One of the Culkin clan of child actors, Kieran Culkin emerged from older brother Macauley Culkin's considerable shadow in the late 1990s. Born and raised in New York, Culkin made his movie debut playing his sibling's cousin in the blockbuster family comedy Home Alone (1990). Along with returning for the sequel Home Alone 2: Lost in New York (1992), Culkin bolstered his presence as a cute foil playing Steve Martin's young son in Father of the Bride (1991) and Father of the Bride Part II (1995). Despite his parents' well-publicized custody battle over their acting brood in the mid-1990s, Culkin continued to work steadily, finally graduating to starring status in The Mighty (1998). As a physically challenged boy who forms a deep bond with an illiterate classmate, Culkin displayed his dramatic abilities as well as comedic, proving that he could be more than just an adorable face. Culkin followed up his lead turn with prominent supporting roles as another little brother in the teen romantic comedy She's All That (1999), Meryl Streep's teenage son in Music of the Heart (1999), and one of the orphans in The Cider House Rules (1999).
After playing at the Sundance Film Festival, The Dangerous Lives of Altar Boys earned strong reviews for Culkin's performance as one of the imaginative, restless Catholic schoolboys grappling with adolescence and dour nun teacher Jodie Foster in the 1970s. A rare teen film with a brain, Altar Boys became an art house success. Delving into the rarified world of the genteel poor, and enhancing Culkin's status as an "alternative" teen lead, Igby Goes Down starred Culkin as the titular alienated son who must deal with harridan mother Susan Sarandon and superficial brother/romantic rival Ryan Phillippe while pondering whether he'll suffer the same fate as his schizophrenic father Bill Pullman.