Despite a reputation as one of the most talented actors from Hollywood’s Golden Age, James Stewart only had one movie win an Oscar.The Philadelphia Storymay not be the legendary actor’s most famous film or even one made during the height of his acting career, but it is still regarded as one ofJames Stewart’s best movies, as it currently holds a 100% rating on Rotten Tomatoes.

Usually as the lead, James Stewart is associated with a long list of Hollywood classics, across a variety of genres. Perhaps the film he’s most widely recognized for isIt’s a Wonderful Life, the 1946 Christmas favorite he starred in alongside Donna Reed. But it’s hardly the only James Stewart movie to reach icon status, as there’s also Alfred Hitchcock’sRear Window,Mr. Smith Goes to Washington, andAnatomy of a Murder. For many of these, Stewart unsurprisingly achieved critical acclaim, but out of them all,onlyThe Philadelphia Storywon him the industry’s top award.

Katharine Hepburn and her suitors James Stewart and Carey Grant in The Philadelphia Story

The Philadelphia Story Was James Stewart’s Only Oscar Win

James Stewart Beat Out Henry Fonda At The Academy Awards

Over the years, Stewart accumulated multiple Oscar nominations, with his first coming in 1939 when he played the titular character inMr. Smith Goes to Washington.He received another just a year later when he appeared inThe Philadelphia StorywithKatharine Hepburn and Cary Grant, a romantic comedy directed by George Cukor. In the movie, Stewart played Mike Connor, one of three love interests for Hepburn’s Tracy. Mike is a reporter who competes with two other men for Tracy’s affections (including her fiance).

All three of the leads received considerable praise for their performances in the film, with Stewart and Hepburn getting nominated for Best Actor and Best Actress respectively. But Stewart was ultimately the only cast member to win. More nominations followed in subsequent years, with Stewart also getting recognition for his roles inIt’s a Wonderful Life, Harvey, and Anatomy of a Murder.But like what happened withMr. Smith Goes to Washington,Stewart saw his competition win each time andnever won a second Oscar for any of his films.

The Grapes of Wrath (1940)

Why James Stewart Thought Another Actor Should Have Won Best Actor In 1940

James Stewart Never Thought Mike Conner Was His Best Performance

BecauseThe Philadelphia Storywas an important milestone for James Stewart and one that he never repeated, it’s all the more interesting that the actor seemingly didn’t think his work in the film was Oscar-worthy. He admitted as much in his acceptance speech, telling the audience that he hadactually cast his Best Actor vote not for himself but for Henry Fonda, who had turned in an extremely memorable performance inThe Grapes of Wrath.

Though it’ll never be confirmed one way or another, there was a sentiment at the time - that persists to this day - that Stewart’s Oscar win was an effort to rectify his snub in 1939, when he failed to win it forMr. Smith Goes to Washington. With Mike Conner essentially being a supporting role inThe Philadelphia Storyand Grant being the real male lead, it did seem odd that out of all the movies he made, this was one that got him the ever-elusive award.

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The Philadelphia Story

Cast

A wealthy woman learns the truth about herself when her ex-husband and a tabloid reporter show up just before her planned remarriage.