400 pages later, and Kal Penn remains largely an enigma. His 2021 autobiography, “You Can’t Be Serious,” waffles smoothly from lewd humor at New Jersey Bar Mitzvahs to the mean streets of Hollywood, then downplays a breathtaking transition into an incredible side hustle as White House liaison to Asian American and Pacific Islander communities. Despite recounting lengthy, explicit wit-fueled dialogues from the elementary school playground and a long conversation with a female stripper, Penn glosses over a “hobby” degree in international security from Stanford and his journey homosexuality. It is a strange book, waffling between ego and despair, triumph and not-so-tacit inadequacy.
Yet even in 2021, one family features three times in a book about a 44-year-old’s journey to self: filmmaker Mira Nair, and her son, now-Mayoral Candidate Zohran Mamdani.
Kal Penn, born Kalpen Suresh Modi, switches from acting out in math (literally) to film with Mississippi Masala by Mira Nair. He first saw the film in the theater with his parents and a cousin in February 1992 after hearing about it through his Indian community in Edison, New Jersey. The fifteen-year-old closeted virgin was “mesmerized” by the interracial love story with a smoldering young Denzel Washington and “relatable” Indian immigrant family.
“None of Mira Nair’s characters was one-note,” he wrote. “They were all wonderfully flawed…I was in the front seat of an emotional rollercoaster.
He was changed forever.
“I walked out of the theater, heart full,” he continued. “…This was what images could make people feel on a larger scale if down creatively, inclusively, and in a not-lazy way. This was magic.”
Nothing else in Kalpen’s real life was magic. The actor went on to recall a rejection from Yale so painful he shaved his head, turning down an incredible, albeit unpaid, internship because he didn’t have a car, and disappointing his extended South Asian network with his unrelenting passion for the arts. He later apparently only eeked out a living with his most famous films. But Nair provided a release from the agony and self-loathing–rather, she validated the person Kalpen believed he could be.
“If Mira Nair and Sarita Choudhury can do this, maybe I can, too,” he said to himself walking out of the theater. “That day changed my life because it was the first time I watched something and saw myself depicted as a human being.”
Simply knowing “who Mira Nair was” incentived Penn to follow his dreams and apply to drama school.
He managed to tell her this in person as a student at UCLA. She was giving a talk, and although his raised hand was ignored, he pushed his headshot to her as she walked out the door. She did not reach out.
Life as a maybe-gay brown actor in the early 2000s was no picnic. Rampant racism and homophobia more than proliferate the film industry, they engulfed it. Penn, who learned discretion from his playground days, watched in mostly-silent horror as he witnessed brownface from other actors, and an expectation of “minstrelsy” with caricatured bug eyes and awkward performative accent. Yet, as he tells the reader in the first pages of his book, Penn is brilliant, and managed to dominated the frat boy bully culture that kept him down. His big break was in the 2004 cult classic Harold and Kumar Go To White Castle, about a Chinese- and Indian-American teen who get high and embark on fast food-motivated hijinks. Through light tokes and burgers, the film deftly subverts bro humor and takes much of the power back.
Penn played Kumar, obviously…and his heralded co-star, John Cho, became a lifelong friend. Cho and Penn then tried to purchase the fim rights to a Jhumpa Lahiri book called to Namesake.
Penn’s idol, Mira Nair already had them.
Penn contacted Nair for the second major time in his life, explaining the formative memories she had created on his path to modest success. She had already chosen her Gogol in The Namesake, but her thirteen-year-old son, Zohran Mamdani, simultaneously “pestered” her to cast his Kumar.
Nair listened to her son. She invited Penn to her office, where he was overjoyed to be offered chai by her female, brown assistant. It was such a departure from the hostile machismo that he scarred him along the way in white Hollywood.
Nair loved his audition, and replaced the other actor. She also let Mamdani meet Penn for the first time.
Penn thanked the tween.
“Doing Harold & Kumar meant that I got to audition for Mira Nair,” he wrote. “You can’t put a price tag on that.”
When he got the lead in the film, he openly wept. The shoot continued in a similar way. Penn’s autobiography details how impressed he was by the no-frills set and Nair’s lack of pretension.
“The Namesake remains the project of which I am most proud,” he extolled.
Bold words from a man who subsequently joined the Obama Administration.
In 2007, Penn was cast in House, a popular television series about an irreverent, detective-like doctor. It was the stable job Penn had longed for after the three Harold & Kumar films and countless box office flops. But after his House co-star, Olivia Wilde, convinced him to attend an event for Chicago Senator Barack Obama, Penn was seduced by his capacity for change. He knew he would not regret the chance to serve his country.
The humble, gumption attitude of the underestimated actor greatly aided him while canvassing the country. His book detailed tips about vending machines, mini fridges, and the Iowa caucus, about playing down his stoner character and judging fashionistas for shoe charities in times of crisis while admiring successful fundraising tactics. He recalled his phone soliciting days from Edison and his lessons as a demeaned assistant as tools for greatness.
Echoing his sentiments from the first Nair viewing, Penn was enthralled by Obama.
“It actually felt like we fit in,” he explained about celebrating Obama’s win. “We belonged here. In light of some of my darker experiences in middle school and Hollywood, this was not a feeling I was always used to.”
Along the way, Penn made some very powerful friends and pursued potent, impactful policy shifts. He discussed his desire to join the administration with Barack and Michelle Obama, and became the reason Sikhs could receive military haircut exemptions, Diwali became a big deal at the White House, and more simply, guys who looked like him could make it in politics.
Penn’s book was published in 2021, long before Mamdani captivated New York City and the world with his disarming, evocative, and intensely relatable campaign. According to the acknowledgements, Penn took five years to write his tell-all. But he thanks Mamdani again in those final pages, just 30 years old when it went to print.
Their relationship is hardly hidden. This week, for Diwali, Penn, Nair, and Mamdani went to Jackson Heights, Queens, and posed like the power team they are. Footage from an early rally shows Penn looking grave and wise in the shadows, perhaps orchestrating some of the potent, humorous but deadly serious language that evokes the hope and change once so alluring in Obama’s era. But Kaplen Uncle’s film legacy is mostly forgotten with the younger, more handsome face in front of the camera…even as it propels it.
Arguably, the most essential fuel in Kal Penn’s arsenal is the hate and bullying that nearly brought him down. Because, as a true American, Penn does not merely ignore it. He channels it. Simplifying Mamdani’s narrative down to his identity as a Muslim reveals the insecurities and fears of a zeitgeist, just as Harold & Kumar did for the frat bros, or Obama did for the far right. Now, with fears mounting around the war in Gaza, Mamdani’s New York has its finger on a global pulse. Is Penn to thank for that?
Perhaps.
“The Americans we were able to help in the Gulf lived mostly in Louisiana, Alabama…places where Obama is despised. These red states didn’t vote to elect him, and they wouldn’t be voting to reelect him. That didn’t matter to the president. Our job was to be there for them, no matter what their political affiliation.”
And thanks to Hollywood and strict Gujrati parents, Penn didn’t expect “a pat on the back” to keep doing his job.
Just as he doesn’t now.