Macaulay Culkin was one of Hollywood's biggest child stars of the 90s after becoming a household name following his starring role in Home Alone.
But like many child stars, the actor underwent a series of turbulent years that couldn’t be more different from his life onscreen.
Following his meteoric rise to fame, he went through a painful emancipation from his parents – where he accused his father of leeching off his success.
Macaulay took a break from acting, got married at just 18, lost two of his family members at a young age, and allegedly got hooked on drugs.
However lately, he’s appeared to have left his troubled past behind, recently welcoming a baby girl with his girlfriend Brenda Song earlier this year.
On his 40th birthday last year, he tweeted: "Hey guys, wanna feel old? I'm 40. You're welcome."
The tweet went on to become the ninth most-liked tweet of all time.
Early beginnings
Macaulay Culkin was born on August 26, 1980, in New York City, to Christopher Cornelius "Kit" Culkin and Patricia Brentrup.
The family were reportedly very poor when Macaulay was little.
According to E! Online, Billy Hopkins, a New York casting director who gave a six-year-old Macaulay his first part, said: "Macaulay would crawl under the bleachers at the theatre to look for change that had fallen out of people's pockets. They were like the Beverly Hillbillies.”
However, that all changed when Macaulay became a child star, landing major roles in Rocket Gibraltar (1988) and Uncle Buck (1989).
But he shot to international stardom when he played Kevin McCallister in the Christmas movie Home Alone in 1990 and he reprised the role for Home Alone 2: Lost in New York two years later.
After the success of Home Alone, he went on to star in My Girl (1991), The Good Son (1993), The Pagemaster (1994) and Richie Rich (1994).
Macaulay went on to become the second-youngest celebrity to host Saturday Night Live, aged 11.
Family emancipation
Kit and Patricia announced they were separating after 20 years in 1994, sparking a bitter custody war.
While Macaulay reportedly sided with his mum at the time, he later famously "divorced" both his parents when they began fighting over his fortune.
He sued his parents for £13million when he was just 15 years old and had them removed as his legal guardians, meaning they had no control over his career or money.
"I even wanted to take a break for a while and eventually I was like 'I'm done guys, hope you all made your money because there is no more coming from me'," he told Marc Maron's WTF podcast in 2018.
"Everything he tried to do in life, I excelled at before I was 10 years old," he went on.
Family tragedy
In 2000, Macaulay sadly lost his half-sister, Jennifer Adamson, after she died from a drug overdose.
Then, just eight years later, his sister Dakota Culkin was tragically killed in a car accident when she was just 29.
She “was struck by a car when she stepped off the curb and in front of a moving vehicle", according to E! News.
Relationship with Michael Jackson
Macaulay was very good friends with the late Michael Jackson from the early 90s, right up until his death in 2009.
In 2019 Macaulay revealed that he and Michael became friends because they both knew what it was like to be a "child who was famous”.
The actor famously spoke up in defence of her dad Michael when he faced child molestation charges in 2003 – something which the late singer was acquitted of.
He was even chosen to be the godfather of Michael’s daughter Paris Jackson.
The pair are incredible close and have even gotten matching tattoos of red spoons to symbolise how they’ve overcome an incredibly amount of trials in their life.
Romantic life
Macaulay went on to marry actress Rachel Miner in 1998, aged just 18 after meeting in high school.
But sadly the young love didn’t last, and the couple separated in 2000, divorcing in 2002.
He went on to date actress Mila Kunis for almost a decade, before splitting in 2010.
She told Women's Health of their relationship in 2009: "You find a steady rock in your life and that’s all you need.”
When they eventually split, Mila told the Armchair Expert podcast: "[It was] a horrible, horrible breakup. I f***ed up."
Arrest
Macaulay has been plagued by rumours of heroin addiction in the past, after pictures of him looking ragged appeared online.
He has denied this, telling The Guardian: "I was not pounding six grand of heroin a month.”
However, he did plead guilty to misdemeanour drug charges in 2005, one for possessing medication without a prescription and the other for marijuana.
He was given a one-year deferred sentence on each charge, and was ordered to pay $540 in fees.
Later life
The star managed to turn his life around and these days looks a lot happier and healthier.
In a recent interview with Esquire, he said: "I played with some fire, I guess is the best way to put it. At the same time, I’ve never been to rehab or anything like that.”
He added: "Besides the occasional muscle relaxer, no, I don’t do drugs recreationally. I still kinda drink like a fish. I drink and I smoke. But I don’t touch the things."
One of his more bizarre projects was when he set up a Velvet Underground tribute band, called the Pizza Underground and replaced all the lyrics with pizza subjects.
He also announced in December 2018, that he would legally change his name to "Macaulay Macaulay Culkin Culkin" after holding a vote through his website to choose a new middle name.
Recently, Macaulay founded a lifestyle brand named "bunny ears”.
The brand’s site states: ”We want to explore the modern lifestyle choices that people make in great depth because we know that healthy relationships and mental wellness are the keys to happiness.”
Fatherhood
Since July 2017, Macaulay has been in a relationship with actress Brenda Song, after meeting on the set of their movie Changeland.
The couple now live together and have three cats – Apples, Dude, and Santa – and a fish named Cinnamon.
On April 5, 2021, the Disney Channel alum gave birth in Los Angeles to their first child together, son Dakota, weighing 6 pounds, 14 ounces.
The couple told Esquire that they're "overjoyed" and named their baby boy after Macaulay's late sister.
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