If you were a kid in the ’90s, chances are you grew up watching A LOT of Macaulay Culkin movies.

Maybe you watched “Home Alone” every Christmas, cried your eyes out during that certain bee scene in “My Girl,” or dreamt of visiting a magical land full of literary characters like in “The Pagemaster.”

Any way you split it, Macaulay Culkin (or “Mack,” as he prefers) remains the paradigm of nostalgia personified for many millennials.

The “Home Alone” star has been famous for over 30 years, so naturally, we’ve seen him grow and change a lot over the decades.

The little boy who slapped his face with aftershave lives on in the pantheon of pop culture icons, but there are plenty of other Culkin moments that are nearly as memorable, like when he played a glammed-out character in “Party Monster,” his long-haired hipster phase, or when the lovable eccentric was caught by the paps walking his cat in a stroller while wearing a shirt that read “emotional support human.”

From “Home Alone” to the Gucci runway, let’s take a look at how the child star has transformed over the years.

Macaulay Culkin grew up in NYC

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Macaulay Culkin was born in New York City in 1980 and was the third oldest of seven children. “My mom didn’t have a family. She had a litter,” he joked on “The Ellen DeGeneres Show.”

“We grew up in a one-bedroom apartment in Manhattan. …We lived on top of each other. … We were a close-knit family because of that,” he explained.

A few of his siblings, most notably Kieran Culkin, have gone on to have solid showbiz careers as well.

Their father, Kit, was an actor and dancer and encouraged his children to pursue dance and theater at a young age. Once Macaulay began getting roles, his parents became his managers.

While he was close with his mother and siblings, his father was allegedly abusive.

Macaulay said they had always disliked each other, and he speculated that jealousy played a part in his father’s cruel tendencies.

He said on “WTF with Marc Maron,” “Everything that he tried to do in his life, I excelled at before I was 10 years old.”

Macaulay added, “He was abusive, physically and mentally.

… I can show you all my scars.” Even though he hasn’t spoken to his father for decades, he said, “I have forgiveness in my heart.”

His first roles were on stage

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Off-Broadway theater was Macaulay Culkin’s first foray into the arts and entertainment business.

The “little sailor boy” in a production of Gilbert & Sullivan’s “H.M.S. Pinafore” was one of his earliest roles, he revealed to Marc Maron on “WTF.”

Culkin made a rapid transition to the screen, appearing as a guest star in the TV series “The Equalizer” in 1988.

That same year, he also made his film debut in “Rocket Gibraltar.” But his breakthrough role was in the 1989 John Hughes film, “Uncle Buck,” starring John Candy.

“I was very lucky. I started booking movies kind of right off the bat. … Billy Hopkins, who was a casting director, he actually directed me in some of that black box theater kind of stuff. He also did a lot of John Hughes things. … So then, boom, ‘Uncle Buck’ happens, and, you know, s*** rolls downhill,” Culkin explained to Maron.

At the same time, he was also entering the ballet world. At the age of 8, he was accepted into the School of American Ballet and played the role of Fritz in the New York City Ballet’s “The Nutcracker” for the 1988 season, per The New York Times. “I was almost a ballet dancer first for a while there.

Like I’d go off and do ‘Uncle Buck,’ and then I’d turn around and go back home to do ‘The Nutcracker’ at Lincoln Center,” he said on “The Ellen DeGeneres Show.”

The unexpected success of Home Alone

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“Home Alone” is the film that solidified Macaulay Culkin’s place as one of the most famous child stars ever. The role was practically written for him.

John Hughes, who had been responsible for a number of ’80s teen hits, including “The Breakfast Club,” “Sixteen Candles,” and “Ferris Bueller’s Day Off,” came up with the idea of “Home Alone” shortly after “Uncle Buck.”

Hughes explained in an interview with Bobbie Wygant, “[Macaulay Culkin] was in the back of my mind. I had just finished ‘Uncle Buck’ and I had a wonderful experience with him there.

He was a great deal of fun to work with.”

The casting director, Janet Hirshenson, did a quick search to make sure Culkin was the right fit for the role, but “there wasn’t anyone better than Macaulay,” she said in an interview with Independent.

The director, Chris Columbus, added, “No one else had whatever quality Mack had. He felt like a real kid but was also incredibly charming and extraordinarily funny … Mack was slightly imperfect too, which was great.

One ear was kind of bent, he didn’t look like other kids — but everyone who met him fell in love with him and for me, that’s a movie star.”

“Home Alone” was a low-budget film that surprised everyone with its massive success.

It went on to become the highest-grossing John Hughes movie, the highest-grossing comedy of all time, and the third highest-grossing movie ever at the time.

The actor’s rise to mega stardom

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After the runaway success of “Home Alone,” Macaulay Culkin went on to become the biggest little movie star of the early ’90s. Movie studios trying to cash in on the popularity of the young actor flooded him with job offers.

“I did like 14 movies in six years or something like that,” he said in an interview on “The Ellen DeGeneres Show.”

Those movies included “My Girl,” “Home Alone 2: Lost in New York,” “The Good Son,” “Getting Even with Dad,” “The Pagemaster,” and “Richie Rich.”

His movie paydays increased accordingly. According to Celebrity Net Worth, he went from a $100,000 salary for “Home Alone” to making $1 million for “My Girl.”

He brought in $4.5 million for “Home Alone 2,” and by the time he filmed “Richie Rich,” he was getting paid $8 million per movie.

Even more exposure was inevitable. He hosted SNL in 1991 at the age of 11, becoming one of the series’ youngest hosts ever. The worldwide fame that followed made for a difficult childhood and a loss of privacy.

“I really couldn’t remember a time when people weren’t gawking at me and there weren’t people in the bushes with cameras,” he said on “The Tonight Show.”

His friendship with Michael Jackson

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During the dizzying heights of his early 1990s fame, Macaulay Culkin considered Michael Jackson his closest friend. “He was my best friend growing up,” he explained to Marc Maron on “WTF.”

Culkin spent a lot of time hanging out with Jackson at Neverland Ranch and appeared in his music video, “Black and White.”

According to Culkin, Jackson reached out to him as a former child star trying to look after other child stars.

On the podcast “Inside of You with Michael Rosenbaum,” he explained, “I mean at the end of the day, it’s almost easy to try to say it was weird or whatever, but it wasn’t, because it made sense.

… I was a peerless person. … and he was the kind of person who’d been through the exact same frickin’ thing and wanted to make sure that I wasn’t alone.”

Culkin said the “King of Pop” was a “sweet” and “hilarious” BFF and added, “It was a normal friendship.”

In 2005, Culkin came to Jackson’s defense against sexual abuse allegations.

He told New York Magazine that he “didn’t want to get involved with the whole thing,” but after two of Jackson’s former employees testified they had witnessed Jackson molest Culkin when he was a child, he gave a testimony in the trial, which played a huge part in Jackson’s exoneration at the time. They remained friends until the pop star’s death in 2009.

Culkin serves as godfather to Jackson’s children, sharing matching tattoos with Paris Jackson.

Macaulay Culkin temporarily retired at 14

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“Richie Rich” was Macaulay Culkin’s last movie as a child actor. Weary of show business at 14, he made the decision to live life out of the spotlight for a while, go to high school, and make friends who were the same age as he was.

“I was tired of it, to be honest. … I needed to grow and develop as a person,” he said in an interview on “The Ellen DeGeneres Show.”

At the time, his parents, who had never been legally married, were separating and in the midst of a costly legal battle for custody of their children.

“After I did ‘Richie Rich’ … and then my father and my mother finally called it quits,” he explained on “WTF,” “I was able to actually walk away from the business. … I just was like, ‘I’m done. I’m done guys. I hope y’all made your money because there’s no more coming from me.”

But all that money — and we’re talking millions — was sitting in a bank account with his parents’ name on it, not to be touched until he was 18.

In order to protect his money, Culkin had to make some pretty serious financial decisions before he was old enough to drive.

In an interview with Esquire, he explained, “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.”

Macaulay Culkin married Rachel Miner when he was 17

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During Macaulay Culkin’s time away from the limelight, he attended high school at The Professional Children’s School in New York City.

While there, he began dating a fellow classmate and actor, Rachel Miner, who had appeared on the soap opera “Guiding Light” in the early ’90s.

She went on to star in films, including “Bully” in 2001, followed by a television career, playing prominent characters in “Californication” and “Supernatural,” among others.

The two teenage actors were “high school sweethearts” and “loved each other very much,” Culkin explained on “The Tonight Show.”

“This is how we decided to convey our love — we got married,” he said.

They were only 17 when they tied the knot. According to Culkin, Miner had already broken up with him three times before he popped the question.

“I pinned her down and said, ‘Okay, marry me now before you break up with me again,’ so she did,” he recalled, noting he didn’t actually physically pin her down.

But this teenage love story came to an end a couple of years later. Culkin and Miner separated in 2000 and officially divorced in 2002.

He returned to acting when he was 20

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After six years away from acting, Macaulay Culkin was ready to dive in again. His comeback began in 2000 on a London West End theater stage, starring in “Madame Melville,” a play about a student who is seduced by his teacher.

He told BBC News, “As a senior in high school you figure out what you want to do with your life.

I asked myself if I wanted to get back into acting and thought: ‘Yes but under my own terms and nothing like it was before.'”

He decided to be very selective about what projects he works on. “I am not revving to do a big Hollywood comeback. All I want is to do good things with good people.

It doesn’t matter if it is a play or film. I just want to do my own thing,” he also stated in the BBC interview.

The 2003 true-story club-kid drama, “Party Monster,” fell under that category for him.

The low-budget film, which also starred Seth Green, Wilmer Valderrama, Chloe Sevigny, and Dylan McDermott, was met with mostly unfavorable reviews (it holds a 29% fresh rating on Rotten Tomatoes) but gained a cult following and has arguably earned its place as a camp classic.

That same year, Culkin made a comedic return as a guest star on “Will & Grace.” In 2004, he starred alongside Mandy Moore and Jena Malone in “Saved!,” a well-received teen comedy about a Christian high school.

He was arrested in 2004

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In 2004, Macaulay Culkin was arrested for drug possession.

After he and a friend were pulled over for speeding, the police found marijuana, as well as Xanax and clonazepam that he didn’t have a prescription for, reported CNN.

The arrest, Culkin believed, was blown way out of proportion.

“You know, I am a former child actor … I’m supposed to be a lot more f***ed up than I am.

I took a certain amount of pride that I wasn’t that cliché, so it was, like, ‘Oh, great, I gave a lot of people exactly what they wanted,'” he told New York Magazine.

In reality, he wasn’t the partying, drugged-out former child star everyone assumed him to be after his arrest.

When Larry King asked him about his drug use, he said, “Everything that I do, for some reason, becomes this big crazy thing, you know, even though any normal person does it.

Like, yeah, I’m a kid. I had a beer, I smoked a joint. Big deal. … I never had a problem.”

But gossip about drug addiction persisted for years. In 2012, rumors swirled that Culkin was addicted to heroin, according to Reel Chicago.

He assured The Guardian in 2016, “No, I was not pounding 6 grand of heroin every month or whatever.

The thing that bugged me was tabloids wrapping it all in this weird guise of concern. No, you’re trying to shift papers.”

He published a novel in 2006

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In 2006, Macaulay Culkin published a book called “Junior.”

Part novel, part memoir, the book is an assortment of story fragments, snippets, drawings, and poems.

He may have written a book, but his introduction plainly states, “I am not a writer.”

He proceeds to explain, “I’m not trying to pass this book off as something it is not. This is just a bunch of stuff I put together and someone said ‘Hey, you should write a book,’ so I did.”

Critics of the book were a little harsh. For instance, Publisher’s Weekly called it a “self-indulgently infantile book.”

But Culkin was already mentally prepared for that kind of labeling.

“I’m not expecting the American literary community to welcome me with open arms. To them I’m just some schmuck kid who wrote some book,” he told New York Magazine.

Despite the haters, Culkin said he was proud of putting it out into the world.

“The whole experience is frightening because I’m putting my words out there in a way that can just be twisted … [but] it’s a great process for me.

… I’m totally scared to death doing it, but then when I come out the other end of it, I’m so glad that I did it,” he told Conan O’Brien in an interview promoting the book.

Macaulay Culkin was in an 8-year relationship with Mila Kunis

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When Macaulay Culkin started dating Mila Kunis in 2002, she was 18 years old. He was 21.

The couple stayed together for 8 years. “We’re incredibly private … We like to read books or play video games or watch TV or go to the movies. And he’s an amazing cook. He makes dinner every night,” Kunis told Parade in 2007.

Explaining that Culkin is very different from how the media often tries to portray him, she called him “so sweet” and said, “There are a lot of things people want him to be that he’s not.

He’s an amazing, simple guy, who is probably the most brilliant person I’ve ever met.”

Though they both became famous at a very young age (Kunis was only 14 when she started working on “That ’70s Show”), Culkin’s fame must have made keeping their private lives out of the spotlight difficult.

“You couldn’t walk down the street with him,” Kunis told Howard Stern. “Like fans just screamed … they didn’t know how to react. It wasn’t like a normal response to a celebrity. Fans responded in a very abnormal way to him.”

Kunis called their breakup “horrible” and told Dax Shepard on “Armchair Expert” that the split was her fault. “I f***ed up. I was an a**hole in my 20s, and I’ll be the first to admit it. … It’s f***ed up what I did and f***ed up how I did it,” she confessed.

Read More: https://www.nickiswift.com/772357/the-transformation-of-macaulay-culkin-from-childhood-to-41/

He formed Pizza Underground in 2013

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In 2013, Macaulay Culkin began focusing a lot of his time on a Velvet Underground cover band called Pizza Underground. The band changed lyrics of Velvet Underground songs to make them into songs about pizza.

“It was a lark that we did. … we recorded something in my living room … then just put it online and kind of forgot about it,” he explained on Marc Maron’s podcast, “WTF.”

The “lark” went viral shortly after. Before their first show at Baby’s All Right in Brooklyn, Culkin and his bandmates were shocked to find a “line four-people wide around the block,” he recalled to Maron.

“We kind of hit that hipster strike zone … The Brooklyn hipsters freaking love that kind of thing,” he added. What started as a joke ended up taking off, and they went on several tours.

Believe it or not, Lizzo was the opening act on their tour. Lizzo and Macaulay Culkin have been friends for nearly a decade (he even made a guest appearance in Lizzo’s “Faded” video in 2014).

In 2019, Culkin interviewed his old pal on his podcast, “Bunny Ears,” and they reminisced about their simpler Pizza Underground days.

“It’s one of the more embarrassing things to say, is that Lizzo opened for Pizza Underground,” Culkin said. “We were not anywhere near your level even then.” Lizzo responded, “What do you mean?

The pizza box was a drum. … It was incredible.” Lizzo would also sing a song with them every night about “a sexy pizza man.”

The actor started living in Paris in 2013

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In 2013, Macaulay Culkin relocated to Paris. One of the many reasons he liked Paris was because he wasn’t gawked at in public as much. He told Marc Maron on “WTF,” “I thought nobody recognized me, and what it was was, ‘No, we recognize you.

We just don’t care.’ … I was like, ‘Where have you people been my whole life?'”

He was friends with a group of musicians and artists who lived there, including Pete Doherty.

“During one of my trips, [my friends] said, ‘When are you going to move out here?’ and I said, ‘How’s next week?’ … and I’ve been living in Paris for the last four years,” Culkin told Maron in the 2018 interview.

He jokingly added, “I’m a 30-something retired person … walking around with a baguette tucked under my arm. I’m living the romantic life.”

He vibed with the way Parisians live their life. “It’s a special place,” he said on the “The Joe Rogan Experience,” “Food and wine is fantastic.

The girls are pretty. It’s the leisurely lifestyle … I like their eating habits.” But his French living didn’t last forever.

He revealed on “Bunny Ears” that he had sold his apartment in Paris in 2019: “I lived there for like five years or something like that but I eventually had to give it up.”

He cited his girlfriend, Brenda Song, as the reason, saying, “I have a lady. … I’m Mr. Suburban Domesticated.”

Macaulay Culkin began dating Brenda Song in 2017

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Macaulay Culkin met Brenda Song, a former Disney Channel star, in 2017 on the set of “Changeland,” a movie directed by Culkin’s longtime pal Seth Green.

The pair instantly bonded over entering show business at an early age.

“Child actors, we don’t even get to talk about it, you just look each other in the eye and you nod and we know,” Song told ET.

A romance soon sparked between the two former child stars. In its 2020 cover story on Culkin, Esquire wrote that when he first started dating Song, “the feeling that it was too good to be true almost overwhelmed him.”

Song was just as smitten. She told the publication, “People don’t realize how incredibly kind and loyal and sweet and smart he is. Truly what makes Mack so special is that he is so unapologetically Mack.

He knows who he is, and he’s 100 percent okay with that. And that to me is an incredibly sexy quality. He’s worked really hard to be the person he is.”

The couple has one child together, Dakota, who was born in April 2021. On January 26, 2022, People reported that Culkin and Song were engaged.

He launched Bunny Ears in 2018

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Macaulay Culkin branched into another realm of entertainment when he started Bunny Ears.

The website features satirical articles and a Culkin-hosted podcast. He described it as “Goop meets The Onion” on “The Tonight Show,” while the website’s “About Us” page says it’s “a world-class comedy brand created in 2017 when former Pagemaster Macaulay Culkin woke up from his long slumber (fondly referred to as the ‘Culkin-Sleep’), took a hard look at the Internet, and realized it was all pretty sh**ty.”

His aim was to bring a little bit of quirky sunshine to the dark and mean crevices of the internet.

Bunny Ears editor, Shawn DePasquale, told Dazed, “The internet can be as wonderful or as awful as you allow it.

We’re looking to contribute to the positive side of the internet.

We want to be one of those sites that puts out content that reminds people, ‘Oh s***. The internet is f***ed up and weird as hell, but I love it.'”

Some of Culkin’s personal favorite articles include “The Beginner’s Guide to Regretting Buying That Turtle” and “The Beginner’s Guide to Faking Your Own Death” because they are “humorous yet informational, and that’s what Bunnyears.com is all about,” he told Dazed.

Macaulay Culkin is happy and living a ‘full life’

Esquire
Macaulay Culkin doesn’t actively pursue acting anymore, though he’ll occasionally do things if they interest him.

After making a number of high-grossing films when he was a kid, Culkin is pretty much set for life money-wise, considering his net worth, which  Celebrity Net Worth lists as $18 million.

In a 2018 interview with Ellen DeGeneres, he said, “I felt like some kid worked really, really hard and I inherited all of his money … It allows me to treat everything like a hobby.”

And he’s happy with that. “I live a very rich, full, silly, life.

And I wouldn’t have it any other way,” he said on the “WTF” podcast.

As far as the past goes, he’s not bitter about any of it and, in fact, is as grateful as grateful can be.

“Certain f***ed-up things happened, but f***ed-up things happen to kids all the time and they don’t come out the other end.

I’ve got something to show for it … I got money, I got fame, I got a beautiful girlfriend and a beautiful house and beautiful animals. … I want for nothing and need for even less,” he told Esquire.

He also maintains a healthy dose of humor surrounding his childhood fame and, after all this time, still knows he has a special place in many people’s nostalgia.

On his 40th birthday, he tweeted, “Hey guys, wanna feel old? I’m 40. You’re welcome.”

The tweet went viral and became one of the most liked tweets ever.

He went back to acting again

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Ever in and out of retirement, Macaulay Culkin returned to acting in 2021 for the 10th season of “American Horror Story.” His character, Mickey, quickly became a fan favorite.

Culkin’s co-star Leslie Grossman told E! News that “it was an absolute joy to work with Macaulay” and said she was impressed with his “vulnerability” as an actor.

His stint on “AHS” proved once again that Culkin has a lot to give as an actor and that fans are as happy as ever to see him lighting up their screens.

In 2021, Culkin was also spotted walking in Gucci’s “Love Parade” fashion show. Because of his tendency to shy away from Hollywood events, Vogue reported, “The arrival of former child star Macaulay Culkin was something of a plot twist.” But 2021 found Culkin slowly returning to life in the public eye. And there was more to come.

In February 2022, Deadline reported that Culkin had a television series in the works called “Macaulay Culkin’s Midlife Crisis.”

Producers Jonathan and Simon Chinn told the outlet, “Despite [Macaulay Culkin’s] legendary status, like the rest of us he’s having to confront what it means to be a normal middle-aged guy, with a wife and a new kid who’s soon going to be the same age he was when he became a massive global superstar.

We are thrilled to be working through our mid-life crises with him on this exciting project.”

Sounds like some much-needed comfort content for ’80s and early-’90s kids.