They’re screen legends who made classic, hit films, but the one thing that eluded them was Hollywood’s highest honor: an Academy Award for acting.
Though popular with audiences from the 1930s through the ‘50s in hits like His Girl Friday, North by Northwest, and Bringing Up Baby, Grant never won an Oscar. He was only nominated twice, for Penny Serenade and None But the Lonely Heart.
While Astaire was known primarily for his dancing, he was one of the biggest screen draws in the mid-20th century. While his frequent on-screen dance partner Ginger Rogers won an Oscar for her dramatic turn in Kitty Foyle (1940), Astaire was only nominated once, and sentimentally toward the end of his career for Best Supporting Actor for his role in the 1974 disaster movie The Towering Inferno.
Garland successfully transitioned from child star to adult fame and enjoyed a stage and recording career, too. She never won a Best Actress Oscar, though, although she was nominated once for A Star is Born and in the supporting category for Judgment at Nuremberg. In 1962, however, Garland was honored with a lifetime achievement Oscar—at 39 years old, the youngest person to ever receive the award.
Kelly starred in three of the most popular and critically acclaimed movie musicals of all time: Anchors Aweigh, An American in Paris, and Singin’ in the Rain. His direction and choreography of movie musicals defined the genre, and yet Kelly never won an Oscar for his performance. He was nominated for acting only once, for Anchors Aweigh.
Perhaps the most enduringly popular screen icon of all time, Monroe never won an Academy Award. Nor was she ever nominated for one.