Macaulay Culkin Through the Years: His Transformation in Photos 

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. [sendtonews type="float" key="BoGXtMgdkp-2840054-14453"] 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!

Macaulay starred alongside Burt Lancaster, Patricia Clarkson and Frances Conroy in his first movie, 1998’s Rocket Gibraltar.

He played the middle child of Candy’s character in Uncle Buck in 1989.

Macaulay most famously starred as an 8-year-old boy whose family accidentally leaves him behind when they travel to Paris for Christmas in 1990’s Home Alone.

The child star hosted SNL with musical guest Tin Machine in 1991. During the cold open, he dreamed of hosting the NBC variety show by himself after series creator Lorne Michaels and the cast were mean to him, a nod to Home Alone.

Macaulay was one of four celebrities featured in Jackson’s “Black or White” video in 1991, joining Tyra Banks, Tess Harper and George Wendt. He and the late King of Pop were close friends for years, and Macaulay famously testified in support of Jackson during the “Thriller” singer’s 2005 molestation trial.

In his second and final Home Alone movie, Macaulay took a solo trip to NYC while his family vacationed in Chicago. He did not return as Kevin for 1997’s Home Alone 3 or 2002’s Home Alone 4.

He married Miner in June 1998 when they were both 18. The pair separated in August 2000 and finalized their divorce two years later.

After a six-year hiatus, Macaulay returned to work in a 2000 production of Madame Melville.

The web host started dating Kunis in May 2002. They amicably split in late 2010. The That ‘70s Show alum later took the blame for their separation, saying on Dax Shepard’s “Armchair Expert” podcast in 2018 that she did something “f--ked up” but “everybody kind of forgave everybody for what went down.”

Macaulay was arrested in Oklahoma in 2004 for drug possession. After pleading guilty, he received three one-year suspended prison sentences and was ordered to pay $540 in court fees.

The musician performed with The Pizza Underground from 2013 to 2018. Concertgoers infamously booed and threw beer at the band during a headline-making 2014 show in England.

Macaulay met Song in 2017 on the set of their movie, Changeland, which premiered two years later. They have been going strong ever since, and he said in a 2020 interview with Esquire that they “practice a lot” so they can start a family.

The movie star hilariously recreated scenes from Home Alone in a 2018 Google Assistant commercial.

Macaulay joined the cast of American Horror Story season 10 in 2020.

Macaulay welcomed his first child, son Dakota, with Song in April.

Us confirmed in January that the “Bunny Ears” podcast host was engaged to the former Disney Channel star.

Us broke the news that the Good Son star and the Suite Life on Deck alum had secretly welcomed their second child, son Carson, in December 2022. 

The couple dressed to impress at the Academy Museum of Motion Pictures 4th Annual Gala in October 2024. 

Culkin revealed the secret to his lasting relationship with Song a few months later. 

"Brenda and I are very good at communicating with each other," he told E! News December 2024. "We have no secrets. We're constantly on the line — we talk, we talk."

Culkin and Song wore coordinating cream outfits to the 2025 Vanity Fair Oscar Party in March 2025. She stunned in a strapless gown with ruching along the bodice and silver jewelry, while he was all smiles in a tuxedo.