Josh Brolin and Chris Penn in The Young Riders (1989)

Chris Penn, Gary Carlos Cervantes, and Luis Contreras in Under the Hula Moon (1995)

Steve Buscemi, Harvey Keitel, Quentin Tarantino, Michael Madsen, Tim Roth, Chris Penn, Edward Bunker, and Lawrence Tierney in Reservoir Dogs (1992)

Robert Downey Jr., Jennifer Jason Leigh, Lili Taylor, and Chris Penn in Short Cuts (1993)

Kevin Bacon and Chris Penn in Footloose (1984)

Kevin Bacon, Sarah Jessica Parker, Chris Penn, Elizabeth Gorcey, Kim Jensen, and John Laughlin in Footloose (1984)

Steve Buscemi, Quentin Tarantino, Michael Madsen, Chris Penn, Edward Bunker, and Lawrence Tierney in Reservoir Dogs (1992)

Harvey Keitel, Tim Roth, Chris Penn, and Lawrence Tierney in Reservoir Dogs (1992)

Michael Madsen, Nick Nolte, Chazz Palminteri, and Chris Penn in Mulholland Falls (1996)

Chris Penn, Lori Singer, and Adrian Pasdar in Made in U.S.A. (1987)

Chris Penn and Adrian Pasdar in Made in U.S.A. (1987)

Renée Zellweger, Tim Roth, Chris Penn, and Michael Rooker in Deceiver (1997)

Gina Gershon, Stephen Baldwin, and Chris Penn in One Tough Cop (1998)

Stephen Baldwin, Emily Lloyd, and Chris Penn in Under the Hula Moon (1995)

Steve Buscemi, Harvey Keitel, Quentin Tarantino, Michael Madsen, Tim Roth, and Chris Penn in Reservoir Dogs (1992)

Martin Sheen, J.T. Walsh, Chris Penn, and Anna Karin in Sacred Cargo (1995)

Jennifer Connelly, Michael Madsen, Nick Nolte, Chazz Palminteri, and Chris Penn in Mulholland Falls (1996)

Chris Penn, Gary Daniels, and Costas Mandylor in Fist of the North Star (1995)

Sherilyn Fenn, Henry Czerny, Chris Penn, Anthony DeSando, and Jeffrey Wright in Cement (2000)

Eric Roberts, Chris Penn, John Dye, David Agresta, and Phillip Rhee in Best of the Best (1989)