Once again, maybe I wasn't looking hard enough, but I was surprised to not find an existing thread for this. Correct me if I'm wrong.
Mine are...
MALE
Marlon Brando in LAST TANGO IN PARIS (1972)
Leonardo DiCaprio in REVOLUTIONARY ROAD (2008)
David Thewlis in NAKED (1993)
Robert De Niro in RAGING BULL (1980)
Al Pacino in DOG DAY AFTERNOON (1975)
Gregory Peck in TO KILL A MOCKINGBIRD (1962)
River Phoenix in MY OWN PRIVATE IDAHO (1991)
James Dean in EAST OF EDEN (1955)
Peter Lorre in M (1931)
Orson Welles in CITIZEN KANE (1941)
FEMALE
Ellen Burstyn in REQUIEM FOR A DREAM (2000)
Bette Davis in WHAT EVER HAPPENED TO BABY JANE? (1962)
Audrey Hepburn in BREAKFAST AT TIFFANY'S (1967)
Naomi Watts in 21 GRAMS (2003)
Kate Winslet in REVOLUTIONARY ROAD (2008)
Diane Keaton in ANNIE HALL (1977)
Ellen Page in THE TRACEY FRAGMENTS (2007)
Elizabeth Taylor in WHO'S AFRAID OF VIRGINIA WOOLF? (1966)
Faye Dunaway in BONNIE AND CLYDE (1967)
Kim Novak in VERTIGO (1958)
Mine are...
MALE
Marlon Brando in LAST TANGO IN PARIS (1972)
Leonardo DiCaprio in REVOLUTIONARY ROAD (2008)
David Thewlis in NAKED (1993)
Robert De Niro in RAGING BULL (1980)
Al Pacino in DOG DAY AFTERNOON (1975)
Gregory Peck in TO KILL A MOCKINGBIRD (1962)
River Phoenix in MY OWN PRIVATE IDAHO (1991)
James Dean in EAST OF EDEN (1955)
Peter Lorre in M (1931)
Orson Welles in CITIZEN KANE (1941)
FEMALE
Ellen Burstyn in REQUIEM FOR A DREAM (2000)
Bette Davis in WHAT EVER HAPPENED TO BABY JANE? (1962)
Audrey Hepburn in BREAKFAST AT TIFFANY'S (1967)
Naomi Watts in 21 GRAMS (2003)
Kate Winslet in REVOLUTIONARY ROAD (2008)
Diane Keaton in ANNIE HALL (1977)
Ellen Page in THE TRACEY FRAGMENTS (2007)
Elizabeth Taylor in WHO'S AFRAID OF VIRGINIA WOOLF? (1966)
Faye Dunaway in BONNIE AND CLYDE (1967)
Kim Novak in VERTIGO (1958)
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I was recently in an independent comedy-drama about post-high school indecision. It's called Generation Why.
See the trailer here: