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James Dunn — 1946
A Tree Grows in Brooklyn (1945)
Elia Kazan’s first feature film, and he’s already directing people to Academy Awards! James Dunn played Johnny Nolan, one of the film’s broad canvas of striving Irish Americans in Williamsburg. Today, that’s a neighborhood that specializes in art galleries and gyms that offer ayahuasca experiences.
Barry Fitzgerald — 1945
Going My Way (1944)
Going My Way was a huge hit in 1945, winning best picture, best director for Leo McCarey, best actor for Bing Crosby, and several other awards. The film also won Barry Fitzgerald the supporting-actor prize for his turn as Father Fitzgibbon, an old-fashioned priest in this generation gap musical comedy. Weird footnote: Oscar voting was still sorting itself out back then, and Fitzgerald was also nominated for best actor for this same part—a one-time fluke. This film gave us Bing’s recording of one of his signature tunes, “Swinging on a Star,” which won an Oscar and is listed in the Grammy Hall of Fame despite being (forgive me, Bing, I love you) one of the most annoying songs in the history of music.
Charles Coburn — 1944
The More the Merrier (1943)
Charles Coburn beat out Claude Rains in Casablanca, which might be ne plus ultra of a performance for a best-supporting-actor Oscar. Criminal! (And worse, Rains would be nominated in this category four times in total, but would never win.) Anyhow, The More the Merrier, a zany look at unlikely housemates during the WWII housing shortage, was also nominated for best picture, and George Stevens was nominated for best director.
Van Heflin — 1943
Johnny Eager (1941)
Van Heflin (later beloved by Jasper on The Simpsons) took home the Oscar for best supporting actor for his turn in Mervyn LeRoy’s sleazy noir Johnny Eager. Heflin plays a philosophizing drunk and best pal to Robert Taylor’s titular Johnny, who runs a crime syndicate facing a crisis. The brassy score was composed by the great Bronislaw Kaper, who also composed the jazz standard “On Green Dolphin Street.”
Donald Crisp — 1942
How Green Was My Valley (1941)
John Ford’s sweeping Welsh family epic is best remembered these days for being the movie that, bafflingly, in retrospect, won best picture over Citizen Kane. But don’t let that steer you away from checking out the film, led by Walter Pidgeon, Maureen O’Hara, and a young Roddy McDowall. Donald Crisp’s Gwilym Morgan is a hardworking coal miner doing his best to provide for his family during a time of unease. He also beat Walter Brennan this year—who, as we will soon see, didn’t need any more best-supporting-actor Oscars at this point.
Walter Brennan — 1941
The Westerner (1940)
And here comes Walter Brennan, the Michael Jordan of the Academy Award for best supporting actor—the category’s only three-time winner. His final win in The Westerner (beating Jack Oakie as a thinly-veiled Benito Mussolini in The Great Dictator) is a great villain performance of the power-mad Judge Roy Bean (“the only law west of the Pecos”) opposite the righteous Gary Cooper. The true-life character would be revived 32 years later by Paul Newman in The Life and Times of Judge Roy Bean.
Thomas Mitchell — 1940
Stagecoach (1939)
John Ford’s Western masterpiece Stagecoach was nominated for seven Oscars, but only won two—for Thomas Mitchell’s best supporting actor turn, and best scoring. (John Wayne didn’t even get nominated! Why I oughta sock someone in the jaw and spit tobacco on the floor!) Mitchell played a drunken physician (“Doc”), one of many passengers on a treacherous journey through Apache country.
Walter Brennan — 1939
Kentucky (1938)
Walter Brennan’s second win as best supporting actor was for the horse racing romantic drama Kentucky. (Now the title makes sense.) There are 50 states in the United States of America, and more than you may think have lent their names for the titles of motion pictures. Sure, there’s the classic musical Oklahoma!, the James A. Michener adventure Hawaii, and the Jennifer Jason Leigh vehicle Georgia, but I find it amusing that in 1940 some young gentleman may have been on a first date when he told a ticket-seller, “Two for Maryland, please.”
Joseph Schildkraut — 1938
The Life of Emile Zola (1937)
The Austrian actor Joseph Schildkraut won the second-ever Oscar for best supporting actor for the part of Captain Alfred Dreyfus in The Life of Emile Zola. Dreyfus, of course, was at the center of “The Dreyfus Affair,” a French controversy that inspired movies as early as 1899 (by Georges Méliès) and as recently as 2019 (by Roman Polasnki), with José Ferrer and Ken Russell (among others) in between.
Walter Brennan — 1937
Come and Get It (1936)
The ninth Academy Awards were the first ceremony to include best supporting actor and best supporting actress—and Walter Brennan, who won it three times, will always be remembered as the granddaddy of the category. Come and Get It, a rags-to-riches story about lumberjacks (the ’30s!), was codirected by William Wyler and Howard Hawks. Wyler directed Brennan to his win in The Westerner, so this makes Christoph Waltz and Quentin Tarantino the only solo director-and-performer double-winners in this category. Hooray!
Has anyone ever won best actor and best supporting actor?
Yes! Jack Nicholson has two best-actor statuettes and one best-supporting-actor Oscar. Denzel Washington has one Oscar in each category, as do Jack Lemmon, Robert De Niro, Gene Hackman, and Kevin Spacey.
Who has the most Oscars?
Walt Disney has the most Oscars of any individual, with 26 trophies to his name (22 competitive Oscars 4 honorary awards), while Katharine Hepburn is the most decorated performer in the history of the Oscars (she won best actress four times). The most decorated supporting actor in Oscar history is Walter Brennan, who won in that category three separate times—for Come and Get It (1936), Kentucky (1938), and The Westerner (1940). He was also the very first actor to win in this category.
Who is the only person to receive two Oscars for the same role in the same film?
Harold Russell, who won both an honorary award and the competitive award for best supporting actor in 1947 for his performance in The Best Years of Our Lives.
Who is the youngest person to win the Oscar for best supporting actor?
Timothy Hutton, who was just 20 years old when he won best supporting actor for Ordinary People in 1981.