Marketed as a Culkin showcase (though he was actually a supporting player), "My Girl" (1991) aroused some controversy over his character's death at the end of the film, from a bee sting; psychologists wondered whether the youth of America could stand the trauma of "losing" such a beloved figure, and critics felt obliged to warn parents by giving away the ending in their reviews. Culkin followed up with a cameo in another Hughes production "Only the Lonely" (1991) before getting down to the serious business of making lightning strike twice with the same concept. For his efforts, Culkin reportedly received $5 million for the immensely successful "Home Alone 2: Lost in New York" (1992).
At the ripe old age of 12, Culkin made a bold but smart career move by accepting the lead role of the antagonist in "The Good Son" (1993). Here he was the personification of pure evil behind his sunny blond facade. This change-of-pace characterization reportedly nabbed the little franchise anywhere from $5-8 million--in any event, a nice buffer for the potentially career ravaging travails of puberty. The film received mixed reviews and enjoyed modest box-office success. Mac was next paired with Ted Danson for the poorly received comedy "Getting Even With Dad" (1994) and had a moderate success with the comic book-inspired "Richie Rich" (also 1994).
Culkin spent the next few years embroiled in a bitter dispute with his father over control of his finances. He was officially "divorced" from his father and manager over his $30 million fortune. This situation led Culkin decide he would take a break from acting and soon he all but disappeared from the public eye; the most notable development in his life was his marriage to actress Rachel Miner in 1998 when both were 18. After spliting from his wife in 2000 he resumed his acting career, appearing in a West End production of Madame Melville in London where he received rave reviews. He repeated his role in the New York production in 2001. After an amusing TV guest spot playing a young, innocent-looking but shark-like attorney on "Will & Grace" in 2003, Culkin at last returned to feature films in the inspired-by-true events tale "Party Monster" (2003), where he portrayed a fey, flamboyant young party promoter in the 1980s who finds himself charged with murder. Despite his lengthy absence, the actor received strong reviews for his appropriately high camp performance. The actor also turned in a sly, deft comedic turn as the wheelchair bound brother of Christ-obsessed Mandy Moore in the spoof of religious high schools "Saved!" (2004), and he displayed a surprising degree of sex appeal in his scenes with "bad girl" Eva Amurri. Less promising for his comeback was the fact that in 2005 he had to both face drug charges in court (he pleaded guilty to misdemeanor charges of possession of medication without a prescription and marijuana, and was given a deferred sentence and fined $540) and he was required to testify for the defense in the child molestation trial of pop star Michael Jackson, who had befriended Culkin in his youth; the young actor told a jury that he had never been molested by Jackson after other witnesses testified that they had seen inapporpriate sexual behavior between the two during the early 1990s.