It’s the role...it’s the role
The following roles have proven to be rewarding for the actors who’ve
played them as the role has been nominated for Oscars...at least twice.

"Vicki Lester" earned both Janet Gaynor and Judy Garland nominations in this A Star is Born lead part. Unfortunately, the role didn’t help Barbra Streisand. Maybe it was the name.

"Arthur Chipping". For both Peter O’Toole and Robert Donat, this lead role in Goodbye, Mr. Chips earned nominations but Donat won...O’Toole didn’t (in fact, O’Toole has lost all 7 of his nominations)

"Vito Coreleone". Two of the film industry’s greatest stars, Marlon Brando and Robert De Niro, were both nominated for this Godfather role. How great is the role? How great are they? Both won.

"Joe Pendleton"- Robert Montgomery played in Here Comes Mr. Jordan in 1941 and the role was reprised by Warren Beatty in Heaven Can Wait in 1978. Both went home empty handed.

"Max Corkle"- The supporting roles in Here Comes Mr. Jordan and Heaven Can Wait played by James Gleason and Jack Warden, respectively, didn’t fare much better.

"Henry VIII" Three actors played this oft-married character. Charles Laughton won for The Private Life of Henry VIII. Robert Shaw (A Man for All Seasons) and Richard Burton (Anne of A Thousand Days) didn’t fare as well.

But it’s not always different actors playing the roles. Sometimes the same actor played the role twice...to mixed results.

"Henry II"- Peter O’Toole played this character twice. Once in Beckett (1964) and again in The Lion in Winter (1968). Did he win? We already told you...O’Toole never won.

"Fast Eddie Felson" Paul Newman played him young in The Hustler in 1961. He played him a bit more aged in The Color of Money 25 years later. Oscar voters liked the older version better.

"Father O’Malley" Bing Crosby played this character twice, just one year apart. In 1944, he starred in Going My Way and followed it with The Bells of St. Mary. They liked him better the first time.

"Michael Coreleone"- Al Pacino played this character three times in the Godfather trilogy. He was nominated the first two times...and lost. Perhaps the voters were tired of him by the third as he wasn’t even nominated.