“Succession” star Kieran Culkin is poised to make the journey from the Emmys to the Oscars thanks to his role in the red-hot film, “A Real Pain.” From Searchlight Pictures, “A Real Pain” is written and directed by actor Jesse Eisenberg, who made his debut as writer-director in 2022 with the acclaimed “When You Finish Saving The World.” This one follows Eisenberg and Culkin as a pair of mismatched cousins who tour through Poland in an attempt to honor their grandmother. Their journey is threatened to be derailed, however, when old tensions and family history, rear their head once more.
The trailer for the film promises a smart, witty comedy-drama that seems perfect for the quick-fire delivery styles of both Eisenberg and Culkin. Culkin, in particular, could really shine here in his role as Benji Kaplan. In fact, we are so excited about this film that Culkin is currently in our (very early) top five predictions for Best Supporting Actor in our Oscars odds chart. Our predicted nominees at this time of writing are Samuel L. Jackson (“The Piano Lesson”), Clarence Maclin (“Sing Sing”), Culkin, Stanley Tucci (“Conclave”), and Denzel Washington (“Gladiator II”).
This would be Culkin’s first-ever Oscar nomination, although he is no stranger to awards. He played Roman Roy in HBO’s smash drama series “Succession,” a role which brought the actor three Emmy nominations. He was recognized for Best Drama Supporting Actor in 2020 and 2022 and then won Best Drama Actor in 2024. The show was a mammoth hit and showcased Culkin’s searing talent. This could be the perfect Oscars tee-up for the actor. This has happened before, too.
Laura Dern won Best TV Movie/Limited Series Supporting Actress in 2017 for the beloved “Big Little Lies” before she went on to win Best Supporting Actress for “Marriage Story” at the 2020 Oscars. “Big Little Lies” showcased Dern’s talent and then she played a somewhat similar role in “Marriage Story.” Culkin could be in the same vein here with “Succession” and “A Real Pain.”
There have been a number of other thespians who have won Oscars after winning Emmys including:
Rami Malek won Best Drama Actor in 2016 for “Mr. Robot” before he took home the Oscar for Best Actor in 2019 for “Bohemian Rhapsody.”
Julianne Moore won Best TV Movie/Limited Series Actress in 2012 for “Game Change” and then won Best Actress at the 2015 Oscars for “Still Alice.”
Regina King took home Best TV Movie/Limited Series Supporting Actress in 2015 and 2016 for “American Crime” before she also won the Emmy for Best TV Movie/Limited Series Actress for “Seven Seconds” in 2018. She then won Best Supporting Actress at the 2019 Oscars for “If Beale Street Could Talk.”
Halle Berry won Best TV Movie/Limited Series Actress for “Introducing Dorothy Dandridge” in 2000 and then won Best Actress in 2001 for “Monster’s Ball.”
Robin Williams won Best Performance in a Variety or Music Program in 1987 for “Carol, Carl, Whoopi and Robin” and 1988 for “ABC Presents A Royal Gala.” He then won Best Supporting Actor for “Good Will Hunting” in 1998.
And the great Anthony Hopkins took home Best TV Movie/Limited Series Actor in 1976 for “The Lindbergh Kidnapping Case” and in 1981 for “The Bunker.” Hopkins won Best Actor in 1992 for “The Silence of the Lambs” and then claimed his second Best Actor in 2021 — for “The Father.”
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