He achieved massive success starring as "Kevin" in the two Home Alone (1990, 1992) movies, capturing the minds of many young movie-goers as he outsmarted two bungling burglars with clever homemade traps. He had less success with the more serious The Good Son (1993), but other children's films such as The Pagemaster and Richie Rich kept him a popular mainstream child actor.

Culkin's father was his manager in the early years of his acting career. Macaulay stopped making movies at the age of 14, when his parents separated and went to court over the control of their business and the custody of the kids. The court case went on for several years and ended in April 1997, when his father decided to withdraw from the case. He has claimed numerous times that his father, Christopher "Kit" Culkin, was abusive. Culkin has had no contact with his father since 1996, except for a telegram in which his father congratulated him on the continuation of his acting career. Culkin enjoys theatre and made a well-heralded return to theatre in the 2000/2001 season, when he starred opposite Irène Jacob in Madame Melville.

Culkin is a close friend of Michael Jackson and godfather of Jackson's first son and daughter. Jackson and Culkin can be seen in a home video compilation Jackson released (Michael Jackson's Private Home Movies); they are shown playing and going on holidays together when Culkin was 10 and 11 years of age (they cruised the Caribbean in 1991). Jackson also claimed that Culkin and his siblings slept in the same bed with Jackson. Culkin said at the age of twenty, "We talk all the time. I think we understand each other in a way that most people can't understand either of us."

Macaulay Culkin is the most famous and successful of his six siblings: Quinn, Kieran, Christian, Shane, Rory, and Dakota. Other than Dakota, all of Macaulay's siblings have acting credits; Kieran is most famous for starring in Igby Goes Down, while Rory is famous for starring in M. Night Shyamalan's Signs.

Culkin is one of many notable graduates of Professional Children's School in New York City.He married Broadway actress Rachel Miner in 1998, when both were 17; they split up in 2000.

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