While it may come as a shock that big names like Glenn Close, Ian McKellen, and Angela Bassett have never brought home an Oscar, even more surprising are some of the stars who do have that coveted statuette on their shelves. Some of these wins may be unexpected because you know the star best from a different field, while others seem less likely because of the kind of art that celebrity makes. From a rapper who's been denounced by members of Congress to an actor who plays one of the most outrageous characters on the cult hit sitcom Community, here are eight stars you probably didn’t realize have won Academy Awards.
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1 | Eminem
Dimitrios Kambouris/Getty ImagesWhen “Lose Yourself,” from the semi-autobiographical film 8 Mile, became the first hip-hop track to win an Academy Award for Best Original song in 2003, Eminem, who also starred in a loose version of his life story, was nowhere to be found. The artist (real name: Marshall Mathers) had stayed home, leaving collaborator Luis Resto to accept the award from presenter Barbara Streisand. Seventeen years later, Eminem performed the song at the 2020 Oscars and explained his earlier absence to Variety. “Back then, I never even thought that I had a chance to win, and we had just performed ‘Lose Yourself’ on the Grammys with the Roots a couple of weeks before the Oscars, so we didn’t think it was a good idea," he said. "And also, back at that time, the younger me didn’t really feel like a show like that would understand me.”
2 | Kobe Bryant
FeatureFlash Photo Agency/ShutterstockIn 2018, the late Kobe Bryant’s film Dear Basketball won the Best Animated Short Film at the Oscars. The film is based on the poem the iconic player wrote upon announcing his retirement from the NBA in 2015 and featured music by composer John Williams. “As basketball players, we’re supposed to just shut up and dribble,” Bryant said in his speech, referencing FOX News host Laura Ingraham’s comments criticizing players who made political statements, according to Sports Illustrated. “I am glad we did a little more than that.”
3 | Bob Dylan
Michael Kovac/WireImageAlmost as surprising as Bob Dylan’s Nobel Prize win (he won in the Literature category in 2016 “for having created new poetic expressions within the great American song tradition") is the bard from Minnesota’s 2001 Oscar win. The singer-songwriter was awarded the Academy Award for Best Original Song for "Things Have Changed" from the 2000 Michael Douglas film Wonder Boys. The trophy made him just the second person (alongside playwright George Bernard Shaw) to hold both a Nobel Prize and Academy Award.
4 | Bret McKenzie
Jaguar PS/ShutterstockOne half of the musical comedy duo Flight of the Conchords, Bret McKenzie won an Oscar in 2012 for the song "Man or Muppet" from the 2011 film, The Muppets. The New Zealander had also served as music supervisor for the film, composing four of its five songs, a role he reprised on the 2014 sequel Muppets Most Wanted. Among the many McKenzie thanked in his acceptance speech was the late Jim Henson.
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5 | Jim Rash
John Shearer/WireImageWhile you may recognize him as the actor who played Dean Craig Pelton on Community from 2009 to 2015, Jim Rash is also part of a screenwriting duo with writing partner, Nat Faxton (also an actor). The two co-wrote the screenplay for the 2011 George Clooney film The Descendants, which was nominated for five Oscars and won the Academy Award for Best Adapted Screenplay. (The pair also co-wrote and co-directed the 2013 coming-of-age film The Way, Way Back.)
6 | Peter Capaldi
Fred Duval/ShutterstockDon’t remember the time the Doctor won an Oscar for It’s a Wonderful Life? The year was 1995, and it was for the short film Franz Kafka's It's a Wonderful Life, specifically. Long before he starred in The Thick of It or stepped foot into the TARDIS on Doctor Who, Scottish actor Peter Capaldi took home the Academy Award for Best Short Film (Live Action) for writing and directing the melodramatic piece starring Withnail and I actor (and occasional Doctor Who guest star) Richard E. Grant.
7 | Oprah Winfrey
Alberto E. Rodriguez/WireImageOprah Winfrey was nominated for Best Supporting Actress for her 1986 performance in The Color Purple and saw 2009’s Precious: Based on the Novel ‘Push’ by Sapphire, which she co-produced, win two awards. In 2011, Winfrey got one of her own, when she was awarded the Jean Hersholt Humanitarian Award, an honorary Oscar for philanthropic work that put her alongside fellow honorees Audrey Hepburn, Quincy Jones, and Paul Newman.
8 | Sam Smith
Gareth Cattermole/Gareth Cattermole/Getty ImagesWhen English singer-songwriter Sam Smith won the 2016 Academy Award for Best Original Song for the James Bond ballad “Writing’s on the Wall” from Spectre (2015), they made headlines—and not just for upsetting an expected win for Lady Gaga. In their acceptance speech, Smith erroneously cited a quote from Ian McKellen about the lack of openly gay Best Actor winners, stating that they may have been the first openly gay man to win an Oscar. (Smith began publicly identifying as non-binary in 2019). While Oscar-winning Milk screenwriter Dustin Lance Blackhad a few things to say about that, McKellen simply stated the facts and congratulated Smith on Twitter, according to Entertainment Weekly.
