Macaulay Culkin Worried ‘Something Bad’s Gonna Happen’ Before Falling For Brenda Song

Jun 13, 2022

Macaulay Culkin, 41, is most famous for his role as Kevin McCallister in the blockbuster Hollywood film "Home Alone." As a child, Culkin already had two "Home Alone" movies under his belt, and he starred in 15 films in just a mere seven years. The Hollywood cutie was a busy, successful actor from such a young age, but starting in his teenage years, he experienced his fair share of ups and downs.

He told Esquire in 2020, "I played with some fire, I guess is the best way to put it." Alongside a troubled youth, where despite being incredibly famous, Culkin shunned the spotlight, he also had to deal with the losses of people close to him, including his sister, who died after being struck by a car in 2008.

Romantically, Culkin also had a tough time. After he married his first love, Rachel Miner at the age of 18, the star eventually divorced and later entered into a nine-year relationship with Mila Kunis. Although it seemed they were in it for the long haul, their romance ended in a "horrible, horrible breakup." Kunis admitted on Dax Shepard's podcast Armchair Expert that she was to blame. She said: "And it’s f***** up what I did. It’s f***** up what I did and it’s f***** up how I did it."

But after a tough period, Culkin began to get back on his feet. He went on to pursue other passion projects, such as singing in a rock band, and eventually, he returned to acting. He even revived his “Home Alone” character Kevin for a Google assistant advertisement. 

What's more, he found love again and could finally let his guard down after being hurt in his previous relationship. Culkin began dating Brenda Song in 2017 and in 2021, the couple had their first child together before announcing their engagement in Jan. 2022.

The story of Culkin's life from child superstar to troubled young adult is no secret. One of seven children, Culkin lived a modest childhood when his acting career began at the tender age of 4. The "Home Alone" star started with small parts in off-Broadway productions before working himself up to more prestigious gigs, including the "Bach Babies" at the New York Philharmonic. Although Culkin landed role after role in New York, his family still struggled financially.

Billy Hopkins, the casting director to give Culkin his very first job, said that even getting the boy to his rehearsals was a struggle.

"They were so poor I had to use my own money to make sure that he got to and from rehearsal," Hopkins told New York magazine in 2001. "Macaulay would crawl under the bleachers at the theater to look for change that had fallen out of people's pockets. They were like the Beverly Hillbillies."

After he shot to fame, Culkin's world came tumbling down when his parents went through a bitter divorce that ended up dragging him and the money he'd made as a child star into it. This was around the time that he had begun to grow tired of acting and started to rebel and live his life out of the spotlight. By 18, he'd gotten married and within a few years, he was divorced. Then he embarked on his nearly decade-long relationship with Kunis. Despite seeming well-matched, the relationship ended terribly.

But in 2017, Culkin met Song in Thailand on the set of the film "Changeland," which was directed by their mutual friend Seth Green. Much like Culkin, Song also started her career as a child actress and is known for her roles on the Disney Channel. She starred in movies and shows such as "Get a Clue," "Wendy Wu: Homecoming Warrior" and "The Suite Life of Zack & Cody."

Of Culkin and Song's blossoming relationship, Green later said he "didn’t see that one coming" when he cast his two friends in "Changeland." And it seems that while Culkin's child star history has plagued him, it's also what brought him and Song together. She told Entertainment Tonight in 2019:

“It’s almost like child actors, we don’t (have) to talk about it. You just look each other in the eye and you nod and we know.” 

But it seems that Culkin had a hard time opening up to love following his previous negative experiences. He told Esquire that he had the feeling their relationship was too good to be true and that he was waiting for the other shoe to drop. He said: “And it’s always gonna drop. Something bad’s gonna happen. Someone’s gonna die!” Thankfully, Culkin gave into the fact that his relationship with Song was a positive one and the two have been incredibly happy ever since.

At the time of Culkin's Esquire interview in 2020, the couple had bought a house together and lived there with a menagerie of animals, including two cats named Apples and Dude, a Shiba Inu named Panda, a fish named Cinnamon and a bird named Macho. Since then, they've added a baby to the mix, after they welcomed a newborn bundle of joy on April 5, 2021, in Los Angeles, California. Their baby boy, Dakota Song Culkin, was born healthy and is named after Culkin's late sister Dakota, who passed away in 2008.

Then in Jan. 2022, a People Magazine exclusive broke the news that the couple was engaged. The magazine reported that Song, 34, was spotted wearing an engagement ring in Beverly Hills earlier that month. Culkin has certainly had his struggles, but it's heartwarming to know he's since found true happiness with Song and their growing family.

Congratulations to Macaulay Culkin and Brenda Song! What do you think of Culkin's journey to finding true love and happiness with Song? Let us know — and be sure to pass this on to those you know so they can read about it too!