Culkin was ranked No. 2 in VH1 and E!'s respective lists, the "100 Greatest Kid-Stars" and "50 Greatest Child Stars".
Early lifeCulkin was born August 26, 1980 in Manhattan, New York City, and raised in Yorkville, the son of Patricia Brentrup and Kit Culkin, a former stage actor known for his productions on Broadway. Culkin was raised Roman Catholic; he attended a Catholic school (St. Joseph's School of Yorkville) for 5 years before moving on to Professional Children's School. Culkin also studied ballet at the School of American Ballet. Culkin was the third of seven children, five boys and two girls: Shane (born 1976), Dakota (1978–2008), Kieran (born 1982), Quinn (born 1984), Christian (born 1987), and Rory (born 1989). Culkin is the nephew of actress Bonnie Bedelia, his father's sister. During Culkin's early childhood, the family lived in a small apartment; his mother was a telephone operator and his father worked as a sacristan at a local Catholic church.
Culkin began acting at the age of four. Early roles saw him appearing in a stage production of Bach Babies at the New York Philharmonic. He continued appearing in roles on stage, television, and in films throughout the 1980s. Notable parts in this period included an episode of the popular action series The Equalizer in which he played the victim of a kidnapping, and also in the TV movie The Midnight Hour. In 1989 he starred in Uncle Buck with John Candy.
Culkin rose to international fame with his lead role as Kevin McCallister in the blockbuster film Home Alone (1990), where he was reunited with Uncle Buck writer and director John Hughes and Uncle Buck co-star John Candy. He reprised the role of Kevin in the 1992 sequel Home Alone 2: Lost in New York.
Culkin also starred in a Saturday morning cartoon entitled Wish Kid, and hosted Saturday Night Live in late 1991.
Despite the huge success of Uncle Buck, Home Alone, Home Alone 2: Lost in New York, and My Girl, other films Culkin acted in, such as The Good Son, only did reasonably well (although he was nominated for MTV Movie Award in the category for Best Villain for his performance in the film). Getting Even with Dad, Richie Rich, and The Pagemaster, all released in 1994, were only mildly successful at the box office. He also appeared in a filmed version of The Nutcracker as the title role in 1993, which was staged from the 1954 George Balanchine New York City Ballet version of the ballet. He appeared in the 1998 music video for the song "Sunday" by the rock band Sonic Youth.
After several years of inactivity, Culkin returned to acting in 2000 with a role in the play Madame Melville, which was staged in London's West End. In the spring of 2003, he made a guest appearance on the NBC sitcom Will & Grace. His role as Karen Walker's deceptively immature divorce lawyer won him favorable reviews. Culkin headed back into motion pictures in 2003 with Party Monster, in which he played a role very different from those he was known for, that of party promoter Michael Alig, a drug user and murderer. He quickly followed that with a supporting part in Saved!, as a cynical wheelchair-bound, non-Christian student in a conservative Christian high school. Though Saved! only had modest success at the box office, Culkin received positive reviews for his role in the film and its implications for a career as an adult actor.
Culkin began doing voice-over work, with his appearances on Seth Green's Robot Chicken. In 2006, he published an experimental, semi-autobiographical novel, Junior, which featured details into Culkin's stardom and his shaky relationship with his father. Culkin starred in Sex and Breakfast, a dark comedy written and directed by Miles Brandman. Alexis Dziena, Kuno Becker and Eliza Dushku also star in this story of a couple whose therapist recommends group sex to them. Shooting for the film, Culkin's first since Saved!, took place in September 2006. The film opened in Los Angeles on November 30, 2007, and was released on DVD on January 22, 2008 by First Look Pictures. Culkin's next project was a role in the thirteen-episode NBC television series Kings as Andrew Cross.
In 2009, Culkin appeared in a UK-based commercial for Aviva Insurance (formerly Norwich Union) to help promote their company's rebranding. Culkin stared into the camera citing the phrase "Remember me."
On August 17, 2009, Culkin made a brief cameo appearance on WWE Raw at the Scottrade Center in St. Louis, Missouri, following a "falls count anywhere" match between Hornswoggle and Chavo Guerrero in which Guerrero was defeated by the classic Home Alone gag of rigging a swinging paint can to hit him upon opening a door. Culkin appeared in the doorway and said, "That's not funny."
On September 17, 2004, Culkin was arrested in Oklahoma City for the possession of 17.3g of marijuana and two controlled substances, 16.5 mg of Alprazolam and 32 mg of Clonazepam, for which Culkin was briefly jailed but soon released on a $4,000 bond. After being arraigned in court for misdemeanor drug offenses, he pleaded not guilty at the trial (October 15, 2004 to June 9, 2005), then later reversed the plea to guilty. His lawyers reached a plea bargain with the state of Oklahoma and Culkin received three one-year suspended prison terms, forced enrollment into a probationary drug treatment program and a $540 fine.
Friendship with Michael JacksonAround the time of the first Home Alone movie, Culkin became close friends with pop singer Michael Jackson, making an appearance in Jackson's "Black or White" music video. Culkin and Jackson went on vacations together to such places as Bermuda and Disney World, and Culkin often stayed at Jackson's Neverland Ranch home. Culkin's brothers, Shane and Kieran, occasionally joined them. Jackson later asked Culkin to be godfather of his children Michael Joseph "Prince" Jackson Jr. and Paris Michael Katherine Jackson.
During the trial against Michael Jackson, Culkin reported he had slept in Jackson's bed on countless occasions, but that Michael Jackson never sexually molested him or touched him in improper ways, and referred to the allegations as "absolutely ridiculous." Culkin attended Jackson's funeral on September 3, 2009.