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1. Over the Edge (1979)
directed by Jonathan Kaplan
featuring Matt Dillon, Michael Kramer, Pamela Ludwig, Vincent Spano, Tom Fergus
The protagonists of Over the Edge are the teen-aged offspring of the residents of a planned suburban community. This bland little town has been ... More
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2. There's Something About Mary (1998)
directed by Bobby Farrelly, Peter Farrelly
featuring Ben Stiller, Cameron Diaz, Matt Dillon, Lee Evans, Chris Elliott
The Farrelly Brothers set this romantic comedy in their home state of Rhode Island. In 1985, when teen-nerd Ted Stroehmann (Ben Stiller) challenges a ... More
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3. Drugstore Cowboy (1989)
directed by Gus Van Sant
featuring Matt Dillon, Kelly Lynch, James LeGros, Heather Graham, James Remar
The operative word in Drugstore Cowboy is "drug". Matt Dillon plays the leader of a group of dopeheads who wander around the country robbing ... More
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4. One Night at McCool's (2001)
directed by Harald Zwart
featuring Liv Tyler, Matt Dillon, John Goodman, Paul Reiser, Michael Douglas
The debut project from co-star Michael Douglas' production company Further Films, this comic crime caper uses the narrative devices of multiple ... More
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5. You, Me and Dupree (2006)
directed by Anthony Russo, Joe Russo
featuring Owen Wilson, Kate Hudson, Matt Dillon, Seth Rogen, Amanda Detmer
A man is being driven crazy by his shiftless best friend, just as the layabout starts making nice with his wife and neighbors in this comedy. Carl ... More
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6. The Outsiders (1983)
directed by Francis Ford Coppola
featuring C. Thomas Howell, Matt Dillon, Ralph Macchio, Patrick Swayze, Rob Lowe
Teen rivalry in a small Southern town sets the stage for this dramatic interpretation of the novel by S.E. Hinton. Directed by Francis Ford Coppola, ... More
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7. Nothing But the Truth (2008)
directed by Rod Lurie
featuring Kate Beckinsale, Matt Dillon, Angela Bassett, Alan Alda, Vera Farmiga
A tense political drama ripped straight from the headlines, Rod Lurie's Nothing But the Truth tells the tale of a Washington, D.C. reporter who is ... More
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8. In & Out (1997)
directed by Frank Oz
featuring Kevin Kline, Joan Cusack, Matt Dillon, Debbie Reynolds, Wilford Brimley
Life is sweet for high-school English teacher and sports coach Howard Brackett (Kevin Kline); he's still living where he grew up, he has a good ... More
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9. Factotum (2006)
directed by Bent Hamer
featuring Matt Dillon, Lili Taylor, Marisa Tomei, Fisher Stevens, Didier Flamand
Norwegian director Bent Hamer follows up his quirky and critically acclaimed Kitchen Stories with a heartbreakingly humorous look at the life of ... More
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10. Employee of the Month (2003)
directed by Mitch Rouse
featuring Matt Dillon, Steve Zahn, Christina Applegate, Peter Jason, Andrea Bendewald
The directorial debut of actor/writer Mitch Rouse (Comedy Central's Strangers With Candy), Employee of the Month stars Matt Dillon as David Wells, a ... More
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11. Loverboy (2006)
directed by Kevin Bacon
featuring Kyra Sedgwick, Kevin Bacon, Blair Brown, Matt Dillon, Oliver Platt
A mother once neglected as child but possessed of a heart overflowing with love grows increasingly despondent as her beloved child begins to claim ... More
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12. Women and Men: In Love There are No Rules (1991)
directed by Kristi Zea, Mike Figgis, Walter Bernstein
featuring Andie MacDowell, Matt Dillon, Ray Liotta, Scott Glenn
Women and Men 2 is the second installment of HBO's short-story anthology series. In the first episode, Carson McCuller's "A Domestic Dilemma," Ray ... More
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13. Kansas (1988)
directed by David Stevens
featuring Matt Dillon, Andrew McCarthy, Leslie Hope, Brent Jennings
A drifter becomes both a bank robber and a hero in this crime thriller. Andrew McCarthy stars as Wade Corey, who hitches a ride on a freight train ... More
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14. The Saint of Fort Washington (1993)
directed by Tim Hunter
featuring Danny Glover, Matt Dillon, Rick Aviles, Nina Siemaszko, Ving Rhames
Danny Glover plays Jerry, a caring street person who takes a mentally retarded Matthew Dillon under his wing, teaching him the survival smarts so ... More
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15. Golden Gate (1994)
directed by John Madden
featuring Matt Dillon, Joan Chen, Bruno Kirby, Teri Polo, Tzi Ma
Playwright David Henry Hwang (M. Butterfly) wrote this ambitious epic that attempts to examine the communist witch hunts of the 1950s, racial ... More
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16. Rebel (1986)
directed by Michael Jenkins
featuring Matt Dillon, Debbie Byrne, Bryan Brown, Bill Hunter, Ray Barrett
This WW II musical is set in Australia and chronicles the exploits of a nightclub singer and the young Marine who loves her. She works in a Quonset ... More
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17. Crash (2005)
directed by Paul Haggis
featuring Sandra Bullock, Don Cheadle, Matt Dillon, Jennifer Esposito, Shaun Toub, Brendan Fraser
Issues of race and gender cause a group of strangers in Los Angeles to physically and emotionally collide in this drama from director and ... More
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18. Takers (2010)
directed by John Luessenhop
featuring Matt Dillon, Idris Elba, Tip "T.I." Harris, Chris Brown, Paul Walker, Hayden Christensen
A Los Angeles detective races to bust a group of notorious thieves before they can carry out a 20-million-dollar heist in this crime thriller from ... More
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19. My Bodyguard (1980)
directed by Tony Bill
featuring Chris Makepeace, Adam Baldwin, Matt Dillon, Ruth Gordon, John Houseman, Martin Mull
This quietly compelling film explores the hardships and anxieties of high school with intelligence, sensitivity, warmth and humor. Chris Makepeace ... More
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20. Target (1985)
directed by Arthur Penn
featuring Gene Hackman, Matt Dillon, Gayle Hunnicutt, Victoria Fyodorova, Josef Sommer
Arthur Penn takes a crack at subverting the espionage film genre in Target. Walter Lloyd (Gene Hackman) is a quiet and unassuming lumberyard owner in ... More
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21. Herbie: Fully Loaded (2005)
directed by Angela Robinson
featuring Lindsay Lohan, Justin Long, Breckin Meyer, Matt Dillon, Michael Keaton, Cheryl Hines
The world's wackiest Volkswagen is back in action in this action comedy. Maggie Peyton (Lindsay Lohan) is the 18-year-old daughter of Ray Peyton Sr. ... More
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22. Rumble Fish (1983)
directed by Francis Ford Coppola
featuring Herb Rice, Matt Dillon, Mickey Rourke, Diane Lane, Dennis Hopper, Diana Scarwid
One of two S.E. Hinton novels Francis Ford Coppola directed in 1983, Rumble Fish is a stylized black-and-white film about the death of gang culture ... More
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23. To Die For (1995)
directed by Gus Van Sant
featuring Nicole Kidman, Matt Dillon, Joaquin Phoenix, Casey Affleck, Illeana Douglas, Alison Folland
The price of fame is murder -- or at least it is in the mind of one woman in New Hampshire. Suzanne Stone (Nicole Kidman) has spent most of her life ... More
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24. Beautiful Girls (1996)
directed by Ted Demme
featuring Timothy Hutton, Matt Dillon, Noah Emmerich, Annabeth Gish, Michael Rapaport, Lauren Holly, Mira Sorvino, Uma Thurman
A high-school reunion in a snowy New England town brings together a diverse band of former classmates. They include NYC pianist Willie Timothy Hutton ... More
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25. The Flamingo Kid (1984)
directed by Garry Marshall
featuring Matt Dillon, Richard Crenna, Hector Elizondo, Jessica Walter, Fisher Stevens, Janet Jones
Set in 1963, The Flamingo Kid finds 18-year-old Brooklynite Matt Dillon, the son of blue-collar Hector Elizondo, getting a taste of the Good Life by ... More
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