When Home Alone released in November 1990, Culkin was barely 10 years old. Produced for $18 million, the film earned over $476 million at the box office and made its young star a household name. Culkin hosted Saturday Night Live, and even made a cameo in Michael Jackson’s 1991 “Black or White” music video. By 1994, however, Culkin’s movie career slowed down. In fact, he didn’t appear in a feature film for nearly a decade. Meanwhile, the younger Culkin brothers built up strong acting resumes. So, what has Macaulay Culkin appeared in since Home Alone?
In 1991, Culkin starred opposite Anna Chlumsky in the dramedy My Girl. The film became a box office hit, and further showcased Culkin’s skill set. The following year, he starred in Home Alone 2: Lost in New York, which nearly matched the box office success of Home Alone. Culkin then landed another hit with The Good Son (1993), a psychological thriller. But he then starred in four consecutive flops: The Nutcracker (1993), Getting Even with Dad (1994), The Pagemaster (1994), and Richie Rich (1994). Suddenly, Culkin was no longer a viable Hollywood lead. He also reportedly wanted to live “a normal life.” In 1998, Culkin married fellow actress Rachel Miner.
Culkin returned to feature films with the 2003 biographical drama Party Monster, in which he portrayed former New York City party promoter Michael Alig. In 2004, Culkin co-starred with Jena Malone and Mandy Moore in the progressive comedy Saved! In the years since, he’s only appeared in a handful of low-budget feature films, perhaps to focus on more on his personal life and passion projects. Culkin dated actress Mila Kunis from 2002 to 2010, and later formed a musical project called The Pizza Underground, a comedy rock band that parodied The Velvet Underground songs. Naturally, the premise translated to Twitter culture. In addition, Culkin inspired internet memes during this time period via his meta t-shirt bromance with actor Ryan Gosling and had a few guest spots on Red Letter Media's YouTube show.
In recent years, Culkin has continued to pursue unique projects. He launched the lifestyle website Bunny Ears, and has made numerous appearance on the RedLetterMedia web series Best of the Worst. He even portrayed Home Alone’s Kevin McCallister in a Google ad, marking his first character reprisal in nearly three decades. In 2019, Culkin starred in Seth Green’s Changeland, his first movie role in four years. He’s currently dating his co-star Brenda Song (Secret Obsession).