‘Succession’ bros Kieran Culkin, Jeremy Strong will duke it out at Oscars in Best Supporting Actor for ‘A Real Pain,’ ‘The Apprentice’

Kieran Culkin and Jeremy Strong often competed against each other on the Emmy trail for their roles as brothers on “Succession.” Culkin notably beat the “eldest boy” for the final season of HBO’s family drama in 2023, and now a rematch of sorts is on the horizon at the upcoming 2025 Oscars. Both men now contend in the Best Supporting Actor Oscar race, with Culkin at #1 in Gold Derby’s odds for “A Real Pain” and Strong at #8 for “The Apprentice.”

Culkin, who played the wise-cracking youngest son Roman Roy on “Succession,” now takes on the role of Benji Kaplan in Searchlight Pictures’ “A Real Pain.” Benji is the cousin of David Kaplan, played by Jesse Eisenberg (who also wrote and directed the dramedy movie). Together, the cousins embark on a journey through Poland as they remember the life of their late grandmother.

Strong’s “Succession” character of Kendall Roy, who constantly battled internal demons on the show, portrays real-life controversial lawyer Roy Cohn in Briarcliff Entertainment’s “The Apprentice.” As the title suggests, this film focuses on the relationship between Cohn and a young Donald Trump (Sebastian Stan), who will one day become the President of the United States.

“A Real Pain” has an 83 score at Metacritic, a website that aggregates reviews, while “The Apprentice” comes in with a 60 score. Owen Gleiberman (Variety) raves that Culkin in “A Real Pain” delivers a “sensational piece of acting as a compulsive wiseacre addicted to the ways of one-upmanship.” And Maureen Lee Lenker (Entertainment Weekly) writes of Strong in “The Apprentice,” “[The actor] is able to reach beyond the moral rot and corruption of a person to find whatever fragile piece of a soul his characters may possess.”

In our Best Supporting Actor Oscar rankings, Culkin and Strong’s closest rivals look to be Clarence Maclin (“Sing Sing”), Guy Pearce (“The Brutalist”), Denzel Washington (“Gladiator II”), Stanley Tucci (“Conclave”), Samuel L. Jackson (“The Piano Lesson”) and Edward Norton (“A Complete Unknown”). Agree or disagree with these Oscar predictions? Be sure to make your own right now.

Out of Gold Derby’s 26 Expert journalists from major media outlets, 22 predict Culkin will receive a bid, while five say Strong will be nominated. Note that it would be the first career Oscar bids for both of the Emmy-winning actors.

As for our 12 Editors, all 12 think Culkin will get in for Best Supporting Actor at the Academy Awards, while five staffers are also backing a nomination for Strong.

And what do the savvy Top 24 Users think will happen in this category for the “Succession” bros? Currently, 21 of them rank Culkin in their predictions, while four forecast a nom for Strong.

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