Kieran Culkin has been getting a lot of much-deserved praise for his work in A Real Pain, but the on-screen persona that’s made him so iconic originated 23 years ago in Igby Goes Down. Culkin has been sweeping the Best Supporting Actor categories this awards season with his co-starring role alongside Jesse Eisenberg in A Real Pain, and he’s certainly earned that acclaim. Culkin is hilarious in A Real Pain, but that тιтular emotional anguish is always simmering just under the surface.

Coming from a family of performers, Culkin has been acting since the age of two. He made his film debut in 1990 when he played Fuller McCallister alongside his brother Macaulay in the Christmas classic Home Alone, and throughout the ‘90s, he played supporting roles in Father of the Bride, She’s All That, and The Cider House Rules. But he didn’t get his breakout and prove himself as a lead until he played the тιтle role in the 2002 dark comedy Igby Goes Down.

Long Before A Real Pain & Succession, Kieran Culkin Starred In Igby Goes Down

Igby Goes Down Is A Delightfully Dark Comedy

Written and directed by Burr Steers, Igby Goes Down is one of the most underrated movies of the 2000s. Culkin plays Jason “Igby” Slocumb, Jr., a misanthropic 17-year-old boy who desperately wants to break free from the trappings of his old-money family. Igby is surrounded by chaos from his schizophrenic father, his cruel, overbearing mother, and his neo-fascist older brother. He gets savagely beaten at military school, he enables a heroin addict while squatting in his godfather’s art studio, and he gets his heart broken by his unfaithful girlfriend — and maintains a healthy cynicism through all of it.

Igby Goes Down has a wonderfully twisted sense of humor, and it’s more of a character study than a straightforward plot, meaning the spotlight is squarely on Culkin’s performance. He effortlessly anchors the movie with a character who isn’t totally likable, but is utterly compelling (and oddly charming, despite his obvious flaws). If Culkin hadn’t proven his ability to bring real dramatic depth to a darkly comedic character in Igby Goes Down, he might’ve never landed his signature roles in Succession and A Real Pain.

Igby Was The Prototype For Roman Roy & Benji Kaplan

Culkin Honed His Snarky Yet Vulnerable On-Screen Persona As Igby

The seeds of Culkin’s Succession character Roman Roy and his A Real Pain character Benji Kaplan can be seen in his performance as Igby. Like Roman and Benji, Igby is snarky and sardonic on the surface, with a wry one-liner up his sleeve at every turn, but he’s deeply vulnerable at his core. This is an on-screen persona that Culkin has perfected throughout his career, and it can be traced back to his performance in Igby Goes Down.