Macaulay Culkin was one of the most famous child actors of the 90s, starring in a series of blockbuster films that earned him A-list status almost overnight. However, after reaching his teenage years, Culkin began to suffer from legal disputes with his parents largely caused by the control of the money he had earned from his work. He was later arrested for drug possession, and he also lived through a scandal where a controversial friendship with Michael Jackson, in which it is said the "King of Pop" would have sexually abused him as a child and later, having married at age 17. After stepping away from the spotlight, Culkin began moving through life as any young adult would, which included pursuing romantic relationships. He married actress Rachel Minor in 1998—when they were both just 18 years old—but the couple split two years later and officially divorced in 2002. In April of 2021, he welcomed his son Dakota with his girlfriend Brenda Song, and the couple announced their engagement in January 2022.

Culkin recently returned to the acting circuit in the tenth season of American Horror Story: Double Feature in 2021 and the second season of The Righteous Gemstones the following year. Both roles were critically praised, so there may be hope yet that the former child actor will finally make a full comeback. He also made a runway appearance in 2021 for Gucci.