Tragic Details About Macaulay Culkin

Imagine what it would be like to be a middle-aged actor who is best remembered for a role you played in a now-iconic movie at the age of 9. And then imagine that movie reappears each holiday season, playing on a seemingly endless loop on TV screens, further cementing the public's association with your childhood self. 

Welcome to the world of Macaulay Culkin, whose role as youngster Kevin McCallister in the 1990 Christmastime classic "Home Alone" is not only seared in our collective pop-culture memories but continues to eclipse pretty much everything else that he's done since. Culkin, in fact, did manage to establish himself as an adult actor following the massive success he achieved as a kid — no mean feat, given that the typical trajectory following child stardom has often involved multiple stints in rehab, financial insolvency, and the occasional prison sentence.

That may not have quite been Culkin's experience after becoming arguably the biggest child star of the 1990s, but that's not to say he hasn't experienced some serious travails in his life. He's enjoyed triumphs, both professionally and personally, but there's also been no shortage of adversity accompanying him on that journey. "He has gone through so much tragedy," Culkin's partner, actor Brenda Song, told Esquire. "He's had so many ups, so many downs; he's seen the ugly side of this industry." To find out more, read on for a look at some tragic details about Macaulay Culkin.

Macaulay Culkin is the third of seven children born to Kit Culkin and common-law wife Patricia Brentrup, and it's hardly an understatement to observe that he was not born with a proverbial silver spoon in his mouth; in fact, financial insecurity was pretty much a constant during his childhood. The elder Culkin was a struggling actor who'd landed a few small roles on Broadway before his career stalled, leading him to bring in money by driving a cab and working as a sacristan for a Catholic church. Brentrup, while raising all those kids, held down an evening job at a telephone answering service. 

Culkin, his six siblings, and their parents lived together in a small railway apartment in New York City, with all seven Culkin kids sharing a single room and sleeping in bunk beds. "It was basically one long hallway separated by doorways with no doors," Culkin recalled in an interview with New York Magazine.

His younger brother, "Succession" star Kieran Culkin, shared his own memories of the family's living situation with Vanity Fair, recalling the tiny apartment was "barely suitable for a couple," let along a family of nine. "They raised seven kids in that apartment — for years!" he said. "They just kept bringing babies home to this little space."

When young Macaulay Culkin began landing acting roles, that success dramatically changed the family's fortunes. While he earned a mere $100,000 for "Home Alone," he raked in substantially more for the sequel, and at his peak was commanding $8 million a picture. Kit Culkin — who became Macaulay's manager — moved the family from that small apartment to a posh brownstone in Manhattan's Upper East Side. The youngster observed that as his own stardom grew, it was in direct proportion to the resentment his father held toward him once he'd become the family's de facto golden goose.

"My father was jealous of me," Culkin explained during a 2018 appearance on Marc Maron's "WTF" podcast, as reported by The Hollywood Reporter. "He was a bad man. He was abusive. Everything he tried to do in life, I excelled at before I was 10 years old."

Culkin's remarks elaborated on earlier comments he'd made during a 2004 interview with "Larry King Live," when he discussed his father's controlling nature. "He played games with you, just to make sure you were still in your place," Culkin said, recalling how — when he was a teenager with a net worth of millions — his father forced him to sleep on a couch, refusing to let him have his own bedroom. "It was more to prove a point, I think," Culkin mused.

Macaulay Culkin was a teenager when his parents split up. The breakup led to a bitter court battle over custody of their minor children, which included him. During the trial, he learned how much money he'd actually earned. "My father would hide newspapers from me so I wouldn't read the stuff about him or find out how much I was making," Culkin told New York Magazine, adding, "They didn't want me running off to my friends saying, 'I just made $8 million!'"

A judge ultimately awarded sole custody of Culkin and his four younger siblings to his mother; a big part of that decision, reported UPI, was that Culkin and his brother, Kieran, testified that they wanted nothing to do with their father. "Macaulay and Kieran insist they will not work with Mr. Culkin," said New York State Supreme Court Justice David Saxe.

"It's always misconstrued, that I 'emancipated' myself from my parents," Culkin told Esquire. "I legally took my parents' names off of my trust fund and found an executor, someone who would look over my finances, just in case anyone wanted to stick their f***ing pinkie in the pie." While his intent was to remove both parents from a guardianship role over his finances to make a messy situation easier, that wasn't how the situation was reported. "But the next thing you know," he recalled, "the story was that I divorced my parents." 

Macaulay Culkin turned 43 in 2023, yet is still immediately recognizable to anyone who saw him in "Home Alone" or any of the other movies he made when he was a kid. Every time he goes out in public, he told Vulture, he can feel people's eyes on him. "And even if I don't get bugged, it's looming, it's there," he said. As a result, he's become something of a night owl. "I'll take walks at two or four in the morning, because there's nobody out on the streets and it's easy for me to go unnoticed," he added.

While spending time in Paris, however, Culkin realized he wasn't being approached by fans as much as he usually was. This led him to believe that perhaps he simply wasn't that well-known in France. "It turned out that no, they recognized me, they just didn't care," he said. "I was like, 'Where have you people been my entire life?'"

That recognition, and the public's unrelenting interest in him, has also led him to be continually stalked by paparazzi. As Culkin told The Guardian in 2016, he finds the whole thing to be more than a little puzzling. "I was thinking about this the other day — I'd crossed the wrong street, picked up a tail, suddenly there's a crush of 20 paparazzi. Then people with cameraphones get involved. I don't think I'm worthy of that."

After spending much of his childhood on movie sets, serving as a cash cow for his parents, teenage Macaulay Culkin had become burned out. He desperately wanted to take some time off. "I just wanted a little bit of a break. I wanted a summer vacation for the first time in, you know, forever," Culkin told Time.

As he explained while appearing on "Larry King Live," the pace at which he was working had taken a toll on him. "I did 14 movies in six years, which is more than two a year, and just kind of pumping them out," he explained. "And I was at this point where I really wanted to take a break ... I always joke, 'Yeah, I retired at 14.'"

After his "retirement," Culkin began reveling in living the life of a typical teenager, including going to high school at the Professional Children's School, which caters to child actors and other kids involved in creative careers. Even though he'd stopped making movies and retreated from Hollywood, his fame remained undiminished, something he realized when he dyed his hair crazy colors. "I did purple and I did pink and I did orange, and they made such a big deal out of it — it was on the cover of People!" he told New York Magazine.

While attending Professional Children's School, Macaulay Culkin met fellow student Rachel Miner when he was just 14. "We hung out in a big group of people, and you start kind of pairing off," Culkin told New York Magazine in 2001, recalling their on-again, off-again relationship during their teen years. "She'd broken up with me three times before, and so the last time we were going out I said, 'Marry me now before you dump me again.'"

She agreed, and in 1998 the two tied the knot when they were both just 17. It didn't take long for the marriage to unravel, and in 2000 they separated. They subsequently got a divorce, which was finalized in 2002. "They were really in love and everyone was against it, especially the parents," one of Culkin's told Fox News of the doomed marriage. "But it was a crazy time, and they just did it." 

Two years after the divorce, he addressed his brief failed marriage while appearing on "Larry King Live." "You never want something like that to happen," he said. "And of course when we got married we thought we'd be together forever."

After his divorce, Macaulay Culkin's next major relationship was with Mila Kunis, star of TV sitcom "That '70s Show." They began dating when they were in their early 20s. Interviewed by Women's Health in 2009, Kunis — who'd been dating Culkin for seven years at that point — said of her beau: "I don't know if I met him at 27 if it would have been a different relationship. We grew up together." At that time, she also confessed it hadn't always been smooth sailing. "We have our ups and downs," Kunis admitted, "but work through them."

In 2011, Page Six reported that they'd broken up. "The split was amicable," Kunis' rep told the outlet, "and they remain close friends."

While neither have really discussed the precise circumstances that had led that long-term relationship to end, Kunis shouldered the blame when she appeared as a guest on Dax Shepard's "Armchair Expert" podcast. Describing their split as "a horrible, horrible breakup." She added: "I f***ed up. I was an a**hole in my 20s and I'll be the first to admit it," she said. Without offering any details about her behavior, she insisted she didn't cheat on Culkin, but did point to some sort of terrible transgression. "It's f***ed up what I did, and it's f***ed up how I did it," she said.

A 2004 road trip turned into an unanticipated brush with the law when Macaulay Culkin were pulled over for speeding while driving in Oklahoma. When police searched the car — in which Culkin was the passenger, not the driver — more than 17 grams of marijuana was discovered, along with several Xanax and clonazepam pills, none of which Culkin had a prescription for. 

Culkin was placed under arrest and charged with possession of both marijuana, and of a controlled substance without a prescription. He was subsequently released on $4,000 bail. As the police report indicated (as documented by The Smoking Gun), it was Culkin's squirrelly behavior during the traffic stop that had heightened the cops' suspicions enough to search the vehicle. "[Culkin] appeared to have a very nervous look on his face, appeared to be very pale and he had red watery bloodshot eyes and a very stressed look about his person," noted the report.

Culkin pled guilty to both charges. He got off with a slap on the wrist, receiving two one-year sentences, both of which were deferred. He was also ordered to cough up a $540 fine.

After Macaulay Culkin's 2004 drug bust, rumors began to arise that he'd succumbed to the kind of substance abuse that has sadly become common among former child stars. In 2012, the National Enquirer reported that Culkin was strung out on heroin, spending $6,000 a month to feed an addiction so severe that he'd be lucky to be alive in six months' time. 

In response, Culkin's rep issued a statement to E! News, declaring that "the report in the National Enquirer that Macaulay Culkin is addicted to heroin and assorted hallucinogenics is not only categorically without merit, but it is also impossibly and ridiculously fictitious."

Years later, Culkin dismissed the tabloid rumors. "I was not pounding six grand of heroin every month or whatever," he told The Guardian in 2016. A few years after that, however, he admitted he that he had flirted with drugs, but at nowhere near the level that the Enquirer had been claiming. "I played with some fire, I guess is the best way to put it," he told Esquire. "At the same time, I've never been to rehab or anything like that. I've never had to clean out that way."

In 2008, Macaulay Culkin's older sister, Dakota, was hit by a car while walking in Los Angeles. Just a year older than the "Home Alone" star, she died shortly after the accident. Speaking with Esquire more than a decade later, Culkin reflected on the tragic loss. "She passed away 11 years ago tomorrow," he said. "Tonight," he added, as in 11 years to the day, "was the last time I talked to her, and she passed away overnight, kinda thing."

Their final conversation was a poignant one. As Culkin recalled, his sister had just watched "Party Monster," his first movie as an adult, and called to congratulate him on his performance. "She said, 'I want you to stay focused and enthused.' I was like, 'Thanks. You too. Go to sleep.' And then she went out to go get some Gatorade and cigarettes, and she got hit by a car."

Her death affected all the Culkin siblings in very profound ways. "That's the worst thing that's ever happened, and there's no sugarcoating that one," Culkin's brother, Kieran Culkin, told The Hollywood Reporter. "Each one of us handled it very differently. I think everyone was just torn up inside." In tribute to his late sister, Culkin and partner Brenda Song named their first child Dakota.

Back in 2013, Macaulay Culkin made a sharp detour from acting into music with the formation of his comedic musical group The Pizza Underground. The concept was quirky bordering on bizarre, with Culkin — showcasing his musical virtuosity on the kazoo — and his bandmates performing parody versions of songs by Lou Reed's iconic proto-punk rock band The Velvet Underground, but with lyrics rejigged to be all about pizza.  

Despite the silliness of the concept, Culkin apparently took The Pizza Underground seriously. That was evident when he announced the band would be embarking on a brief tour of the U.K. To describe that tour as disastrous would be quite an understatement. While the group performed at a venue in Nottingham, the audience — clearly not getting the joke at the center of the group's concept — expressed their displeasure with the sounds emanating from the stage by laying siege to Culkin and his cohorts, pelting them with pints of beer. Culkin tried to calm things down by joking with the audience; according to the Nottingham Post, he told the crowd: "Why are you throwing those? I'd rather drink them!"

That did not result in less beer thrown, however. After performing for all of 15 minutes, Culkin decided he'd had enough, and left the stage. Soon after that debacle, The Pizza Underground canceled the rest of its U.K. dates.

After shutting his father out of his life when he was a teenager, the rift between Macaulay Culkin and his dad, Kit Culkin, not only remained, but apparently intensified over the years. In 2014, TMZ reported that Kit, then 69, suffered an enormous stroke that left him hospitalized, with severe damage to most of his motor functions. TMZ subsequently reported that Kit had been striving to repair his damaged relationship with Macaulay, and had reportedly made overtures to his estranged son before the stroke apparently sidelined that plan. 

Kit spoke with the Daily Mail in 2016, and shared some harsh words about Macaulay that pretty much defined the state of their relationship. "I don't consider him a son anymore," Kit coldly said of his third-born child, confirming the bad blood between the two had lingered on over the years.

In 2022, RadarOnline reported that Kit had made some attempts to meet his son's first child, son Dakota, whom the actor shares with Brenda Song. Culkin, however, reportedly rebuffed that overture and refused to let his dad anywhere near his son. When the "Home Alone" star received his own star on the famed Hollywood Walk of Fame in December 2023, it was telling that his father was not among the attendees.