Published On: Sun, Mar 15th, 2026
Entertainment | 2,157 views

The biggest Oscar upsets ever from Grace Kelly to Saving Private Ryan | Celebrity News | Showbiz & TV

Now just two years shy of it’s 100th anniversary the Oscars have given out over 3,000 awards over the decades. They are voted on by members of the Academy of Motion Picture Arts and Sciences and it is widely accepted the glitzy Hollywood ceremony honours the best of the year’s work in the motion picture industry.

But sometimes they throw a curveball and there have been several upsets over the years. From films with multiple nominations winning nothing to shoo-ins in the acting categories walking away empty handed. Some of these upheavels have become the stuff of legend and are still debated years later. While there may have been fewer of these moments in recent years, it is always still a possibilty and it is this unpredictability which makes the show such an enticing watch. We won’t jinx any of this year’s nominees by speculating if there could be an upset in their category but here are a few of the most famous historical wins (or losses) that no one saw coming.

1955 – Grace Kelly beats Judy Garland to the Oscar

Split image close ups of Grace Kelly and Judy Garland

Judy Garland seemed set to win an Oscar for, A Star is Born, that although she couldn’t attend – she had just given birth to her son Joey –  a camera crew was sent to her hospital room to capture the moment. Instead, she lost to Grace Kelly for Country Girl in an upset comedian and actor, Groucho Marx, described as “the biggest robbery since Brinks”.

(Image: Getty)