It took awhile for the motion picture industry to take comedy seriously enough to give it the Oscar respect that it deserved. It wasn’t until James Stewart won the Best Actor Oscar for “The Philadelphia Story” in 1941 that Hollywood finally gave some official love to a comedic performance. Not coincidentally, the film is considered one of the best romantic comedies of all time.
To determine the comedic performances that won Oscars, 24/7 Tempo reviewed data on Oscars history from the Academy Awards Database of the Academy of Motion Picture Arts and Sciences, considering movies tagged as “comedy” on IMDb, an online movie and TV database owned by Amazon. Performances are in chronological order.
Even after Stewart’s Oscar, the entertainment industry was slow to award the golden statue for comedic star turns. That began to change in the late 1960s. Walter Matthau, who appeared in four motion pictures on the list, won as Best Supporting Actor for “The Fortune Cookie” (1966), in which he co-starred with Jack Lemmon. (The film was the first of 10 comedic film pairings of Matthau and Lemmon.)
Actors and actresses won Academy Awards for three movies written by playwright and screenwriter Neil Simon in the 1970s – “California Suite,” “The Goodbye Girl,” and “The Sunshine Boys.” (These are the biggest all-time Academy Award winners.)
Performers won five Oscars for motion pictures directed by Woody Allen that appear on the list, starting in the late 1970s. Two of those awards went to Dianne Wiest, who won for “Bullets Over Broadway” and “Hannah and Her Sisters.” Speaking of that film, it also won an Oscar for Michael Caine’s performance.
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