20 Pics Of Macaulay Culkin Growing Up (And 5 Of His Forgotten Brother)

Being a ’90s kid meant falling in love with the story of a boy who was left at home while his family went on Christmas vacation. Instead of crying and being worried, he was thrilled. He ate junk food galore and even stood up to some jerks who were trying to break into his house.

Of course, we’re talking about the iconic movie Home Alone. The film led to three sequels, but like most things, the first one is the greatest, and it’s still talked about and watched by families every holiday season. The movie made a star out of a then-10-year-old Macaulay Culkin, who became known as one of the child stars who had some unfortunate times.

Now Macaulay Culkin is 38 years old and seems to be doing well. He’s in a relationship with actress Brenda Song, and people say that he has made a home in Paris, France.

Many of his oldest fans today have probably shown their little ones Home Alone and consider Macaulay Culkin to be a big part of their childhoods. Let’s look at some adorable photos of him as a kid. Here are 20 pictures of the child star while he was growing up, along with five of his forgotten brother.

25 We’re Swooning Over How Cute Young Macaulay Is

via Pinterest

This is an incredibly iconic outfit from the ’90s. If someone was curious about how children used to dress during that decade we could offer this pic up. Macaulay looks so cute in baggy jeans, big white sneakers, and a sporty top. We also love his bangs.

When we look at photos of Macaulay as a kid, we can’t help but think that he looked really innocent. We would have no idea that he became so famous and that he had so many problems because of that.

24 We Love This Pic Of The Child Star With Young Brooke Shields

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Doesn’t the woman on the left look super familiar? Well, that’s Brooke Shields. Her big hair proves that this photo must have been snapped in the late ’80s or early ’90s.

We really can’t even when see the baggy jeans and jacket that Macaulay is wearing. The jacket is especially awesome. Check out the baseball pattern on it. If we have boys, we bet that they would want this jacket for themselves (even if baggy clothing isn’t quite in style anymore).

23 He’s Walking Around With Ex-Girlfriend Mila Kunis (And They Made Such A Cute Couple)

via Hip Daily

Did we know that Macaulay Culkin and Mila Kunis were in a relationship for a while? They were together for eight years, from 2002 until 2010, which is definitely a long time. This photo was taken during their relationship, and it’s nice to see them walking. It’s a very regular kind of photo.

According to Entertainment Tonight, she said that the breakup was her fault. She continued, “You know, it’s been so long, like I feel like enough time has gone by. I think enough mutual friends have been like … everybody kind of forgave everybody for what went down. “

22 And He Looks Cute In This Snapshot With Mila, Too

via Us Weekly

This is a really nice photo of Mila and Macaulay, and they both look so young here. Mila’s green T-shirt is particularly adorable.

In the same interview with Entertainment Tonight, Mila talked about how famous Macaulay is: “He was huge. You couldn’t walk down the street with him. He always had this weird attraction, like fans just screamed when they saw him! 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.

21 Macaulay Looks Adorable In A Tiny Red Sporty Jacket, Pictured Here With His Family

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What mom doesn’t want to get a jacket like the one that Macaulay is wearing in this photo for her son? Those red sporty jackets really are always in style. And even if someone told us that they weren’t in style anymore, we would have to say that they totally are. There’s a retro, 1950s charm to them.

Macaulay looks adorable in this photo of him and his parents, but unfortunately, it seems like it wasn’t a great family life. According to The Daily Beast, “In the early ’90s, rumors began surfacing that Macaulay’s manager-father, Kit Culkin, had been stealing money from his child star-son so, after a bitter custody battle, the court sided with his mother and Macaulay subsequently fired his father.”

20 He’s Cute As A Button In A Blue Baseball Cap In 1988

via Buzzfeed

Here Macaulay is wearing a blue baseball cap back in 1988, which would have made him around eight years old when this photo was taken. There is something so cute about a kid wearing a baseball cap. Maybe because we automatically picture a kid playing baseball… and that is even more adorable.

It looks like the actor has got a white T-shirt and some striped navy and white overalls on, which is another reminder that this photo was taken right before the ’90s when that fashion was so popular.

19 The Child Star Has Got A Wide-Open Grin In This Early Picture

via LifeBuzz

If a ’90s kid wasn’t wearing plaid at least sometimes, they were probably in the wrong decade. We love seeing this photo of Macaulay Culkin in a red and blue plaid shirt.

According to The Hollywood Reporter, when Macaulay appeared on The Jimmy Fallon Show, he talked about the Home Alone moment when he saw the Rockefeller Center tree. He said, “I had to work at 4 a.m. as a 10-year-old. It was great. It was my favorite day as a child.” We’re sure that it wasn’t super glamorous to film movies and be a child actor, even if we think that it might be.

18 This Pic Is Around The Time Of His Movie ‘My Girl’

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While moms will definitely jump to show their kids Home Alone, the same might not be said of the movie My Girl. Honestly, this is an incredibly sad movie, and there is one scene featuring Macaulay Culkin’s character that makes it really emotional to watch. (If we’ve seen it, we know that scene. It’s too much to talk about.)

We might want to wait until our kids are a bit older before showing them this particular movie, but in the meantime, we can say that this photo of Macaulay that was taken around the time of the movie is great. His hair is super messy and those glasses are so cute and chic.

17 Now Macaulay Is Looking Super Serious (And We Love His Dapper Suit)

via OnBites

It’s not often that we see a photo like this of a kid. Macaulay is wearing the kind of outfit that we typically see when kids attend private school. It totally looks like a uniform, right?

The only word that comes to mind is “dapper” so we would have to describe the child actor that way. We love his slicked back hair. The photo is an interesting contrast to other ones that we’ve seen where he looks like a carefree child. #RichieRich

16 We Can’t Get Over The Star’s Amazing Blonde Hair, Which Was Sometimes Long And Sometimes Shorter

both images via Pinterest

When we see photos of Macaulay Culkin growing up, we definitely notice that in some cases, his hair is really long and in others, his hair is much shorter. We wonder if he was the kind of kid who dislikes getting his hair cut… which is probably the way that most children feel about it?

It’s cool to see the contrast in his hairstyles: on the left, he’s got a really short style and we can see his ears, and in the photo on the right, his hair is long and sweeping and almost down to his shoulders.

15 We Love His Oversized Purple ‘Home Alone 2’ T-Shirt In This Throwback Pic

via India Today

It’s really cool to see the Home Alone star in this branded T-shirt, and we love that it’s bright purple.

This is a true throwback picture and reminds us that while we focus on the first movie, the sequel does have a lot of merits. After all, this is the movie when Macaulay is let loose in New York City. He stays in a hotel, frequently visits a toy store, and learns a lot of lessons. Our kids would be in heaven eating as much candy as he does in these movies, right?!

14 Here He Is Looking Too Cool For School

via The Mercury News

“Too cool for school” is totally the vibe that we’re getting from this photo of Macaulay Culkin from when he was growing up. This red jacket looks really similar to the one that he was wearing in the photo with his parents.

The actor looks super confident, leaning against what looks like a waste bin or maybe a newspaper box, and that stance honestly makes him look like a teenager. He was still pretty young in this photo and not yet at the teen stage, though.

13 Now He’s Looking Cool In A Michael Jackson Music Video In 1991

via Daily Mail

In 1991, Macaulay Culkin was in the music video for Michael Jackson’s song “Black or White.” George Wendt, the Cheers actor, and Tess Harper (who we might know from her role on Breaking Bad) were also in the video.

Macaulay looks very cool in this photo, wearing a baggy red sweatshirt and what looks like massive shoes, along with a huge gold money sign necklace. It’s definitely a different look from the kid that we’ve seen in the other photos from when he was growing up.

12 Macaulay’s Being Hugged By His Parents In 1990

via Independent.ie

This photo of Macaulay and his parents was taken in 1990, which would have made him around ten years old. Of course, now we know that he didn’t have the greatest relationship with his dad, so we do feel pretty emotional when seeing old pictures of the family. It would be a few years before his parents got divorced in 1994.

According to a Vanity Fair profile of Macaulay’s brother, Kieran Culkin, the brothers don’t talk to their dad anymore: “But life with their father, Christopher Cornelius ‘Kit’ Culkin, was not so wonderful. Kieran and Mac have no contact with him.

11 Now He’s At SNL With Rob Schneider In 1991 (Which Would Be A Big Deal For Any Kid)

via Mercury News

Whether we watch Saturday Night Live regularly or not, we can admit that it would be really cool to attend a taping of the show. And if we got to go backstage? That would definitely be awesome.

Macaulay was even luckier: he wasn’t in the audience or backstage… he was actually on the show. He appeared on the iconic series in November of 1991. Here he is with Rob Schneider and the expressions on their faces are so happy and cute.

10 Here Macaulay Is Looking Cute In All Black With Rachel Miner (To Whom He Was Once Married)

via Buzzfeed

In 1998, Macaulay Culkin and Rachel Miner got married, only to get divorced a few years later in 2002. This is a photo of the couple back when they were together. Rachel’s dress definitely has some Romeo and Juliet vibes which makes sense given the time period. (It was a very late-’90s, early-2000s thing to wear those types of slip dresses.)

Rachel Miner was a successful actress but left the business. Today, she works for a nonprofit, Random Acts, and is the Executive Director.

9 Macaulay Is Grinning In This Sweet Pic

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People often say that if we’re in a bad mood, we just need to pretend to smile and then the act of smiling will cheer us up completely. Maybe that’s true or maybe not… but we can probably say that seeing photos of people with big grins on their faces cheers us up.

This photo of Macaulay is definitely very cheerful. Even though he took a break from Hollywood, Macaulay did really well as a child: Vanity Fair says that he was “the first child actor to be paid $1 million, for his role in My Girl, as well as the second-youngest celebrity to host Saturday Night Live, at age 11.”

8 Here Is Getting A Bit Older (And His Blonde Hair Is Growing A Bit Longer)

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In this picture, Macaulay looks like he was probably a pre-teen, and we can see that he was growing up. His hair was getting longer and falling over one eye which is a total teen heartthrob kind of look.

Macaulay was in many movies when he was a kid and after 1994, he didn’t appear in any movies for around a decade. People say that he came back from his break with a role in the movie Party Monster which came out in 2003.

7 Now He’s Growing Up For Sure (And Looks Like A Teen Idol)

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Can we say “teen idol”?! It would be tough to describe this photo of the actor in another way.

It makes sense that Mila Kunis would say that people would always go pretty nuts when they saw Macaulay. While we would like to think that we would be more dignified if we ever ran into him in public, well, we’re such big fans of Home Alone that we might embarrass ourselves. (And we would definitely embarrass our kids… Oops.)

6 Here Macauley Is Looking Happy And Like Any Other Kid (And We’d Never Guess He Was A Massive Child Star)

via Metro

Here’s another photo of Macaulay Culkin growing up where he doesn’t look like the massive child star that he was about to become. He looks happy and like any other kid.

When we think about the actor, we’re probably wondering how he feels about Home Alone. According to Vanity Fair, he was on The Ellen DeGeneres Show and he told Ellen, “I don’t really watch them all that often.” He continued, “It’s background radiation at Christmastime. I’ve had people who want to sit down and watch it with me, which is both flattering and …” well, in so many words, uncomfortable.

We’re totally those people who watch it every Christmas…

And here are five photos of his forgotten brother…

5 Macaulay And Kiernan Look Like Little Grown-Ups In Tuxes Back in 1991

via HuffPost

While everyone knows the Home Alone star, Macaulay does have two brothers: Kieran and Rory. Kieran could definitely be called “the forgotten Culkin brother” as he is an actor, too, but he isn’t talked about as much.

This is a photo of the brothers from 1991 and we really enjoy seeing them in these tuxes. Macaulay looks like the proud and confident older brother and Kieran looks a bit more nervous. There are only two years between them, as Kieran is 36 and Macaulay is 38.

4 Kiernan Culkin Looks Smart And Bookish With Wild Hair And Glasses

via Wall of Celebrities

Is that Kieran Culkin or Harry Potter? We can’t help but ask ourselves that question after seeing this great picture of the actor as a kid.

We love his bookish glasses, the old book in front of him, his plaid shirt, and his really messy hair. While his brother Macaulay was often very put together as a child and had very smooth hair when he was photographed, Kieran sometimes had messier hair like when this photo was taken. Actually, Kieran was in the first Home Alone movie and played Fuller, Kevin’s cousin.

3 And Here’s Another Sweet Brotherly Moment

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What a sweet brotherly moment… and Macaulay is wearing another amazing jacket. This time, it’s red and blue.

It sounds like the siblings are still close: as Emily Gerson Saines, Macaulay’s manager, said in the Vanity Fair story about Kieran, “We all just recently went to Rory’s wedding, and it was so incredible, because Kieran was there with his wife, and Macaulay was there with his girlfriend, and the women all get along really well. It just melts my heart to see them all together like that.”

2 We Might Not Remember Now That Kiernan Was In ‘Father Of The Bride’ (But He Looked Adorable)

via Redbook

Kieran was also in the 1991 film Father of the Bride, and this is a photo from that movie. It’s so sweet to see him with Steve Martin. This is honestly a super 1990s photo with the turtleneck and the plaid and just the styles in general.

Kieran might not be as famous as Macaulay and he wasn’t talked about as a “child star” the way that his brother was, but he has been very successful in movies. He was also in She’s All ThatFargo, and he has more recently been in the HBO series Succession.

1 And Now He’s Getting Into The Pre-Teen Stage

via Fandom

Kieran Culkin looks like he’s a pre-teen in this photo and he looks like a very regular guy.

It sounds like Kieran took a break from acting after appearing in a lot of movies as a kid: he told Backstage that when he turned 20 years old he went on a hiatus. He said, So I took a lot of time to try to figure out if it was what I wanted to do. But then, in the meantime, I kept doing only jobs that I really wanted to. A lot of that was theater.”

It’s cool to hear that he found what he loves to do, which is what we all want to hear our kids say.

Sources: Huffpost.com, Vanityfair.com, Thedailybeast.com, Hollywoodreporter.com, Etonline.com, Vanityfair.com, Backstage.com