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1. Reservoir Dogs (1992)
directed by Quentin Tarantino
featuring Harvey Keitel, Tim Roth, Michael Madsen, Chris Penn, Steve Buscemi, Lawrence Tierney
In 1992, Reservoir Dogs transformed Quentin Tarantino practically overnight from an obscure, unproduced screenwriter and part-time actor to the most ... More
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2. Trail of a Serial Killer (1998)
directed by Damian Lee
featuring Michael Madsen, Chris Penn, Chad McQueen
For 10 years, FBI agent Jason Enola has been obsessed with capturing a particularly clever serial killer who surrounds his victims with a series of ... More
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3. Redemption (2002)
directed by Art Camacho
featuring Don "The Dragon" Wilson, Chris Penn, James Russo
When a fallen cop turns to a life of crime to support both himself and his young son, the choices he makes may lead to deadly consequences in this ... More
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4. Footloose (1984)
directed by Herbert Ross
featuring Kevin Bacon, Lori Singer, John Lithgow, Dianne Wiest, Chris Penn
In this lively adolescent-oriented musical, a city kid attempts to adapt to life in an ultra-conservative backwater Midwestern town. Once there, he ... More
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5. Corky Romano (2001)
directed by Rob Pritts
featuring Chris Kattan, Vinessa Shaw, Peter Falk, Peter Berg, Chris Penn
Saturday Night Live cast member Chris Kattan stars in this mob comedy as Corky Romano, a veterinarian with a penchant for pop music from the '80s. As ... More
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6. Best of the Best 2 (1993)
directed by Robert Radler
featuring Eric Roberts, Phillip Rhee, Chris Penn, Edan Gross, Ralph Moeller
In Best of the Best 2, Alex Grady and his partner, Tommy Lee, turn their karate talents toward crime fighting. An illegal fighting club, headed by ... More
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7. Holly (2007)
directed by Guy Moshe
featuring Ron Livingston, Thuy Nguyen, Virginie Ledoyen, Chris Penn, Udo Kier
A two-bit criminal gets a shot at redemption while traveling through Southeast Asia in this 2006 drama from director Guy Moshe. Ron Livingston stars ... More
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8. Murder By Numbers (2002)
directed by Barbet Schroeder
featuring Sandra Bullock, Ryan Gosling, Michael Pitt, Agnes Bruckner, Chris Penn
When a pair of bright-but sociopathic teens conspires to commit the perfect murder, a troubled cop teams with her eager new partner to solve the case ... More
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9. Mulholland Falls (1996)
directed by Lee Tamahori
featuring Nick Nolte, Melanie Griffith, Chazz Palminteri, Michael Madsen, Chris Penn
Four men just barely on the right side of the law step into a web of danger and corruption in this drama. In the early 1950s, Max Hoover (Nick Nolte) ... More
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10. Deceiver (1998)
directed by Jonas Pate, Joshua Pate
featuring Tim Roth, Chris Penn, Michael Rooker, Renée Zellweger, Ellen Burstyn
Walter Wayland (Tim Roth) has lead a life that many would envy. The heir to a fortune, he was educated at Princeton and then took over the family ... More
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11. Shelter Island (2003)
directed by Geoff Schaaf
featuring Ally Sheedy, Patsy Kensit, Stephen Baldwin, Mimi Langeland, Chris Penn
Geoff Schaaf's thriller Shelter Island features a couple who have attempted to get away from it all at their vacation home at the place where the ... More
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12. Pale Rider (1985)
directed by Clint Eastwood
featuring Clint Eastwood, Michael Moriarty, Carrie Snodgress, Chris Penn, Richard Dysart
A mysterious and possibly otherworldly stranger comes to the rescue of a frontier town in this Western, which was strongly influenced by the George ... More
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13. The Florentine (1999)
directed by Nick Stagliano
featuring Michael Madsen, Chris Penn, Jeremy Davies, Tom Sizemore, Luke Perry
The regulars at a shot-and-a-beer bar in a decaying working-class town are the focus of Nick Stagliano's drama The Florentine. Michael Madsen plays ... More
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14. Sacred Cargo (1996)
directed by Aleksandr Buravsky
featuring Chris Penn, Martin Sheen, J.T. Walsh, Anna Karin
A man who thinks that he's on a mission of mercy finds himself in the middle of international espionage at its most dangerous in this thriller. ... More
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15. One Tough Cop (1998)
directed by Bruno Barreto
featuring Stephen Baldwin, Chris Penn, Mike McGlone, Gina Gershon, Paul Guilfoyle
Brazilian director Bruno Barreto helmed this Jeremy Iacone screenplay "inspired by" New York detective Bo Dietl's 1988 autobiography, One Tough Cop: ... More
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16. The Boys Club (1996)
directed by John Fawcett
featuring Chris Penn, Dominic Zamprogna, Devon Sawa, Stuart Stone, Jarred Blanchard
Bored small-town teens anxious for excitement get in over their heads when they believe the wild tales of a wounded stranger in this absorbing and ... More
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17. Under the Hula Moon (1995)
directed by Jeff Celentano
featuring Stephen Baldwin, Emily Lloyd, Chris Penn, Musetta Vander, Edie McClurg
In this comedy thriller, a couple living in Cactus Gulch, dream of escaping the desert and moving to Hawaii. Their little house trailer has become a ... More
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18. Best of the Best (1989)
directed by Bob Radler
featuring Eric Roberts, James Earl Jones, Sally Kirkland, Phillip Rhee, Chris Penn
Learning the value of teamwork, the racially diverse U.S. karate team must work through their personal troubles to successfully participate in the ... More
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19. At Close Range (1986)
directed by James Foley
featuring Sean Penn, Christopher Walken, Mary Stuart Masterson, Chris Penn, Millie Perkins
Amazingly, At Close Range was based on a true story. Bored teenager Sean Penn meets his prodigal father (Christopher Walken) for the first time in ... More
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20. The Pickle (1993)
directed by Paul Mazursky
featuring Danny Aiello, Dyan Cannon, Clotilde Courau, Shelley Winters, Barry Miller, Jerry Stiller, Chris Penn, Ally Sheedy
Paul Mazursky directed this comedy, which blends a broad satire of the film industry with a thoughtful tale of a middle-aged man looking back on his ... More
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21. The Funeral (1996)
directed by Abel Ferrara
featuring Christopher Walken, Chris Penn, Vincent Gallo, Annabella Sciorra, Isabella Rossellini, Benicio Del Toro
Cult figure Abel Ferrara directed this dark, emotional tale of life among the criminal underworld, set in the late 1930s. The Tempio Brothers -- Ray ... More
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22. Fist of the North Star (1995)
directed by Tony Randel
featuring Costas Mandylor, Gary Daniels, Malcolm McDowell, Chris Penn, Melvin Van Peebles
Set in a post-WWIII world, this action fantasy centers on the deadly struggle between a great warrior and the villainous overlord who stole the ... More
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23. Stealing Harvard (2002)
directed by Bruce McCulloch
featuring Chris Penn, Dennis Farina, Jason Lee, John C. McGinley, Leslie Mann, Megan Mullally, Richard Jenkins, Tom Green
Two buddies find themselves doing some very wrong things for perfectly right reasons in this broad comedy. John (Jason Lee) is a nice guy who is ... More
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24. Return from the River Kwai (1989)
directed by Andrew V. McLaglen
featuring Timothy Bottoms, Michael Dante, Edward Fox, Chris Penn, George Takei, Nick Tate
This poorly received sequel to the classic 1957 movie The Bridge over the River Kwai, is also based on a true story, as told in the book by Joan & ... More
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25. Short Cuts (1993)
directed by Robert Altman
featuring Andie MacDowell, Bruce Davison, Tim Robbins, Chris Penn, Julianne Moore, Anne Archer, Matthew Modine, Fred Ward, Jack Lemmon, Jennifer Jason Leigh, Lili Taylor, Robert Downey, Jr., Madeleine Stowe, Lily Tomlin, Tom Waits, Frances McDormand, Peter Gallagher, Annie Ross, Lori Singer, Lyle Lovett, Buck Henry, Huey Lewis
Based on stories by Raymond Carver, Short Cuts follows 22 Los Angeles residents whose lives intersect over the course of a few days. Ann and Howard ... More
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