Once upon a time a boy named Kalpen Modi went to see Indiana Jones and the Temple of Doom. Then, when he went to school, he noticed that the other kids didn’t want to sit next to him during lunch. “They were convinced I had monkey brains in my lunch box,” he says. It was a crash course in both the power of media and racial stereotypes, probably a little more than a New Jersey schoolboy could digest at that time. Now older and surer of himself, with upcoming roles in Superman Returns and The Namesake, and currently co-starring in A Lot Like Love, Kal Penn finally has the box-office clout to insist that he doesn’t want his roles served up with a side of monkey brains.

The man, after all, is a good vegetarian Gujarati boy from New Jersey. Even those White Castle burgers in his landmark movie Harold and Kumar Go to White Castle were actually soy burgers. “I said I’d be okay taking a bit of the beef burger and using the spit bucket,” says Penn. “But they said, wouldn’t you rather not have to put it in your mouth?”

The beef burgers were fake, the dope was some noxious non-marijuana herb that produced smoke that looked like pot smoke. But not everything was make-believe.

That was real Kal Penn butt in the nude scene at the beginning of the movie. “I had a roommate who did things like that,” says Penn. “So it didn’t seem unreal.” Penn sent the script of Harold and Kumar to his parents like he does with all his roles. “I am sure my mom would prefer I didn’t have to do things like that,” says Penn. “But I believe what she said was, ‘I know what you kids do.’”

His parents moved to the United States as part of the post-1965 immigration boom. His father is an engineer, his mother, who has a master’s in chemistry, worked as a fragrance evaluator for a perfume company. Penn and his younger brother grew up on the usual suburban American kid diet of movies like Karate Kid and The Goonies.

At that time there was little South Asian representation on screen. The family was not religious about Bollywood either. That was just the way it was for Penn as a kid. But looking back, he says, it had an effect.

“I remember seeing Short Circuit, where there was a white guy in brown makeup,” recalls Penn. And there was of course, Indiana Jones and the monkey brains. “The images, positive or negative are embedded in your mind,” says Penn. Luckily, a positive image came along soon in the shape of Mira Nair’s Mississippi Masala.

“It was incredibly empowering to see ourselves represented on the screen in a realistic way,” says Penn. “Even better, it didn’t hit you over the head with identity politics.” Now Penn gets to work with Nair as she films Jhumpa Lahiri’s The Namesake. “Harold and Kumar Go to White Castle was a hit and all the 13-year-olds in America know and love him,” Nair told the media. “(But) Namesake will be his first dramatic role.”

Penn plays Gogol, an Indian-American son of immigrant parents growing up, like him, on the East Coast.

But there’s another parallel. In The Namesake, Gogol struggles to define himself by changing his name to Nikhil. Penn also has what he calls “a similar name thing.” Friends and family still know him as Kalpen Modi, and that’s the name he prefers. As a struggling actor, he resolutely refused to Anglicize his name. But then when friends and colleagues kept pressing him, he changed it to Kal Penn almost as a prank. After all, he figured, the headshot was still a dead giveaway.

But the difference was electric. Auditions went up 50 percent. “I still haven’t figured out why a name made that much difference when the photograph was right there,” says Penn. “Maybe it signifies something to the person reading the name.”

But what gives someone with a name like Kalpen Modi the courage to try and make it in Hollywood? It was, says Penn, the power of acting, plain and simple. When he was in 8th grade he was in a school production of the musical, The Wiz. “It definitely wasn’t the cool thing to be in the drama club in 8th grade,” laughs Penn. He remembers being on the bus every day after rehearsal with the soccer players who would tease them. Then one day they performed some of the scenes in front of the school. “We were all terrified we would be made fun of on the way home,” recalls Penn. “And everyone just started applauding.” Penn suddenly saw how art could actually change people’s minds.

That change, however, doesn’t come easy. Like most of his generation, Penn was being groomed to go into a respectable profession like engineering or medicine. When he decided to become an actor, a well-meaning aunt even asked, “Are you not smart enough to go to medical school?” Penn bears her no rancor. “It’s based on a fear of knowing we moved here to start a life and we know what we are up against,” says Penn.

What surprised him were the reactions of his peers. He remembers going up to the Indian Students Association at UCLA, all excited about meeting fellow young desis.

Indian Student Association: What’s your major?
Penn: Theater.
ISA (laughs uproariously)
Penn: Ha, ha. No, but I am serious.
ISA (laughs even more)
Penn: You guys, I really am a theater major.
ISA goes very quiet. Then turns to the person behind Penn and introduces themselves.

“It was that blatant,” says Penn disbelievingly. Of course, while Penn was still in UCLA, he ended up in the campus indie hit American Desi. Then some of the same people in the students association were all over each other trying to invite him to their functions.

American Desi introduced Penn to a whole generation of college-going Indian Americans who had never really seen themselves on screen, with or without Apu accents. Penn actually auditioned for a different role—Salim. But then director Piyush Dinkar Pandya asked him to read the role of Ajay. “After a couple of minutes, Kal came back and asked me if the character of Ajay was like one of those desi thugs from Passaic, N.J,” recalls Pandya. “I knew instantly that Kal knew the type of person I was trying to portray.”

What Pandya noticed also was Penn’s gift for improv. He not only came up with funny material on the sets but, says Pandya, “he was equally funny off camera, keeping the cast and crew in stitches.”

The sense of humor has stood Penn in good stead. As a brown-skinned actor trying to break into an entertainment world where roles are few and competition fierce, Penn has needed both his sense of humor, diplomacy, and a bit of a thick skin.

After all, his first breakthrough national cameo, a single line on the Steve Harvey Show, ended up on the cutting room floor. “And they didn’t even tell me,” says Penn. “I was 19 or 20 and it was incredibly disappointing. I thought I could show all the aunties and uncles I wasn’t crazy.”

But he stuck it out and learned to navigate the system even when it came up with something like National Lampoon’s Van Wilder. Penn almost chucked that role. It wasn’t quite monkey brains but almost as stereotypical. Here is how Penn recalls his conversation with his agent.

Agent: There is a movie you need to go in for.
Penn: Okay. Who’s the character?
Agent: You won’t like the name.
Penn: Oh God, what is it?
Agent: You have to go in, okay?
Penn: Fine, I’ll go in. What is it?
Agent: Taj Mahal.

Penn (shrieks): You are kidding me. I am not going in. (Utters a bunch of profanities before hanging up the phone.)

But Penn calmed down and went in for the audition while his agent reassured him that auditioning was more about meeting casting directors than actually playing a role. When Penn actually got the role and saw the script, he realized it was as stereotypical as he had feared but it was also a character that actually advanced the plot of the film, not just a 2-3 line part. And this was a mainstream movie that would look good on his resume. “As an ethnic actor you have to work a million times harder than anyone else just to get your foot in the door,” says Penn soberly. “We have to be incredibly overqualified for even the smallest part.” He talked to industry peers and friends.

What helped him most was a friend who asked him how many things he found offensive in the script. Penn said there were probably about 30. She said, “You can’t pick all 30 because then it becomes a political issue. Pick 12 things that are so outrageous that you won’t be able to sleep at night if you say them. And then come up with something funnier.”

Penn did that and the gamble paid off. When Harold and Kumar hit the screen, the tongue-in-cheek promo described him as “that Indian guy from Van Wilder” and co-star John Cho as that “Asian guy from American Pie.”

But despite that success, Penn was very wary when he originally met the creators of Harold and Kumar, both of whom are white. The first thing he asked them was, “How thick are these guys’ accents?” When they told him Harold and Kumar didn’t have accents, he just laughed and said, “Good luck getting it made.” He never imagined a studio would pick up a teen film with South Asian and East Asian leads. At best, he thought, he could perhaps persuade some South Asian venture capitalist looking for a tax shelter to finance the film as a small indie film. “I could have shot myself in the foot,” he says reflectively. “I was jaded without realizing it.”

Part of that jadedness came from a deepening realization that despite a fascination with “Bollywood, samosas, and chai, the word American still has the connotation of white and wealthy.” Penn thinks it’s no accident that Asian films like Farewell My Concubine or a martial arts epic from China come into the American mainstream long before an Asian American one like Better Luck Tomorrow or Harold and Kumar. “It’s the commodification of culture, the notion of othering,” says Penn. “It’s the difference between acceptance and exotification.” And he goes into his pet peeve.

“I just go nuts every time I am in a coffee shop and someone walks up and says, ‘Can I get a chai tea latte?’ Lady, do you know how redundant that is—chai and tea—and there’s already milk in the chai, so what’s a chai tea latte? You just know she is going to do yoga and watch a foreign film she rented.”

But then he calms down and says perhaps that’s changing, thanks to a new generation, the kind that went to see Harold and Kumar, the kind who would not go to see an “Asian-American art film.” The success of Harold and Kumar is already spawning talk of a sequel set in Amsterdam. “A script exists,” acknowledges Penn. “It now depends on the DVD sales whether or not it gets the green light. So I implore everybody to stop downloading it and go and get a copy of the DVD.”

There are other projects in the works. While the David Schwimmer-helmed television series Nevermind Nirvana never made it beyond a pilot, Penn is co-starring with Ashton Kutcher in A Lot Like Love. Upcoming projects include The Namesake as well as playing one of Lex Luthor’s henchmen in Superman, a role he is excited about though he hasn’t seen the script yet. “Superman, it’s the quintessential American film,” he says.

That’s a long way to go for a boy from Montclair, N.J. Or perhaps it’s not. After all, as Penn keeps pointing out, no matter how others saw him, he never thought of himself “as trapped between being Indian and American.” He was always just the quintessential American kid who watched Karate Kid with his friends but just happened to speak Gujarati at home.

And Kalpen Modi asserts that unapologetic Americanness everywhere he can, including airports.

“I was flying back from Nevada,” Penn recalls. “I was with two white guys. We are all the same age, all on the same flight, all on the same kind of ticket, all dressed casually, traveling together with our backpacks and two of them are in front of me. They go ahead. And the guy stops me.”

Airport Security: Step over.

Penn: Why? (I think I was channeling my grandparents, who were in India’s independence movement.)

AS: Step over the side.

Penn: Why? (Damn. I am not going to be able to get onto the plane, am I? But I already started this.)

AS: Step over the side, sir.
Penn: Why?
(Repeat exchange for 30 seconds more.)
Penn: Why do you need me to step over the side?
AS: You need to be searched.
Penn: Why?
AS: Uh huh. Because your shirts are too baggy.

“I was like, really, that’s all you got?” says Penn. “I think it’s completely ridiculous. It does happen. It is racial profiling and it’s also scapegoating. Though these days the security guy at the end of the line might be younger. And so when I am usually through with the search, he’ll say, ‘Hey man, aren’t you the guy from …?’ And you know what? If you are the guy from TSA, and you are reading this, I am just not in the mood.”

Sandip Roy-Chowdhury is on the editorial board of India Currents and host of UpFront, a newsmagazine show on KALW 91.7 produced by New California Media.