Steve McQueen as Captain Virgil Hilts, The Great Escape (1963)
As an Air Force Captain breaking out of a Nazi prison camp, McQueen leads an impressive cast in this classic World War II epic. Among its other achievements, 'The Great Escape' also offers the iconic image of America's favorite rebel jumping his motorcycle across the barbed-wire border between Germany and Switzerland.
Paul Newman as Luke Jackson, Cool Hand Luke (1967)
Newman never looked quite as, ahem, cool as he does as a rebellious delinquent in this American classic. With his rugged work shirts and a bottle opener dangling coolly around his neck, his relaxed and masculine style is one that will never suffer from a failure to communicate.
Brad Davis as Billy Hayes in Midnight Express (1978)
As a college student arrested for attempting to smuggle hashish out of Turkey, Davis serves as the emotional center of this powerful and wrenching film. His all-American attitude helps keep him sane in prison until he is sentenced to 30 more years, prompting his escape in a guard's uniform.
Clint Eastwood as Frank Morris in Escape from Alcatraz (1979)
Eastwood's gruff visage seems right at home at the wind-whipped facility in the middle of the San Francisco Bay, where prisoners bundle up against the fog in surprisingly stylish pea coats and matching beanies.
Tim Robbins as Andy Dufresne in The Shawshank Redemption (1994)
Playing the sensitive convicted murderer dreaming of Mexico's Zihuatanejo, Robbins’ oversized suits and chambray shirts are just right for evoking the ‘50s and ‘60s.
George Clooney as Ulysses Everett McGill in O Brother, Where Art Thou? (2000)
The always on-point Clooney looks as good as ever in the Coen Brothers' Depression-era rewrite of The Odyssey. The fast-talking mastermind makes the best out of a baggy striped shirt and a pair of denim overalls, but it's his perfectly-coiffed hair that takes the cake, held in sleek place with a never-ending supply of Dapper Dan pomade.
Wentworth Miller as Michael Scofield in Prison Break (2005-2009)
Tattoos may be everywhere these days, but few are simultaneously stylish and practical like the ones covering Miller's upper body in this dark Fox drama (they serve as the blueprints for his attempt to break out his incarcerated brother). A tight crew cut adds the finishing touch to his menacing look.
Buzz Lightyear (voice of Tim Allen), Toy Story 3 (2010)
Thanks to a mismanaged hard reset, everyone's favorite toy astronaut gets a little Latin flair in the third outing of the beloved Toy Story series. Spouting Spanish, the spaceman finally tangoes his way into Jessie's heart as the gang escapes from Sunnyside Daycare. In the process, he proves that the right moves can overcome even the clunkiest of outfits.
Honorable Mentions: Harrison Ford as Dr. Richard Kimble in The Fugitive (1993), John Malkovich as Cyrus Grissom in Con Air (1997), Jim Caviezel as Edmond Dantès in The Count of Monte Cristo (2002)
Photo Credit: The Mirsch Corporation, Corbis, Casablanca Film Works, Castle Rock Entertainment, Touchstone/Universal Pictures, Adelstein-Parouse Productions, Disney/Pixar