In 2025, Kieran Culkin won the Oscar for Best Supporting Actor, beating strong contenders like Yura Borisov. However, his career is much more than just A Real Pain. If you want to see what this talented actor is truly capable of, here are five of his best films.
A Real Pain (2024) – IMDb 8.1
The film that earned Culkin his Oscar. The story follows two cousins who travel to Poland after their grandmother’s death. What starts as a lighthearted family trip soon turns into an emotional journey uncovering old wounds and long-buried family secrets. A mix of drama and dry humor makes this a must-watch.
Succession (2018–2023) – IMDb 8.9
Although it’s a TV series, it’s impossible to overlook. Culkin’s portrayal of Roman Roy, the sharp-tongued, rebellious son of a media mogul, earned him multiple Emmy and Golden Globe nominations. This role cemented his ability to balance comedy and drama flawlessly.
Scott Pilgrim vs. the World (2010) – IMDb 7.5
A visually stunning and stylish adaptation of the comic series, where Culkin played Wallace Wells, the sarcastic and scene-stealing best friend of the protagonist. His sharp wit and comedic timing made him a standout in an already dynamic and visually inventive film.
Igby Goes Down (2002) – IMDb 7.0
One of Culkin’s most defining performances, playing a rebellious teenager from a wealthy family. This role was a precursor to his work in Succession, proving his immense dramatic potential. His performance earned him a Golden Globe nomination.
The Cider House Rules (1999) – IMDb 7.4
A film that received multiple Oscar nominations. Culkin had a small but memorable role as an orphan boy. Though not a central character, this film was a crucial stepping stone in his early career.
From dark comedies to intense dramas, Kieran Culkin has proven himself to be a force to be reckoned with in Hollywood. Whether you’ve been following his career for years or just discovered him through A Real Pain, these films are well worth watching.
