Macaulay Culkin ushered in the new era of the troubled child star, becoming one of the most infamous child actors to grow up in the limelight only to have fame, wealth, and success become more of a burden than a blessing. Read on for some highlights of the Home Alone star’s highest and lowest life moments thus far.
Culkin’s parents, Kit and Patricia, came from incredibly modest beginnings prior to Macaulay’s success. As one of seven children, he would scramble for change to augment his church-working father’s and telephone operator mother’s salaries.
Father Kit would eventually take on the managerial role for his son, gaining quite a reputation for hardline negotiations and bigger paydays for his son. Supposedly, Kit was itching more for power than for money, perhaps in part due to his own ill-fated run at acting.
Home Alone was a family affair in more ways than one: Culkin’s real-life brother, Kieran, played his younger cousin, Fuller. Kieran as well as their brother Rory followed in Macaulay’s footsteps, also having been bitten by the acting bug.
Joe Pesci, the more disciplined of the two “wet bandits,” scared Culkin during the filming of Home Alone, likely because Pesci was still in the zone of his Goodfellas mob character.
Home Alone grossed nearly a half-billion dollars worldwide, while the sequel netted $359 million. Culkin’s star was so bright that he was offered $8 million for 1994’s Richie Rich, making him one of the highest paid child actors in history.
Despite his mega earnings, Culkin’s parents hid his wealth and the headlines that exposed as such so that he wouldn’t grow up spoiled and entitled.
Culkin received his first kiss — both onscreen and in real life — at the age of 11 in a scene of My Girl, costarring Anna Clumsky. The liplock was endearing enough to win the MTV Movie Award for Best Kiss.
Adding to the Culkin family saga, he tragically lost two of his sisters, both at the young age of 29. A half-sister died from a toxic overdose, while older sister Dakota was fatally struck by a car.
Culkin practiced his verbal skills and line delivery by prepping with tongue twisters. He loved them so much that he even created some of his own with which to practice.
In thanks to the heightened scrutiny and media attention he’s received all his life, Culkin early on came to realize that his eyes are of two unequal sizes, proving that imperfections won’t necessarily prevent you from box office gold.
Culkin was a favorite guest at Michael Jackson’s Neverland Ranch at the height of the child star’s fame in the 1990s. Once allegations of abuse plagued Jackson in the press, Culkin vehemently denied that any wrongdoing happened between the stars, who both suffered from getting too famous too young.
In 1998, Culkin’s mother accidentally caused a lethal fire in her apartment, causing the death of four people and the injuries of another 22. Lawsuits followed, even against Culkin himself, who wasn’t even in the vicinity at the time of the fatal event.
Culkin ended up meeting his first wife, actress Rachel Miner, in high school, though he wasn’t so friendly to her when she first transferred to his school. They eventually had an on-again, off-again relationship, finally settling down on the fourth go around.
Rumors spread that following his separation from Miner, he began to date model Agatha Relota, and then porn star Irene Lopez. Culkin denies both flings, though photographs and sightings may indicate otherwise.
Fresh off his divorce, Culkin began dating That ’70s Show star Mila Kunis. The two remained an item for a lengthy eight years before splitting in 2010. She originally claimed she was against marriage until marriage equality became legal in the US, and she’d eventually marry costar Ashton Kutcher.
Following his breakup with Kunis, Culkin was seen in Paris holding hands and dancing in the streets with brunette beauty Jordan Lane Price, a star of the online soap series All My Children.
One dirty habit he’s picked up is an unhealthy addiction to tobacco and nicotine, which at one point totaled a whopping 60 cigarettes a day. This unhealthy lifestyle may have been spurred by The Libertines frontman (and Kate Moss’s ex) Pete Doherty, with whom he once lived.
Culkin’s also had to put rumors of substance abuse to rest. Onlookers in London have witnessed him looking pale and rather homeless, though perhaps it’s just his nonchalant style and unfazed attitude.
Though Culkin starred in Home Alone and Home Alone 2, he opted to sit out for the third installment of the trilogy. However, a 2015 web series called :DRYVRSfollows Kevin McCallister all grown up, still shaken by his childhood abandonment at Christmas.