The Best Chris Klein Movies 

Updated June 11, 2019 275 votes 63 voters 7.7k views 23 items

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

List of the best Chris Klein movies, ranked best to worst with movie trailers when available. Chris Klein'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 Chris Klein movies is decided by how many votes they receive, so only highly rated Chris Klein movies will be at the top of the list. Chris Klein has been in a lot of films, so people often debate each other over what the greatest Chris Klein movie of all time is. If you and a friend are arguing about this then use this list of the most entertaining Chris Klein films to end the squabble once and for all.

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

List ranges from The Six Wives of Henry Lefay to The Valley of Light, plus much more.

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

If Chris Klein movies are your thing, then check out the greatest movies by Freddie Prinze, Jr. and Adrian Grenier too.

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Josh Hartnett, Leelee Sobieski, Annette O'Toole

Released: 2000

Directed by: Mark Piznarski

Here on Earth is a 2000 romantic drama film directed by Mark Piznarski with a screenplay by Michael Seitzman. It stars Chris Klein, Leelee Sobieski, and Josh Hartnett. The original music score ...more

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#190 of 199 The Biggest Tearjerker Movies of All Time #242 of 266 The Best Teen Romance Movies #16 of 27 The Best Josh Hartnett Movies

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Mel Gibson, Lyndon B. Johnson, Jon Hamm

Released: 2002

Directed by: Randall Wallace

We Were Soldiers is a 2002 film that dramatizes the Battle of Ia Drang on November 14, 1965. The film was directed by Randall Wallace and stars Mel Gibson. It is based on the book We Were ...more

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Ryan Reynolds, Anna Faris, Amy Smart

Released: 2005

Directed by: Roger Kumble

Just Friends is a 2005 American romantic comedy and Christmas film directed by Roger Kumble, and starring Ryan Reynolds, Amy Smart, Anna Faris, Chris Klein and Christopher Maquette. The plot ...more

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#193 of 802 The Greatest Chick Flicks Ever Made #819 of 1,210 The Absolute Funniest Movies Of All Time #578 of 1,026 The All-Time Greatest Comedy Films

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Alyson Hannigan, Tara Reid, Shannon Elizabeth

Released: 1999

Directed by: Chris Weitz, Paul Weitz

American Pie is a 1999 teen comedy film written by Adam Herz and directed by brothers Paul and Chris Weitz, in their directorial film debut. It is the first film in the American Pie theatrical ...more

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'American Pie' Is A Nightmarish Vision Of Late '90s High School Life #16 of 493 The Funniest '90s Movies #284 of 1,699 The Most Rewatchable Movies

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Reese Witherspoon, Matthew Broderick, Chris Klein

Released: 1999

Directed by: Alexander Payne

Election is a 1999 American comedy film directed and written by Alexander Payne and adapted by him and Jim Taylor from Tom Perrotta's 1998 novel of the same title. The plot revolves around a ...more

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American Pie 2 is listed (or ranked) 6 on the list The Best Chris Klein Movies
Alyson Hannigan, Tara Reid, Shannon Elizabeth

Released: 2001

Directed by: James B. Rogers

American Pie 2 is a 2001 American comedy film and the sequel to the 1999 film American Pie and the second film in the American Pie film series. It was written by Adam Herz and directed by James ...more

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#480 of 1,699 The Most Rewatchable Movies #278 of 1,210 The Absolute Funniest Movies Of All Time #397 of 1,026 The All-Time Greatest Comedy Films

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Heather Graham, Sarah Silverman, Sally Field

Released: 2001

Directed by: James B. Rogers

Say It Isn't So is a 2001 American comedy film starring Chris Klein and Heather Graham as two young lovers who come to believe that they are actually siblings. The film is directed by J.B. ...more
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Alyson Hannigan, Neil Patrick Harris, Tara Reid

Released: 2012

Directed by: Hayden Schlossberg, Jon Hurwitz

American Reunion is a 2012 ensemble comedy film written and directed by Jon Hurwitz and Hayden Schlossberg. It is the fourth installment in the American Pie theatrical series and eighth ...more

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#1,151 of 1,699 The Most Rewatchable Movies #708 of 1,210 The Absolute Funniest Movies Of All Time #467 of 1,026 The All-Time Greatest Comedy Films

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Gretchen Mol, Jackson Rathbone, Chris Klein

Released: 2007

Directed by: Brent Shields

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Play Dead Sasha Alexander, Fred Durst, Chris Klein

Released: 2009

Directed by: Jason Wiles

Play Dead is a film released in 2009 written by Jason Wiles and Shem Bitterman, directed by Jason Wiles and starring Chris Klein, Fred Durst, and Jake Busey. The story is about Ronnie Reno, a ...more
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Kerry Washington, Ryan Gosling, Kevin Spacey

Released: 2003

Directed by: Matthew Ryan Hoge

The United States of Leland is a 2003 American drama film written and directed by Matthew Ryan Hoge that follows a meek teenage boy, the eponymous Leland, who has inexplicably committed a ...more

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Elisha Cuthbert, Andie MacDowell, Jenna Elfman

Released: 2009

Directed by: Howard Michael Gould

The Six Wives of Henry Lefay is a 2009 American comedy film starring Elisha Cuthbert and Tim Allen. A grieving daughter tries to arrange her father's funeral, while putting up with all of his ...more
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Carmen Electra, Mandy Moore, Willem Dafoe

Released: 2006

Directed by: Paul Weitz

American Dreamz is a 2006 comedy/parody film that satirizes both American politics and popular entertainment. Director/producer/writer Paul Weitz has stated that the movie is meant to satirize ...more

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Kristin Kreuk, Moon Bloodgood, Michael Clarke Duncan

Released: 2009

Directed by: Andrzej Bartkowiak

Street Fighter: The Legend of Chun-Li is a 2009 live-action film based on the Street Fighter series of video games. It follows the quest of Street Fighter character Chun-Li, who is portrayed by ...more

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P!nk, Rebecca Romijn, LL Cool J

Released: 2002

Directed by: John McTiernan

Rollerball is a 2002 remake of the 1975 science-fiction film of the same name. This updated version stars Chris Klein, Jean Reno, LL Cool J, Rebecca Romijn, and Naveen Andrews. It was directed ...more

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Cobie Smulders, Evangeline Lilly, Erica Cerra

Released: 2006

Directed by: Pat Holden

The Long Weekend is a 2005 Canadian film starring Chris Klein and Brendan Fehr as two brothers, Cooper and Ed Waxman. It also stars Chelan Simmons, Paul Campbell, Chandra West, and Cobie
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Zooey Deschanel, Bill Paxton, Chris Klein

Released: 2007

Directed by: Steve Berra

The Good Life is a 2007 film written and directed by Stephen Berra, starring Mark Webber, Zooey Deschanel, Patrick Fugit, Bill Paxton, Drea de Matteo, Harry Dean Stanton, and Chris Klein.
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50 Cent, Chris Klein, Christine Lakin

Released: 2010

Directed by: Brian A. Miller

Caught in the Crossfire is 2010 American crime drama film directed by Brian A Miller. It stars Adam Rodríguez, 50 Cent, and Richard T. Jones. The film was released direct-to-DVD on July
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Ginnifer Goodwin, Elijah Wood, Elisabeth Moss

Released: 2007

Directed by: Bryan Gunnar Cole

Day Zero is a 2007 American film directed by Bryan Gunnar Cole and written by Robert Malkani. Set in the near future when global terrorism has forced the military to reinstate the draft, three ...more
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Joe Mantegna, Chris Klein, Boyd Banks

Released: 2007

Directed by: Matthiew Klinck

Hank and Mike is a 2008 comedy film directed by Matthiew Klinck, from a screenplay written by Paolo Mancini and Thomas Michael. The film tells the story of two blue-collar Easter Bunnies who get ...more
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New York City Serenade Jamie Lynn Sigler, Freddie Prinze, Jr.

Released: 2008

Directed by: Frank Whaley

New York City Serenade is a 2007 comedy-drama film written and directed by Frank Whaley and starring Freddie Prinze, Jr., Chris Klein and Jamie-Lynn Sigler. It made its debut at the 2007 Toronto ...more
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Lenexa, 1 Mile Paul Wesley, Chris Klein, William Baldwin

Directed by: Jason Wiles

Lenexa, 1 Mile is drama film written by Jason Wiles, Shem Bitterman, and directed by Wiles. The film stars Josh Stewart, Jason Ritter, and William Baldwin. Austin Nichols and Paul Wesley
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Sam Anna Chlumsky, Chris Klein, James Lafferty

Released: 2011

Directed by: John A. Gallagher

Sam is a 2011 comedy film written by John A. Gallagher and Nicholas Brooks and directed by John A. Gallagher.