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In 1991, Culkin starred in an animated Saturday morning cartoon television series, Wish Kid, hosted Saturday Night Live and starred in Michael Jackson's "Black or White" music video. Sennett in the film, My Girl (1991), for which he was nominated for Best On-Screen Duo and won Best Kiss at the MTV Movie Awards, with Anna Chlumsky.He reprised his role of Kevin Mc Callister in the sequel, Home Alone 2: Lost in New York (1992), for which he was nominated for a Kids' Choice Award.
His role as Karen Walker's deceptively immature divorce lawyer won him favorable reviews.
He stopped acting in 1994, making his return in 2003 with a role on the television show Will and Grace and in the film Party Monster (2003).
He wrote an autobiographical book, Junior, which was published in 2006.
In 2013, Culkin co-founded the New York-based, pizza-themed comedy rock band the Pizza Underground, of which he was the vocalist.
They toured in 2014, beginning in Brooklyn on January 24, 2014.