of what the writers. Changing the color of the writers in the. In the television rooms and the phone rooms. That's the key to changing the people on the screen. Because those. You know, you get a kid from whatever Harlem writing in a room like, New Girl, and they're like, we should have. This character is a really funny guy who happens to be black who was in my neighborhood, and they go, okay, let's cast this guy. And suddenly there's a guy on screen who's fleshed out. And, you know, there was a time where people were like, we have to have more black stories. Right? And they only had all these white writers, and so all these white writers were writing black stories, right? And you're like, okay. And then they would send it to me. They're like, you're kind of black to direct it. You're kind of kind. No, no, kidding me. I mean, the. Kind of. The amount of times I've been like. People said no, but they mean it.

[Ryan Sickler]

Yeah.

[Jay Chandrasekar]

Can you jump on this job? Because we got two white writers kind of about a black thing, and, well, you're a good face to bring in, and you make good stuff, and, you know. And then, you know, you're like, you know, you're along for the ride, but who gives a shit? Like, I'll make something great, and so be it. I mean, it's like they. I. Hollywood, had. They had a choice about me, they would have said direct. More like, look, I made the Dukes of Hazzard. Right.

[Ryan Sickler]

I know.

[Jay Chandrasekar]

I mean, that movie made $180 million. And there was. It was Knoxville and Shelly Scott and.

[Ryan Sickler]

Willie and Burke and the general lead for sake.

[Jay Chandrasekar]

Right. I mean, that is the other side of what my career would have been if I didn't act.

[Ryan Sickler]

Did you grow up watching that show?

[Jay Chandrasekar]

I loved it.

[Ryan Sickler]

Oh, my God. I had a wet dream.

[Jay Chandrasekar]

I had Daisy Duke on my wall.

[Ryan Sickler]

Did you get in the General Lee at all?

[Jay Chandrasekar]

Yeah, yeah, I drove that thing. We were on the. We were jumping the generally into 55 miles an hour of traffic on the 10 in New Orleans. And so what happened was we put.

[Ryan Sickler]

I want to hear this.

[Jay Chandrasekar]

Put the car on a hydraulic lift. And I say, we. It wasn't me. It was. Dan Bradley was the second unit stunt guy. He's. He's a killer. And I was there that day and I was driving in one of the cars because I'm like, I want to watch the General League. And we learned he launched it into the air and it landed in the space between all the other cars. There were cameramen in different cars and it landed. And the front axle always broke on the. Generally when you. When you jumped it and would slam it into a car, it was incredible. And I was standing on the 10 Freeway and the chief of police, you know, walks up to me and he goes, hey, son, I'm chief police New Orleans. I was like, oh, how you doing? He goes, you get in any trouble down here, you give me a call. And he gives me the card. He goes, anything short of murder? Anything short of murder. And then he paused. He goes, actually, for you, murder's okay too. Yeah. And you got the general lead jumping on his freeways. Dude, that is awesome. And then he's like, he goes, he goes, you gonna drive this thing? And I'm like, I. I mean, I'd like to. And he gets his calls, his police guys over. He goes, you get this guy an escort. And so we're flying on the 10 with a police car in front of.

[Ryan Sickler]

Behind and the general.

[Jay Chandrasekar]

You can't really get it much faster than about 90 before. It's like, yeah, it was incredible.

[Ryan Sickler]

I just the other night I sat and watched like a 20 minute smash cut of every generally jump from the show. Someone put it together on YouTube. It's just jump after jump. And I'm like, yes.

[Jay Chandrasekar]

Yeah.

[Ryan Sickler]

Yeah, that's fucking great.

[Jay Chandrasekar]

Back then there were guys in those cars. When we were doing it, we did some smaller jumps with guys in the cars, but, you know.

[Ryan Sickler]

So wait, when you say he launched his car, there's no driver? 1. There were any drivers in any of the.

[Jay Chandrasekar]

Some of them. Okay, some of them.

[Ryan Sickler]

But how many cars, how many general leads did you guys have?

[Jay Chandrasekar]

Well, movie on the weekend, it got green lit. You could get a. A Dodge Charger for about, you know, used one for about two. 2,000. Two.

[Ryan Sickler]

Two to 69.

[Jay Chandrasekar]

Yeah, like two to 4,000. Like it would if it wasn't mint. Like, sure. Pretty good.

[Ryan Sickler]

That needed to be redone.

[Jay Chandrasekar]

Four grand maybe, right? The word started spreading that the Dukes. And by the end of that weekend, they were going for 10, 15. We got. We took 25 Generales down to Baton Rouge and we had a. And we bought 50 police cars from Chris Nolan after his Batman. And we had all those cars sent down there. We had a 24 hour garage running. And so we. They would crash the cars in the daytime and they'd send them in at night. They'd bang out what they could and take parts and fix them up and then send them back out to those guys in the daytime. And we left town with one working mint condition generally, which is in the Warner Brothers Museum, which they probably don't display because of the roof.

[Ryan Sickler]

I don't know, maybe I just bought a generally shirt. I looked for one that didn't prominently display the roof. I got me a nice sigh one just of the O1 and looks good out there.

[Jay Chandrasekar]

You know, they offered me.

[Ryan Sickler]

You have one.

[Jay Chandrasekar]

They offered me a generally. And I was like. I said, guys, I live in Hollywood, you know, like, listen, I love what the car stands for.

[Ryan Sickler]

The show.

[Jay Chandrasekar]

That roof's a prop problem. You know, they. I don't know.

[Ryan Sickler]

I'd take that.

[Jay Chandrasekar]

They called me before we shot and they're like, we gotta take the flag off the roof. And I said, brother, I got a list of other guys who want to direct this movie and I will bring them in, I will prep them, I'll give them all my notes, but there's no way this Indian's gonna be the guy who takes the general. The roof up, man.

[Ryan Sickler]

Thought about that.

[Jay Chandrasekar]

I said, it's alone enough that I'm doing this, and there got to be some good old boys who are like, what the fuck? But I'm not going to be the fucking guy.

[Ryan Sickler]

What, they want to change it to an American flag or something? You didn't even get that probably.

[Jay Chandrasekar]

And I am like. They're like, well, I don't. Well, I mean, are you. What? They didn't.

[Ryan Sickler]

Isn't it funny to you because you said about racism and stuff like these, there's people like, we got to take the flag off the car. You rerun the show. The show. I could go watch the show online, on air right now. And you didn't take the flag off and that. Why the fuck do we got to do it now?

[Jay Chandrasekar]

I don't know. And Knoxville.

[Ryan Sickler]

Good for you.

[Jay Chandrasekar]

For Knoxville called me and he goes, I'm out. And I'm like, what? He goes, they're taking the flag off the roof. I'm like, they're not Taking the flag off the roof because I'm out. And then when they found out we were both out, they're like, fine, keep the fucking flag. I mean, but you're. You guys. They want to keep the flag on. And so we ended up in the opening of the movie. There's no flag on that roof. Right?

[Ryan Sickler]

I got to go back and watch it.

[Jay Chandrasekar]

Is that right in the opening? And it's a crashed up, beat up Dodge Charger. And they. They get. They. The Duke boys smash it up and it's all destroyed, and they get the car towed to Cooters, okay? Played by Dave Keckner and. And Cooter mints that thing out. He paints it orange. He gets everything perfect. And they. And they are getting chased by the cops at Dukes, and they sneak into Cooters, and they break out of Cooters, crash out. The cops are chasing. They get away, and they end up in Atlanta. And they're on their way to Atlanta to go check some coal samples, and they're in traffic in Atlanta, and people are like honking horns and go, all right, Rebel Yale. And they're like, all right, brother. And. And people. And then other people are like, fuck you. And they're like, what? What? What? What? And eventually they get out of the car and they realize that Cooter's painted the Confederate flag on the roof. And then they grow through a real black part of. Of Atlanta, and they're stopping at a sign and all these black dudes, what the. You know, and we just dealt with it in a modern way, and it was on the roof the rest of the way.

[Ryan Sickler]

That's smart.

[Jay Chandrasekar]

I mean, you know, I get it, I get. I get it. But it's called the General. A. It's literally called.

[Ryan Sickler]

It's called the General. Yeah. Dude, thank you for doing this. This is a great episode.

[Jay Chandrasekar]

Okay, that's fun.

[Ryan Sickler]

Before we wrap up here, I'd like to hear advice you'd give to 16 year old Jay.

[Jay Chandrasekar]

I would say to 16 year old Jay to treat the guys from Entourage with respect.

[Ryan Sickler]

What happened? Wait.

[Jay Chandrasekar]

What?

[Ryan Sickler]

Wait, I can't let you go out on that.

[Jay Chandrasekar]

I was. What the hell happened? I was. I was living in Hollywood. I'd made a couple movies. I was going to all the parties. I was hooking up with hot actresses. I was, like, living it, right? Not to the level that Mark Wahlberg lived it. Okay, I know, I know. But I had a little mini version of it, so. And I'm shooting television. I'm, like, directing Arrested Development, and I'm like, all these real people are like, this guy? And so I get a call, my agents, like, there's a television show, hbo, it's called Entourage. Take a look. They want you to direct. I'm like, they're big Super Troopers fans. I'm like, okay, whatever. I watch it. I'm like, nah, this is. This is junk. And so I call my agent. I'm like, I'm not doing that show. I'm like, it's nothing like it. I'm like, I'm living it. It's not like that. This is. These guys are not. This is dorky. This is not working. No. And he calls me back. He goes, I told him you were going to come in. And I'm like, why? I don't want to fucking do the show. He goes, it's hbo, dude. You can go.

[Advertisement Voice]

Go.

[Jay Chandrasekar]

Go in there, get the fucking job. Make it better. And I'm like, okay, I'll go in. So meanwhile, we're pitching with the great Larry Charles, right? Larry Charles. He directed Borat. You know, he's was on. He was one of the head guys on Seinfeld. He was eventually on Curb. Larry Charles is like, wow. So now Larry Charles wants to direct the new Cheech and Chong movie. And he wants. And we, Broken Lizard, come up with a pitch for this idea, and it's a whole Cheech and Chong movie. We come up with a whole pitch. We pitched Larry. He goes, I love it. And. And we were like, oh, we're gonna write it together. And Larry's like, I can't write with five guys. Just let me have it. I'll buy it from you guys, and I'll write. I'm like, you're Larry Charles. You can have the goddamn thing. Fine. But we got to know Larry Charles. And we're like, this is cool. We know Larry Charles. So I walk in this Entourage at hbo, and there's Larry Charles sitting there. He's fucking on Entourage, too. And he's sitting with these two guys. And, you know, I don't know these guys, but I know they made this show. And I spend I has to be 30 minutes talking to Larry Charles, ignoring those dudes about Cheech and Chong and da da da and Seinfeld. And we're laughing, da, da, da. Eventually, one of these guys, I think it was Doug, goes, so, what'd you think of the show? And I'm like. I said, well, look. I mean, I think it's a miss. I think you. I said, I'm living a version of this life. And it's, you know, it's a lot more fun. It's a lot funnier than. It's just different. It's more. It's just different. Okay. It's funnier and it's more irreverent. And you know, it. I think it's a mess. And they were like, they've been told I'm coming in to want to direct their show. And they're like, because they were lied to by the agent. Of course. Of course. Of course. Why the hell is elsewhere? And I'm like, all right, well, good to know you. And I'm like, assuming I don't know anything about enough about television that it's not going to go. And then I'm driving down Sunset and I see these Entourage billboards. I'm like, what the fuck? Why would they make this terrible show? And so I watch the first episode. I'm like, yeah, they did it again. It's the same show. It's terrible. Then they watch the second one. I'm like, it's a little more irreverent. So. And what you heard when I'm like, yeah, it's pretty good. And now I've become the biggest Entourage fan in Hollywood. I'm like, this show is fantastic, and it's on hbo. I'm like, that's pretty good. And there are all these hot girls in it. I'm like, I like it a lot. And so I'm sending word. I'm like, hey, I'd like to direct this show. And they're icing me. Nobody will. Nobody. And so I end up working with almost every single actor on that show.

[Ryan Sickler]

Oh, yeah.

[Jay Chandrasekar]

And I'm like, you tell Doug that I'm real big fan of the show. And. And they're always like, yeah, yeah, well, you should direct the show. And I'm like, yeah, I should. And. And one by one, they're said. They. They're all told, yeah, your meeting didn't go so well. Had I done that show, I'm sure I would have directed Game of Thrones eventually. I'm sure I would have been. And I'm like, the lesson is, don't be an asshole. Just. They're trying something creative. The pilots are always hard. Be open minded. But what were you going for? I see what you're going for. We can make it better this way.

[Ryan Sickler]

And that was really another thing your agent said is make it better. And that's fucking great. That's great advice. Yeah, it might suck. You might think it sucked. Get in there. Make it better. Then.

[Jay Chandrasekar]

That's right.

[Ryan Sickler]

Great episode. Thank you very much, man. Please promote everything you'd like one more time.

[Jay Chandrasekar]

August 8th, 7th, 8th and 9th, I'm at the Alamo Drafthouse in Arlington, Virginia. And get my app. Yeah, vouch Vault and vouch for all the things you love. Follow me. I'll follow you back. And I have a podcast called Mustache tales with Hayes McCarthy there.

[Ryan Sickler]

Great. Thank you very much.

[Jay Chandrasekar]

Thank you.

[Ryan Sickler]

As always, Ryan Sickler, on all your social media. We'll talk to you all next week.