Macaulay Culkin stole hearts across the world when he starred as the mischievous yet adorable Kevin McCallister in Home Alone. Ever since, he has had quite the Hollywood story. From a young age, the former child star has been surrounded by people in the entertainment industry. His father is Kit Culkin, a Broadway actor, and his aunt is Bonnie Bedelia, an Emmy-winning actress who has starred in shows including Love of Life and Parenthood and movies such as Die Hard and Needful Things. Two of his younger brothers, Kieran Culkin and Rory Culkin, also went on to find fame as actors. Macaulay began acting at the age of 4. After landing small roles in the 1985 made-for-TV movie The Midnight Hour and a 1988 episode of The Equalizer, he made his big-screen debut as Cy Blue Black in the 1998 film Rocket Gibraltar. The following year, he starred opposite John Candy in Uncle Buck. The New York City native got his big break in 1990 when he starred in Home Alone. The Christmas classic reunited him with Candy (who played polka musician Gus Polinski) and John Hughes, who directed both Uncle Buck and Home Alone. For his role as Kevin, Macaulay won an American Comedy Award and a Young Artist Award and received a Golden Globe nomination. Macaulay’s big role made him an overnight sensation, landing him a hosting gig in a 1991 episode of Saturday Night Live and a part in Michael Jackson’s “Black or White” music video. He reprised his role as Kevin in 1992’s Home Alone 2: Lost in New York, which also became a huge success. Home Alone aside, Macaulay continued acting throughout the early ‘90s in movies including 1991’s My Girl, 1993’s The Good Son and 1994’s The Pagemaster. He took a break later in 1994 to return to school. “I just wanted a little bit of a break,” he told Time magazine in a 2001 profile. “I wanted a summer vacation for the first time in, you know, forever.” The actor resumed his career in 2000 in the play Madame Melville on London’s West End. He later made a guest appearance on Will & Grace before returning to film with roles in 2003’s Party Monster, 2004’s Saved! and 2007’s Sex and Breakfast. He also published a semi-autobiographical book, Junior, in 2006. Macaulay shifted his focus to music in 2013 after going viral over a YouTube video of him eating pizza. He turned life into art when he formed the comedy rock band The Pizza Underground. The group released several music videos and toured North America and Europe before splitting in 2018. The “Bunny Ears Podcast” host has also made headlines over the years for his once-erratic behavior and high-profile relationships. He was briefly married to actress Rachel Miner and had a long-term relationship with Mila Kunis before he started seeing his Changeland costar Brenda Song in 2017. The twosome, who share son Dakota, got engaged in 2022. Scroll down to see photos of Macaulay through the years!