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The Best Kal Penn Movies

Updated September 23, 2019 812 votes 103 voters 16.1k views29 items

List RulesVote for your favorite movies, regardless of critic reviews or how big the role was.

List of the best Kal Penn movies, ranked best to worst with movie trailers when available. Kal Penn's highest grossing movies have received a lot of accolades over the years, earning millions upon millions around the world. The order of these top Kal Penn movies is decided by how many votes they receive, so only highly rated Kal Penn movies will be at the top of the list. Kal Penn has been in a lot of films, so people often debate each other over what the greatest Kal Penn movie of all time is. If you and a friend are arguing about this then use this list of the most entertaining Kal Penn films to end the squabble once and for all.

If you think the best Kal Penn role isn't at the top, then upvote it so it has the chance to become number one. The greatest Kal Penn performances didn't necessarily come from the best movies, but in most cases they go hand in hand.

Epic Movie and Freshmen are a great starting point for your to rank your favorites on this list

"This list answers the questions, "What are the best Kal Penn movies?" and "What are the greatest Kal Penn roles of all time?"

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  • 1
    Harold & Kumar Escape from Guantanamo Bay
    89
    13

    Harold & Kumar Escape from Guantanamo Bay

    Neil Patrick Harris, Danneel Ackles

    Released2008

    Directed byHayden Schlossberg, Jon Hurwitz

    Harold & Kumar Escape from Guantanamo Bay is a 2008 American stoner action comedy film, the... more on Wikipedia
  • 2
    Harold & Kumar Go to White Castle
    82
    10

    Released2004

    Directed byDanny Leiner

    Harold & Kumar Go to White Castle is a 2004 American stoner comedy film directed by Danny... more on Wikipedia

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    #87 of 554 The Greatest Guilty Pleasure Movies#16 of 204 The Best Drug Movies of All Time

  • 3
    A Very Harold & Kumar 3D Christmas
    58
    11

    A Very Harold & Kumar 3D Christmas

    Neil Patrick Harris, Danneel Ackles

    Released2011

    Directed byTodd Strauss-Schulson

    A Very Harold & Kumar 3D Christmas is a 2011 3D stoner comedy Christmas film directed by Todd... more on Wikipedia

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    #79 of 102 The Best Third Films In A Movie Series#34 of 46 The Best John Cho Movies

  • 4
    National Lampoon's Van Wilder
    46
    6

    National Lampoon's Van Wilder

    Ryan Reynolds, Tara Reid

    Released2002

    Directed byWalt Becker

    National Lampoon's Van Wilder is a 2002 comedy film directed by Walt Becker that stars Ryan... more on Wikipedia

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    #611 of 1,647 The Most Rewatchable Movies#267 of 1,137 The Absolute Funniest Movies Of All Time

  • 5
    Van Wilder: The Rise of Taj
    36
    8

    Van Wilder: The Rise of Taj

    Lauren Cohan, Kal Penn

    Released2002

    Directed byMort Nathan

    National Lampoon's Van Wilder: The Rise of Taj is a 2006 sequel to the 2002 comedy National... more on WikipediaAmazon_watch buy button

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    #19 of 23 The Funniest Movies About College#31 of 34 The Best Movies About Dating In College

  • 6
    Epic Movie
    36
    15

    Epic Movie

    Carmen Electra, Jennifer Coolidge

    Released2007

    Directed byAaron Seltzer, Jason Friedberg

    Epic Movie is a 2007 American parody film directed and written by Jason Friedberg and Aaron... more on Wikipedia

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    #693 of 922 The All-Time Greatest Comedy Films#3 of 94 The Worst January Movie Releases

  • 7
    Harold & Kumar Go to Amsterdam
    21
    4

    Harold & Kumar Go to Amsterdam

    Danneel Ackles, Kal Penn

    Released2008

    Directed byHayden Schlossberg, Jon Hurwitz

    Harold & Kumar Go to Amsterdam is a 2008 short comedy film directed and written by Jon Hurwitz...Amazon_watch buy button
  • 8
    Superman Returns
    28
    13

    Superman Returns

    Marlon Brando, Kevin Spacey

    Released2006

    Directed byBryan Singer

    Superman Returns is a 2006 American superhero film directed and produced by Bryan Singer. It... more on Wikipedia

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    #53 of 97 The Worst Superhero Movies Ever Made#138 of 167 The Best Superhero Movies Ever Made

  • 9
    Son of the Mask
    26
    15

    Son of the Mask

    Alan Cumming, Bob Hoskins

    Released2005

    Directed byLawrence Guterman

    Son of the Mask is a 2005 American fantasy family-comedy film directed by Lawrence Guterman... more on Wikipedia

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    #1 of 225 The Worst Sequels Of All Time#23 of 70 The Dumbest Movie Sequel Titles

  • 10
    Dude, Where's the Party?
    13
    2

    Dude, Where's the Party?

    Kal Penn, Serena Varghese

    Released2003

    Directed byBenny Mathews

    Dude, Where's the Party? aka Where's the party yaar? is a 2003 film directed by Benny Mathews.... more on Wikipedia
  • 11
    Love Don't Cost a Thing
    18
    10

    Love Don't Cost a Thing

    Nicole Scherzinger, Christina Milian

    Released2003

    Directed byTroy Bailey

    Love Don't Cost a Thing, stylized as Love Don't Co$t a Thing, is a 2003 teen comedy film... more on Wikipedia

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  • 12
    Deck the Halls
    16
    10

    Deck the Halls

    Danny DeVito, Kristin Chenoweth

    Released2006

    Directed byJohn Whitesell

    Deck the Halls is a 2006 American family comedy film set during the Christmas season in... more on Wikipedia

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    #62 of 134 The Best Christmas Movies of All Time#68 of 81 The Best Winter Movies

  • 13
    The Namesake
    14
    8

    The Namesake

    Kal Penn, Irrfan Khan

    Released2006

    Directed byMira Nair

    The Namesake is a 2006 film which was released in the United States on March 9, 2007,... more on Wikipedia

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    #15 of 27 Movies Based On Books You Should Have Read In 8th Grade#169 of 179 The Best Family Drama Movies of All Time

  • 14
    Ball & Chain
    14
    8

    Ball & Chain

    Kal Penn, nm2147526

    Released2006

    Directed byShiraz Jafri

    When Ameet and Saima's Indian-American families arrange for them to be married they will do... more on Wikipedia
  • 15
    4
    2

    Freshmen

    Kal Penn, Patrick Gorman

    Released1999

    Directed byTom Huang

    Amazon_watch buy button
  • 16
    Two Sisters
    2
    4

    Two Sisters

    Margaret Cho, Kal Penn

    Released2008

    Directed byMargaret Cho

    Two Sisters is a 2008 television film directed by Margaret Cho.Amazon_watch buy button
  • 17
    2
    6

    Express: Aisle to Glory

    Kal Penn

    Released1998

    Directed byJonathan Buss

    Express: Aisle to Glory is a 1998 comedy short film written and directed by Jonathan Buss. It... more on WikipediaAmazon_watch buy button
  • 18
    Dancing in Twilight
    0
    4

    Dancing in Twilight

    Mimi Rogers, Kal Penn

    Released2005

    Directed byBob Roe

    Dancing in Twilight is a 2005 film directed by Bob Roe.Amazon_watch buy button
  • 19
    American Desi
    13
    8

    American Desi

    Kal Penn, Deep Katdare

    Released2001

    Directed byPiyush Dinker Pandya

    American Desi is a 2001 American film with Indian influence, notable for featuring many... more on Wikipedia
  • 20
    Sueño
    0
    4

    Sueño

    Nadine Velazquez, John Leguizamo

    Released2005

    Directed byJane Chabria

    Sueño is a 2005 comedy-drama film directed by Renée Chabria that stars John Leguizamo, Ana... more on WikipediaAmazon_watch buy button
  • 21
    Bachelor Party Vegas
    10
    4

    Bachelor Party Vegas

    Kathy Griffin, Jaime Pressly

    Released2006

    Directed byEric Bernt

    Bachelor Party Vegas is a comedy film that was released in 2006 starring Kal Penn, Jonathan... more on Wikipedia
  • 22
    Hector
    0
    4

    Hector

    Kal Penn, Skyler Stone

    Released2002

    Directed bySteffen Schlachtenhaufen

    Amazon_watch buy button
  • 23
    Malibu's Most Wanted
    14
    10

    Malibu's Most Wanted

    Snoop Dogg, Bo Derek

    Released2003

    Directed byJohn Whitesell

    Malibu's Most Wanted is a 2003 comedy film written by and starring Jamie Kennedy and... more on Wikipedia

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    #113 of 142 The Most Rewatchable Comedy Movies#120 of 124 The Most Rewatchable Movie Musicals

  • 24
    Cosmopolitan
    0
    4

    Cosmopolitan

    Carol Kane, Kal Penn

    Released2003

    Directed byNisha Ganatra

    Cosmopolitan is a 2003 American independent film starring Roshan Seth and Carol Kane, and... more on Wikipedia
  • 25
    Homeland Security
    10
    6

    Homeland Security

    Kal Penn, Marisol Nichols

    Released2004

    Directed byDaniel Sackheim

    Homeland Security is a 2004 made-for-TV film, which was intended as a pilot for a series which... more on Wikipedia