Suggestions by @teeyutes
1,374 suggestions

Jack Nicholson
as 1960s in What Actors Could've Played Will Hunting in Various Decades?

Peter O'Toole
as Rolf Gruber in The Sound of Music (1955)

Peter O'Toole
as George Banks in Mary Poppins (1974)

Peggy Lipton
as Gretchen Van Horn in Sabrina (1974)

Terence Hill
as David Larrabee in Sabrina (1974)

Joy Harmon
as Silent Generation in Most Beautiful by Generation

Andrea Dromm
as The most beautiful actresses in Classic Beauty

Charmian Carr
as Silent Generation in Most Beautiful by Generation

Cecil Kellaway
as Dr. Bradley in The Man Who Came To Dinner (1972)

Gregory Peck
as 1950's in Actors who could play Batman in various different decades

Michael Caine
as Beverly Carlton in The Man Who Came To Dinner (1972)

Glynis Johns
as Daisy Stanley in The Man Who Came To Dinner (1972)

Burgess Meredith
as Admiral Boom in Mary Poppins (1974)

José Ferrer
as Sheridan Whiteside in The Man Who Came To Dinner (1972)

Faye Dunaway
as Maggie Cutler in The Man Who Came To Dinner (1972)

Lesley Ann Warren
as Lorraine Sheldon in The Man Who Came To Dinner (1972)

Mel Brooks
as Banjo in The Man Who Came To Dinner (1972)

Ingrid Bergman
as Sarah Brady in Inherit The Wind (1980)

Jack Nicholson
as Charlie Allnut in Humphrey Bogart Recast

Jack Nicholson
as E. K. Hornbeck in Inherit The Wind (1980)