Born first generation Indian-American in New Jersey—his parents emigrated with little money—Penn yearned to perform since he was a kid. Though his parents hoped it was a passing phase and he would eventually become a doctor or lawyer, he continued to pursue his dream, attending the Freehold Regional High School for Performing Arts in Englishtown. His interest held when joined the theater program at the University of California, Los Angeles. With a resume full of high school productions and community theater, he began the arduous process of submitting head shots and going on auditions. The response to his efforts, however, was tepid. Recognizing the problem, his agent persuaded him to Anglicize his name—originally Kalpen Modi—which Penn thought wouldn’t make a difference. For the hell of it, he split his first name in two, added an ‘N’ to the second part and resubmitted his headshots. Auditions went up by 50 percent.
Opportunities began to trickle in. After appearing in episodes of “Sabrina, the Teenage Witch” (ABC-WB, 1996-2003) and “Spin City” (ABC, 1996-2002), he made his first movie, “American Desi” (2001), in which he played the hip-hop-obsessed roommate of a college student (Deep Katdare) from a traditional Indian family. Meantime, his profile on television increased: he played a young man wearing a Fez in an episode of “Angel” (WB, 1999-2004) and turned up on episodes of “ER” (NBC, 1994- ), “The Agency” (CBS, 2001-2003) and “NYPD Blue” (ABC, 1993- ). Penn then made the disparaging choice of playing the Indian exchange student, Taj Mahal, in “National Lampoon’s Van Wilder.” Originally uninterested in the part because of the character’s name and thick Indian accent, Penn was convinced by his agent to take the part. But despite the promises of rampant sex, ample gross-outs and the star power of Ryan Reynolds and Tara Reid, “Van Wilder” received a critical drubbing and soon whimpered out of theaters.
In 2003, Penn saw himself in three theatrically released movies. He appeared in the Indian-made comedy, “Where’s the Party Yaar?”, playing a brash first generation Indian-American whose cousin arrives from India to attend his college, putting a crimp in his hard-partying style. After playing an Arab who shows off a rocket-powered grenade launcher that he received as a Christmas gift in “Malibu’s Most Wanted,” he appeared in the mediocre and ultimately forgettable romantic comedy, “Love Don’t Cost a Thing.” On television, he played a medical student renting a room from the parents of a struggling actor (Anthony Anderson) who returns home to raise his eight year-old son in “All About the Andersons” (WB, 2003-2004). Originally replacing actor Paul Bartholomew after the pilot episode, Penn was later replaced by Aimee Garcia.
Penn’s big break was “Harold & Kumar Go to White Castle,” a teen comedy with plenty of sex and gross-out jokes, but also possessing three-dimensional main characters who long for more than just tiny burgers after a few bong tokes. Penn and his co-star John Cho (“Better Luck Tomorrow”) played Ivy League-educated roommates who, after indulging in some Cannabis sativa, suddenly crave White Castle hamburgers. The quest for the mythical sandwiches becomes a wild journey of self-discovery, as the two underdogs learn more in one night than they ever did in college. Though perfect for the part, Penn had to earn his spot despite meeting the screenwriters at a party. Producers scoured the country and beyond for the right Harold and Kumar in an extensive audition process. After several auditions over the course of three months, Penn got the part and was thrilled to finally play a character devoid of the stereotypical trappings that plagued earlier roles. The film ultimately garnered a widespread cult fan base.
The exposure from “Harold and Kumar” allowed Penn to play more diverse roles in larger projects. He appeared in an episode of “Six Feet Under” (HBO, 2001- ) and was cast in a few Hollywood blockbusters, including the decade-late sequel, “Son of the Mask” (2005), with Jamie Kennedy, and the lame romantic comedy “A Lot Like Love” (2005), both of which failed to spark a modicum of interest with critics and audiences. Meanwhile, Penn was cast to appear in the road comedy “Vegas Baby” (lensed 2005) and Lex Luthor's genius lackey Stanford in the long-awaited cinematic return of the Man of Steel, “Superman Returns” (2006). Meanwhile, Penn was set to star in the sequel “Van Wilder Deux: The Rise of Taj” (2006), reviving his character to take center stage, as Taj goes to Oxford University to study and show the uptight student body how to have a good time. For his next feature, “The Namesake” (2006), Penn went a different direction into drama, playing the son of Indian immigrants whose search for his own unique identity might cause him to lose touch with his heritage.