Random thoughts on a series of Oscar “what-ifs”:
1939—Jimmy Stewart should have won for Mr. Smith Goes to Washington or maybe Clark Gable for Gone with the Wind. The winner that year was Robert Donat for Goodbye, Mr. Chips in a performance that hasn’t aged that well. Stewart won an unearned Oscar for The Philadelphia Story the next year as a consolation prize, which robbed Henry Fonda of his deserved award for The Grapes of Wrath. Fonda had to wait until 1982 for his award for On Golden Pond.

1943—The winner was Paul Lukas, a prestige performance in a prestige film, Watch on the Rhine. The award should have done to Humphrey Bogart for Casablanca, a performance which had indeed aged well. But if he’d won that year, he likely wouldn’t have gotten his career award for The African Queen (see 1951).

1948—The winner was Laurence Olivier for Hamlet. The Treasure of the Sierra Madre won Best Supporting Actor for Walter Huston, but Humphrey Bogart wasn’t even nominated for Best Actor in what many consider his best performance. But if he’d won that year, he (again) likely wouldn’t have gotten his career award for The African Queen…
1951…and if Bogart had gotten an Oscar earlier for Casablanca or Sierra Madre, Marlon Brando may well have won a well-deserved award for A Streetcar Named Desire…
1954…which might have prevented Brando from winning for On the Waterfront (a sad thought) He might have done a Bette Davis and won two awards in proximity (Dangerous and Jezebel). But then the award, assuming Bogart hadn’t already received one at this pooint, might have finally gone to him for The Caine Mutiny. Since by 1954, Bogart, Brando, and Bing Crosby already had Oscars, if Brando hadn’t won for Streetcar, the award might have gone to another deserving performance, that of James Mason in the problematic A Star is Born…

And speaking of, not awarding Judy Garland for that film is the worst Oscar non-win in its history, not only because of her great performance, but because winner Grace Kelly (The Country Girl) didn’t rise to the occasion (she was, as they say, “fine”). But turning gorgeous into dowdy and older is always catnip for the Academy, and the industry was in love with Kelly pretty much upon her arrival. Plus, A Star is Born had a lot of production problems, many tracing back to Garland herself. Still, a huge miss.

1974—If Al Pacino had won the Oscar for The Godfather, Part II, he most certainly wouldn’t have won his career/consolation prize for 1992’s Scent of a Woman, and Denzel Washington would likely have won for Malcolm X.

Lastly, if Mary Pickford (Coquette) Roberto Begnini (Life is Beautiful) and Will Smith (King Richard) hadn’t won Oscars…the world might be a better place.