Quiz: Can You Match the Actor to Their Oscar-Winning Role?

Do you consider yourself an Oscars know-it-all? This quiz should help you put it to the test. Given how many great actors have received this accolade over the almost-hundred-year history of the award show, it’s easy to forget and lose track, especially when it comes to actors who have won the prestigious award more than once. 

Many winners have used the platform to bring attention to greater issues, like when Sacheen Littlefeather went on stage to reject Marlon Brando’s Oscar win on his behalf in 1973, highlighting the mistreatment of Native Americans by Hollywood. 

The Oscars have had their fair share of awkward moments, too, like the Moonlight/La La Land mix-up in 2017. And who can forget Joe Pesci’s short and iconic speech after winning the award? 

Some actors have also racked up quite an achievement in this category, like Lupita Nyong’o winning an Oscar for her first movie ever, 12 Years a Slave. Or Tom Hanks winning two Oscars back to back for Philadelphia (1993), and then Forrest Gump (1994). 

The Most Winning Actors in Oscar History

Winning just one Oscar is a pretty substantial accomplishment, but there have been plenty of actors who have gone on to win two, three, or even four Oscars for their acting roles. On the flip side, some actors have refused to accept their winning Oscar, and sometimes, refused to even be nominated. 

Katharine Hepburn remains the actor with the most Oscars at four. Nobody else has beaten that record, even after all these years. Funnily enough, she skipped all four of the ceremonies where she won the award, believing that they were “silly.” 

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Meryl Streep is right behind her in terms of wins. She has three wins, but she’s also the most nominated actor in history with 21 nominations. Then you have Jack Nicholson, also with three wins, and he’s the most nominated male actor ever, with 12 nominations.

Daniel Day-Lewis also has three wins. He retired from acting in 2017, but came out of retirement for Anemone (2025), which was directed by his son. 

Frances McDormand also has three acting Oscars, two of those being relatively recent. She won two Oscars in 2021 for Nomadland (2020), one as an actor and one as a producer for the movie.