Kieran Culkin has been getting a lot of much-deserved praise for his work inA Real Pain, but the on-screen persona that’s made him so iconic originated 23 years ago inIgby Goes Down. Culkin has been sweeping the Best Supporting Actor categories this awards season withhis co-starring role alongside Jesse Eisenberg inA Real Pain, and he’s certainly earned that acclaim. Culkin is hilarious inA Real Pain, but that titular 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 alongsidehis brother Macaulayin the Christmas classicHome Alone, and throughout the ‘90s, he played supporting roles inFather of the Bride,She’s All That, andThe Cider House Rules. But he didn’t get his breakout and prove himself as a lead until he played the title role in the 2002 dark comedyIgby Goes Down.

Kieran Culkin looking sad in 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 Downis one ofthe most underrated movies of the 2000s.Culkin plays Jason “Igby” Slocumb, Jr., a misanthropic 17-year-old boywho 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 — andmaintains a healthy cynicism through all of it.

Igby Goes Downfeatures a star-studded supporting cast including Claire Danes, Jeff Goldblum, Bill Pullman, and Susan Sarandon.

Igby Goes Down (2002) - Poster

Igby Goes Downhas 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 inIgby Goes Down, he might’ve never landed his signature roles inSuccessionandA Real Pain.

Igby Was The Prototype For Roman Roy & Benji Kaplan

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

The seeds ofCulkin’sSuccessioncharacter Roman Royand hisA Real Paincharacter 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 inIgby Goes Down.