A former child star and Michael Jackson protégé, Culkin has been trying to shake his indelible Home Alone image with roles in edgy indie movies like Party Monster and Saved!

Born in Manhattan, the adorably precocious Culkin landed his first major role in 1989's Uncle Buck with John Candy. Just two short years later, he gained international recognition in the blockbuster hit Home Alone. One of the highest grossing comedies of all time, Macaulay became the 90s most in-demand child star, hosting SNL at the tender age of 11 (only to be beaten by Drew Barrymore, who hosted when she was 7), starring in beloved family films like My Girl and Richie Rich, and reprising his role as Kevin McCallister in Home Alone 2: Lost in New York. After taking a much-needed break from the spotlight (for his sake as much as our own), Culkin came back ready to prove that he wasn't a kid anymore as the druggie "King of the Club Kids" in Party Monster and as a wheelchair-bound atheist in Saved! He also took on various small, "experimental" roles, like The Wrong Ferrari, which was shot entirely on an iPhone. His steadiest recent work came doing voice-over work for Seth Green's Robot Chicken from 2005-2010.

Although his professional life has been sleepy, Culkin's has some juicy skeletons in his closet. He's hinted at conflict in his family life and is estranged from his father (which can be inferred from his weird, semi-autobiographical novel Junior). Culkin got misguidedly hitched when he was 18 to actress Rachel Miner, and in 2004 was arrested for drug possession. Around the time of Home Alone's release, Culkin became chummy with the late Michael Jackson in his "Black or White" music video and attended a few notorious slumber parties. During the infamous dove-releasing Michael Jackson trial, Culkin testified that he had slept in Jackson's bedroom several times but attested that Jackson never inappropriately touched him and that the allegations were "absolutely ridiculous." During Culkin's attempt at a more mature career, he began dating actress Mila Kunis, but the pair split in 2011 after dating for 9 years. [Image via Getty]