Matt Damon as Mike McDermott

Edward Norton as Lester 'Worm' Murphy

John Turturro as Joey Knish

Gretchen Mol as Jo

John Malkovich as Teddy KGB

Famke Janssen as Petra

Martin Landau as Abe Petrovsky

Michael Rispoli as Grama

Goran Višnjić as Maurice

Mal Z. Lawrence as Irving

Paul Cicero as Russian Thug

Ray Iannicelli as Kenny

Merwin Goldsmith as Sy

Sonny Zito as Tony

Josh Mostel as Zagosh

Lenny Clarke as Savino

Peter Yoshida as Henry Lin

Jay Boryea as Russian Thug #2

Lenny Venito as Moogie

Richard Mawe as Professor Eisen

Michael Lombardi as D.A. Shields

Tom Aldredge as Judge Marinacci

Beeson Carroll as Judge Kaplan

E. Matthew Yavne as Professor Green

Erik LaRay Harvey as Roy

Dominic Marcus as Dowling

Brian Anthony Wilson as Derald

George Kmeck as Prison Guard

Joseph Parisi as Property Guard

Melina Kanakaredes as Barbara

Kohl Sudduth as Wagner

Charlie Matthes as Birch

Hank Jacobs as Steiny

Chris Messina as Higgins

Michael Ryan Segal as Griggs

Kerry O'Malley as Kelly

Slava Schoot as Roman

Michele Zanes as Taj Dealer

Allan Havey as Guberman

Joey Vega as Freddy Face

Neal Hemphill as Claude

Vernon E. Jordan Jr. as Judge McKinnon

Johnny Chan as Johnny Chan

Lisa Gorlitsky as Sherry

John Di Benedetto as LaRossa

Nicole Brier as Sunshine

Tony Hoty as Taki

Mario Mendoza as Zizzo

Joe Zaloom as Cronos

Sal Richards as Johnny Gold

Josh Pais as Weitz

Adam LeFevre as Sean Frye

P.J. Brown as Vitter

David Zayas as Osborne

Michael Arkin as Bear

Murphy Guyer as Detweiler

Alan Davidson as Cabbie

Bill Camp as Eisenberg

Maria Soccor as Atlantic City Call Girl (uncredited)