No stranger to comedy or drama, Kal Penn is one of the most diversely talented actors to work in Hollywood over the past two decades. After breaking out opposite Ryan Reynolds as Taj Mahal in Van Wilder, Penn went on to star in the trio of beloved stoner comedies in the Harold & Kumar franchise.
Since then, Penn has transitioned to television, where he's starred in such dramatic fare as Designated Survivor and most recently, Clarice. As for his cinematic career of late, Penn hasn't starred in a feature film since 2018's The Ashram, an Indian drama from director Ben Rekhi.
The Sisterhood Of Night (2014) - 6.2/10
Based on a 1994 short story by Steven Millhauser, The Sisterhood of the Night refers to a coven of witches who overrun a suburban high school in New York. Penn plays Gordy Gambhir, a guidance counselor who becomes unwittingly involved in a witchy ritual.
Much of the drama revolves around Mary Warren (Georgie Henley), a teenager who takes a vow of silence and recruits two friends to form the Sisterhood, a cult-like sect that performs strange ceremonies in the woods. At its core, the movie highlights the dangers of online bullying.
A Very Harold & Kumar Christmas (2011) - 6.3/10
With diminishing returns, the third Harold & Kumar is the lowest-rated of the bunch. The holiday stoner comedy finds the lovable Harold (John Cho) and Kumar (Penn) on a quest to find the perfect Christmas Tree.
After accidentally torching his proud father-in-law's (Danny Trejo) Christmas tree, the two bumbling potheads traverse overcrowded New York to find an ideal replacement. Their epic sojourn includes encounters with several colorful characters while evading the Russian mob.
Van Wilder: Party Liaison (2002) - 6.4/10
Penn's first big breakout role came in National Lampoon's Van Wilder: Party Liaison, in which he played the memorable role of Indian exchange student Taj Mahal Badalandabad.
All Taj wants to do at college is act on his sexual inexperience, prompting resident playboy and all-around party animal Van Wilder (Ryan Reynolds) to take Taj under his wing and teach him the ropes of collegiate courtship. Penn reprised the role four years later in the sequel Van Wilder 2: The Rise of Taj.
American Desi (2001) - 6.6/10
In the first of several Indian or Indian-American movies he participated in, Penn starred in the 2001 rom-com American Desi. Written and directed by Piyush Dinker Pandya, the film follows Krishna (Deep Katdare), a college freshman forced to examine his heritage when assigned Indian roommates.
Prior to college, Krishna never really thought about his Indian background. But when he's arranged to live with Indian roommates and falls for an Indian girl named Nina (Purva Bedi), Krishna begins to question his identity. Penn plays Ajay, Krishna's roommate.
A Lot Like Love (2005) - 6.6/10
A Lot Like Love stars Ashton Kutcher and Amanda Peet as a pair of young suitors who meet and make love on a cross-country flight. When they decide they aren't right for each other, the friends with benefits continue their one-night stands with each other over the next seven years.
The elliptical story traces Oliver (Kutcher) and Emily's (Peet) NSA relationship one year at a time as they become closer and closer. Penn plays Jeeter, Oliver's friend and business partner who starts an online diaper venture.
Harold & Kumar Escape From Guantanamo Bay (2008) - 6.6/10
Four years after their epic journey to White Castle, Harold & Kumar found themselves profiled as terrorists and tossed into the Cuban prison camp at Guantanamo Bay.
In their daring escape mission, the two hilarious hash-heads run into a series of sordid characters while being chased by Ron Fox (Rob Corddry) and his heavily-armed team of federal agents. Traveling from Cuba to Florida to Texas, the duo seeks help from Harold's ex-girlfriend's rich fiancé.
Harold & Kumar Go To White Castle (2004) - 7.1/10
In addition to the natural chemistry exhibited between the two stars, the most refreshing aspect of the stoner comedy Harold & Kumar Go to White Castle is the way it shattered Indian-American and Korean-American stereotypes.
Despite their parental pressures, Harold (Cho) and Kumar (Penn) are typical American slackers and stoners who just want to get high and eat at their favorite fast food joint. Their mission to do just that turns into an episodic sitcom as the two meet several memorable characters and run into countless roadblocks along the way.
Bhopal: A Prayer For Rain (2014) - 7.2/10
Ravi Kumar's Bhopal: A Prayer for Rain is a multi-narrative film that chronicles the lives of several interrelated characters during the 1984 chemical spill in India that killed nearly 15,000 people and injured 100,000 more.
The film traces the lives of several Indian and American citizens before, during, and after the life-altering true event. Penn plays local journalist Motwani in the film, based on the real-life Rajkumar Keswani, the senior reporter who covered the Bhopal disaster when it happened.
Freshmen (1999) - 7.5/10
Aptly titled, the first feature film Penn appeared in ranks as his second-highest, per IMDb. Written and directed by Tom Huang, Freshmen is a coming-of-age college story about several first-year students struggling to find footing in the world.
The drama concerns four students from different cultural backgrounds: Chinese-American San (Huang), Black Tonisha (ND Brown), conservative and white Rick (Kurt Koehler), and liberal party-girl Judy (Margaret Scarborough), all of whom grapple with finding their identity.
The Namesake (2006) - 7.5/10
The best movie Penn has appeared in thus far is one he starred in as the top-billed leading actor. Directed by Mira Nair, The Namesake follows Nikhil, aka Gogol (Penn), an American-born Indian who tries his best to balance his family's traditions with his desire to be a typical New Yorker.
The drama crystallizes the cultural differences between Indians and Americans but also underscores the vast similarities as well. When Gogol meets and falls in love with Maxine (Jacinda Barrett), his loyalties are tested while his future faces more uncertainty than ever.