The Best Chris Klein Movies

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Updated March 15, 2024 23 items
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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.

  • Here on Earth
    1
    Chris Klein, Leelee Sobieski, Josh Hartnett
    23 votes
    Kelley Morse (Chris Klein), who is cocky and brash, normally would never have crossed paths with the residents of a small town near his posh private school. But when he races his new car against a local boy and destroys a diner, he is sentenced to rebuild the diner and falls in love with the owner's daughter (Leelee Sobieski).
  • American Reunion
    2
    Jason Biggs, Alyson Hannigan, Chris Klein
    11 votes
    In the summer of 1999, four small-town Michigan boys began a quest to lose their virginity. In the ensuing years, Jim (Jason Biggs) has married Michelle (Alyson Hannigan), though Kevin (Thomas Ian Nicholas) has left Vicky (Tara Reid). Oz (Chris Klein) has grown apart from Heather (Mena Suvari), but Finch still has the hots for Stiffler's (Seann William Scott) mom (Jennifer Coolidge). These lifelong friends have come home to reminisce about -- and become inspired by -- their former teen selves.
  • We Were Soldiers
    3
    Mel Gibson, Madeleine Stowe, Greg Kinnear
    17 votes
    An unflinching portrayal of the Vietnam War, We Were Soldiers dives into the Battle of La Drang. Lieutenant Colonel Hal Moore (Mel Gibson) leads his men in a brutal fight against North Vietnamese soldiers. The movie also features Sergeant Major Basil Plumley (Sam Elliott), an indomitable figure whose bravery shines amidst the chaos. Director Randall Wallace's vision crafts a vivid picture of war's grim reality, eschewing romanticized heroism for stark truth. A notable entry in the war genre, We Were Soldiers captures the harsh realities faced by those on the battlefront.
  • Just Friends
    4
    Ryan Reynolds, Amy Smart, Anna Faris
    13 votes
    High school student Chris Brander (Ryan Reynolds) loves his best friend, Jamie Palamino (Amy Smart). He finally confesses his feelings, but she tells him that she just wants to be friends, and he leaves town in shame. Ten years later, Chris is a successful record executive and involved with self-absorbed pop star Samantha James (Anna Faris). He still pines for Jamie, though, and when his plans to go to Paris for the holidays fall through, he returns to his hometown to try and win her heart.
  • American Pie
    5
    Jason Biggs, Shannon Elizabeth, Alyson Hannigan
    19 votes
    In American Pie, a raucous teen comedy, five high school friends - Jim (Jason Biggs), Oz (Chris Klein), Kevin (Thomas Ian Nicholas), Finch (Eddie Kaye Thomas), and Stifler (Seann William Scott) - make a pact to lose their virginity by prom night. The film, peppered with iconic scenes and unforgettable one-liners, explores the trials and tribulations of adolescence in a humorous yet honest way. As graduation looms, the boys navigate relationships, peer pressure, and their own insecurities. Their misadventures lead to hilarious situations that have since become staples of the genre. Though not an award winner, its impact on pop culture is undeniable.
  • Say It Isn't So
    6
    Chris Klein, Heather Graham, Orlando Jones
    12 votes
    Boy (Chris Klein) meets girl (Heather Graham) ; boy falls in love (and had wild, non-stop sex) with girl; boy loses girl... when they discover they are brother and sister! But when he learns that he's the victim of the ultimate case of mistaken identity, the lovesick young man -- whom everyone still thinks is after some taboo thrills -- must race across the country to stop her from marrying another man.
  • Election
    7
    Matthew Broderick, Reese Witherspoon, Chris Klein
    14 votes
    Vying for victory, the movie Election unfurls a darkly comedic tale of high school politics. Tracy Flick (Reese Witherspoon), an ambitious and overachieving student, is determined to win the student council elections at all costs. Jim McAllister (Matthew Broderick), a popular teacher, perceives her relentless ambition as dangerous and plots to derail her campaign. This satirical drama, directed by Alexander Payne, captures the quirks of suburban life and teenage ambition with sharp wit. A critical darling, Election earned an Academy Award nomination for Best Adapted Screenplay. It's a riveting exploration of ethics, ambition, and the lengths some will go to win.
  • American Pie 2
    8
    Jason Biggs, Shannon Elizabeth, Alyson Hannigan
    16 votes
    The sequel to the hit comedy follows the exploits of Jim Levenstein (Jason Biggs), Kevin Myers (Thomas Ian Nicholas), and their high school friends as they navigate the challenges and delights of college life. After a year apart, they reunite for a summer of fun, pranks, and romance at a beach house. American Pie 2, filled with raunchy humor and awkward moments, paints an unfiltered picture of young adulthood. Despite the hilarity, it also touches upon themes of friendship and growing up in its own unique way.
  • The Valley of Light
    9
    Gretchen Mol, Jackson Rathbone, Chris Klein
    11 votes
  • Play Dead
    10

    Play Dead

    Sasha Alexander, Fred Durst, Chris Klein
    6 votes
    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 former TV action star in need of a comeback. After a failed audition, he ends up snowbound in a remote town in Nevada overrun with meth dealers including Merle and their dimwitted henchman. After Reno finds the body of a dead DEA agent, he reunites with his former co-stars including Devon in order to save the town and himself.
  • The United States of Leland
    11
    Don Cheadle, Ryan Gosling, Chris Klein
    10 votes
    A withdrawn young man, Leland Fitzgerald (Ryan Gosling) is imprisoned for the murder of a mentally disabled boy, who also happened to be the brother of his girlfriend, Becky (Jena Malone). As the community struggles to deal with the killing, Pearl Madison (Don Cheadle), a teacher at the prison, decides to write about Leland's case. Meanwhile, others affected by the murder, including Becky and her sister, Julie (Michelle Williams), must contend with their own problems.
  • Street Fighter: The Legend of Chun-Li
    12
    Kristin Kreuk, Chris Klein, Neal McDonough
    9 votes
    In Bangkok, Bison (Neal McDonough), a crime boss, and his henchmen (Michael Clarke Duncan, Josie Ho, Taboo) begin a bid for power in the city's slum, crushing everyone who gets in their way. As the violence escalates, a team of heroes emerges to bring Bison to justice. Fighting on the side of good are Chun-Li (Kristin Kreuk), martial-arts master Gen (Robin Shou), Interpol agent Charlie Nash (Chris Klein) and his partner, Maya Sunee (Moon Bloodgood).
  • Rollerball
    13
    Chris Klein, Jean Reno, LL Cool J
    11 votes
    Jonathan (Chris Klein) is the most popular player in the fastest and most extreme sport of all time: rollerball. Along with teammates Marcus (LL Cool J) and Aurora (Rebecca Romijn-Stamos), Jonathan is giving viewers what they want: visceral thrills, breakneck speed, and head-slamming action. Things go wrong when rollerball's creator, Petrovich (Jean Reno), realizes that serious on-court accidents bring higher ratings. Soon Jonathan and his friends are playing for their lives.
  • The Good Life
    14
    Zooey Deschanel, Bill Paxton, Chris Klein
    6 votes
    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.
  • American Dreamz
    15
    Hugh Grant, Dennis Quaid, Mandy Moore
    7 votes
    Hoping to shock the president (Dennis Quaid) out of an apparent nervous breakdown, the White House chief of staff (Willem Dafoe) books him as a guest judge on the country's hottest TV talent show. With a ruthless host (Hugh Grant), a conniving singer (Mandy Moore), and a sleeper-cell terrorist in the mix, the stage is set for an unforgettable program.
  • Hank and Mike
    16
    Joe Mantegna, Chris Klein, Boyd Banks
    7 votes
    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 fired and try their hand at an assortment of odd jobs. The film premiered in 2008 at the NATPE NextGen Film Festival and was slated for general audience release on October 24, 2008 in the United States. The film was released in Canada on March 27, 2009.
  • New York City Serenade
    17

    New York City Serenade

    Jamie Lynn Sigler, Freddie Prinze, Jr.
    7 votes
    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 International Film Festival. The film takes it title from the Bruce Springsteen song of the same name from 1973.
  • The Long Weekend
    18
    Cobie Smulders, Evangeline Lilly, Erica Cerra
    9 votes
    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 Smulders.
  • Day Zero
    19
    Ginnifer Goodwin, Elijah Wood, Elisabeth Moss
    5 votes
    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 young men, who have just received their induction notices and have 30 days to report for duty, must battle their political views before making a decision that will change their lives forever. This is American director Cole's debut film. It premiered at the 2007 Tribeca Film Festival and opened in limited release in the United States on January 18, 2008. The film stars Elijah Wood, Chris Klein and Jon Bernthal. It also features Ginnifer Goodwin, Sofia Vassilieva, Elisabeth Moss and Ally Sheedy.
  • The Six Wives of Henry Lefay
    20
    Tim Allen, Elisha Cuthbert, Paz Vega
    5 votes
    A presumed-dead man's current wife and former wives squabble over his funeral arrangements.
  • Lenexa, 1 Mile
    21

    Lenexa, 1 Mile

    Paul Wesley, Chris Klein, William Baldwin
    6 votes
    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 Co-Star.
  • Sam
    22

    Sam

    Anna Chlumsky, Chris Klein, James Lafferty
    4 votes
    Sam is a 2011 comedy film written by John A. Gallagher and Nicholas Brooks and directed by John A. Gallagher.
  • Caught in the Crossfire
    23
    50 Cent, Chris Klein, Christine Lakin
    4 votes
    Caught in the Crossfire is 2010 American crime drama film directed by Brian A Miller. It stars Adam RodrĂ­guez, 50 Cent, and Richard T. Jones. The film was released direct-to-DVD on July 20, 2010.