Critics’ Choice Awards 2025: Will Kieran Culkin Win Best Supporting Actor for A Real Pain?

Kieran Culkin has emerged as a top contender this awards season for his performance in the drama A Real Pain. At the recent Golden Globes, Culkin won Best Supporting Actor for playing Benji, a free-spirited character who goes on an emotional journey to Poland with his more straight-laced cousin.

Culkin has already picked up several critics awards, including honors from the New York Film Critics Circle, Screen Actors Guild Awards, and the Los Angeles Film Critics Association. Now he’s nominated for Best Supporting Actor at the upcoming Critics’ Choice Awards on January 12. Can he continue his winning streak?

Culkin’s Acclaimed Performance as Benji

In A Real Pain, written and directed by Jesse Eisenberg, Culkin stars as Benji, who convinces his cousin David (played by Eisenberg) to go on a heritage tour in Poland to honor their late grandmother, a Holocaust survivor. Benji is portrayed as a provocative yet charming stoner type who clashes with his more conservative relative.

Critics have praised Culkin for bringing humor, warmth and complexity to the role. His loose, naturalistic acting style has drawn comparisons to past greats like Jeff Bridges. Culkin makes Benji both infuriating and lovable, showcasing his dramatic range.

Could Culkin Win the Oscar Next?

On the heels of his Golden Globes victory, Culkin’s Oscar prospects are looking up. A Real Pain itself is a strong awards contender, with nominations for Best Original Screenplay and Best Picture (Comedy or Musical) at the Globes.

Culkin is no stranger to accolades, having won an Emmy and Golden Globe for Succession. But this could be his big shot at the Academy Award for Best Supporting Actor. At 42, Culkin is enjoying a career peak after years of strong performances in independent films and TV.

Will Kieran Culkin Win Best Supporting Actor for A Real Pain? 22bet21.com gives odds of 1.143/1 or 88% that he will!

If Culkin wins the Oscar, it would cap off an astonishing awards season run. From his hilarious banter with Mario Lopez at the Golden Globes to his anticipated Critics’ Choice speech, the actor has cemented his status as a Hollywood darling. A supporting actor Oscar win would put him in rare company amongst the Culkin family.

Will Critics’ Choice Win Solidify Oscar Bid?

The Critics’ Choice Awards are seen as a key Oscar precursor. A win for Culkin there would give him significant momentum headed into the Oscar nominations on January 24.

The Critics’ Choice supporting actor category is highly competitive this year. Culkin is up against co-star Jeremy Strong for his role in The Apprentice, as well as experienced actors like Edward Norton (A Complete Unknown) and Denzel Washington (Gladiator II).

But Culkin’s recent streak of awards indicates he is the one to beat. After his hilarious Golden Globes speech, all eyes will be on the actor when the Critics’ Choice Awards air on January 15. A win would likely solidify his place as the Supporting Actor frontrunner.