In the first announcement at the 97th Academy Awards, Kieran Culkin won the Best Supporting Actor Oscar for his performance in A Real Pain. This marks Culkin's first Oscar, and it follows up his wins in the category at the Golden Globes, Critics' Choice Awards, the BAFTAs, and Film Independent Spirit Awards. Robert Downey Jr, who won in the same category last year for his performance in Oppenheimer, announced the award. His fellow nominees included Yura Borisov (Anora), Edward Norton (A Complete Unknown), Guy Pearce (The Brutalist), and Jeremy Strong (The Apprentice).

In the Jesse Eisenberg directorial, Culkin stars as one of two American cousins who visits Poland to honour their late grandmother's wishes. In our review of the film, we described the actor as "immensely likeable as well as sadly devastating" in the role of Benji Kaplan.

In his acceptance speech, Culkin commended his fellow nominees, most notably his Succession co-star Jeremy Strong. Last year, the actor won a best actor Emmy in a drama series for his performance in Succession, beating his co-stars Brian Cox and Strong, among others. Culkin also thanked his wife Jazz Charton and shared a humorous anecdote about his wife promising that they could have another child if he were to win an Oscar.