It was a huge night at the 2025 Oscars, not least for Best Supporting actor winner, Kieran Culkin. The actor punctuated his nearly 40-years long career with his first nomination and win at the 97th Oscars, thanks to his role in Jesse Eisenberg's A Real Pain.

The film stars Culkin and Eisenberg as cousins, who embark together on a group Jewish heritage tour through Poland in the wake of their grandmother's death. The film quickly gained attention for its delicate balance of humour and trauma, but it was Culkin's performance as Benji that really stole the show. While you've no doubt seen and loved Culkin's portrayal, A Real Pain might have left you hungry for more of his witty (often improvised) quips. But want no more, there's plenty more hilariously sharp observations where they came from. Below, we're rounding up Culkin's best work to date, from Father Of The Bride to Succession.

1. Father Of The Bride (1999)

Okay, it was only a small role, but it feels right to begin with a classic. In 1991 (when he was just 9), Culkin played Matty Banks, the young son of Steve Martin and Diane Keaton's characters. The film follows the Banks family as they prepare for their elder daughter, Annie's, wedding — and all the comical, endearing mishaps it brings along with it.

2. Igby Goes Down (2002)

In 2002, Culkin came into his own as the titular character in Igby Goes Down. The film charts Igby, a cynical teenager who attempts to rid himself of his overbearing family. If the plot wasn't enough to get you interested, the supporting cast might be. Alongside Culkin, Igby Goes Down stars Jeff Goldblum, Clare Danes, Susan Sarandon, Amanda Peet, and Ryan Phillipe. Notably, Culkin and Sarandon both earned Golden Globes nominations for their performances.

3. The Dangerous Lives Of Alter Boys (2002)

In this comedy-drama, Culkin plays Tim Sullivan, one member of a group of Catholic school friends in the Southern United States in the 1970s. When the mischievous group are caught working on their comic book, The Atomic Trinity, they set out to devise the ultimate prank that will propel them to legendary status at school.

4. Scott Pilgrim vs. The World (2010)

This 2010 comic book adaptation has a legion of cult followers, even 15 years later. Funny and often a little bizarre, Culkin's character, Wallace Wells, is the searingly honest voice of reason throughout.

5. Infinity Baby (2017)

For a thought-provoking watch that's unlike anything else out there, look no further. The premise of film is simple: a compnay, Infinity Baby, provides ageless babies to parents who want children that will never grow up. Culkin plays Ben, the protagonist and a young employee at Infinity Baby, whose own commitment issues are a metaphor for the children he is farming.

6. Succession (2018 - 2023)

It's not a film, but we couldn't write about Culkin's best performances and leave Roman Roy off the list. Arguably the character he'll be remembered for best, the hilariously immature son of media mogul Logan Roy, and a role that earned Culkin his first Emmy award.

Feature image via IMDb.