Macaulay Culkin and Ryan Gosling once shared an epic social media moment

Actors Macaulay Culkin and Ryan Gosling have made significant strides in Hollywood. Macaulay rose to fame as a child in the first two Home Alone movies, and has been riding the wave from those classics ever since. Before becoming the Ken to Margot Robbie's Barbie, Ryan also dabbled into childhood stardom with The Mickey Mouse Club. If you haven't heard him singing Jodeci's "Cry For You" with a pre-N'Sync Justin Timberlake and JC Chavez, watch it immediately after this read!

In addition to both being involved in the entertainment business as children in the '90s, Ryan and Macaulay both have wives who are actors and also understand the business — Eva Mendes and Brenda Song, respectively. However, despite their similarities, many want to know if they're friends.

Ryan and Macaulay don't appear to be friends. However, they have shared experiences and were randomly connected at one point in pop culture history when The Notebook star helped put the My Girl actor on Hollywood's radar again.

In 2013, years after Macaulay decided to quit acting, Ryan honored him with a dose of nostalgia. He posted a photo of himself wearing a T-shirt of the former child star during his Home Alone era. The black-and-white image showed Mac pretending to choke himself with a Life Magazine logo on the front right side of the shirt. Ryan was spotted wearing the shirt while walking outside. According to a report of the sighting from Elle in 2014, him wearing a shirt with Macaulay's face on it made the actor, who had been away from the spotlight, "instantly cool again."

In May 2014, the Party Monster star expressed his appreciation for Ryan by posting his own ode to his peer. Macaulay posted a snap of him rocking long hair and sunglasses as he wore a t-shirt of the photo of Ryan wearing the t-shirt of his photo. If that was confusing, no worries. We have the images below.

While they don't seem to be friends with each other, Macaulay and Ryan have been in the industry around the same time. Throughout their time in the limelight, they've made plenty of celebrity friends. According to E! News, some of the celebs Ryan calls his homies, including his longtime co-star Emma Stone, John Legend, and Bradley Cooper. Emma shared how much her "dear, wonderful friend" and leading man's friendship has meant to her over the years.

"I can't even imagine what my life would be without Ryan," she said. "He's so special. It makes me emotional."

Macaulay has also had some pretty famous friendships in his lifetime. Some of the celebrity friends he made during his childhood included Michael Jackson, who died in 2009, and Elijah Wood. In recent years, Macaulay has bonded with fellow '90s actor Freddie Prinze, Jr. In August 2024, the former teen heartthrob reflected on playing a video game with Mac, where he discovered how much trash he could talk.

"I play the [video] game BattleTech with Macaulay Culkin," Freddie told People. "He’s a very good s--t talker. He said something very funny to me about one of the other players. I can’t even say what it was, because that guy will see this and know it was him."

Although Macaulay and Ryan haven't linked up yet, there's always time!