Competing Against His Best Friend
In 1941, Stewart hit the jackpot with The Philadelphia Story, a movie that landed him an Oscar. He shared the screen with big shots like Katharine Hepburn and Cary Grant. It was a big deal, and he walked away with the golden trophy at the Academy Awards.

You’d think winning an Oscar would be the highlight of his career, right? Well, mostly yes, but there’s a twist. Stewart was up against his buddy Henry Fonda for the award. Stewart voted for Fonda to win because he is the good guy he is. Tough luck for him, but a true friend move!