Culkin began acting at age four. His early roles included a stage production of Bach Babies at the New York Philharmonic. He continued appearing in roles on stage, television and films throughout the 1980s. He made an appearance in the TV movie The Midnight Hour (1985). In 1988, he appeared in an episode of the popular action television series The Equalizer, in which he played a kidnapping victim, Paul Gephardt.

Culkin made his film debut as Cy Blue Black in the drama Rocket Gibraltar (1988). He played the role of Billy Livingstone in the romantic comedy film See You in the Morning (1989), starring Jeff Bridges, Alice Krige, Farrah Fawcett and Drew Barrymore. He starred as Miles Russell alongside actor John Candy in the comedy film Uncle Buck (1989).
Culkin rose to fame with his lead role of Kevin McCallister in the blockbuster comedy film Home Alone (1990). The film reunited him with Uncle Buck writer and director John Hughes and Uncle Buck co-star John Candy, who played the role of Polka band member Gus Polinski. For his performance, Culkin was nominated for a Golden Globe Award and won an American Comedy Award and a Young Artist Award. In a 2022 interview with People, co-star Joe Pesci said Culkin was "a really sweet kid and, even at his age, very professional".

In 1991, Culkin starred in an animated Saturday morning cartoon television series titled Wish Kid, hosted Saturday Night Live and starred in Michael Jackson's "Black or White" music video. He starred as Thomas J. Sennett in the film My Girl (1991), for which he was nominated for Best On-Screen Duo and won Best Kiss at the MTV Movie Awards, with Anna Chlumsky.

Culkin was paid $4.5 million (compared to $110,000 for the original) for Home Alone 2: Lost in New York (1992). He played the role of Henry in the drama thriller film The Good Son (1993), which only did reasonably well, although he was nominated for an MTV Movie Award in the category for Best Villain for his performance. He was also a student at the School of American Ballet and appeared in a filmed version of The Nutcracker as the title role in 1993, which was staged by Peter Martins from the 1954 George Balanchine New York City Ballet version of the work. In 1994, Culkin appeared in three films: Getting Even with Dad (1994), The Pagemaster (1994) and Richie Rich (1994).

Culkin established himself as one of the most successful child actors of the 1990s. He grew tired of acting and retired after Richie Rich. Wanting a "normal life", he went to a private high school in Manhattan. In 1998, he appeared in the music video for the song "Sunday" by the rock band Sonic Youth.
In 2000, Culkin returned to acting with a role in the play Mada…

Read more on Wikipedia

Culkin tends to refrain from disclosing aspects of his personal life; however, he has discussed his life as a child actor, the conflict in his family life, including his estrangement from his father, and how he retired from acting at age 14. He resides in the Toluca Lake neighborhood of Los Angeles on an estate that was formerly owned by Kiefer Sutherland.

On September 17, 2004, Culkin was arrested in Oklahoma City for the possession of 17.3 grams (0.61 oz) of marijuana and two controlled substances, 16.5 milligrams (0.25 grains) of alprazolam and 32 milligrams (0.5 grains) of clonazepam, for which he was briefly jailed and then released on $4,000 bail. After being arraigned in court for misdemeanor drug offenses, he pleaded not guilty at the trial (October 15, 2004, to June 9, 2005), but later reversed the plea to guilty. He received three one-year suspended prison sentences and was ordered to pay $540 in fees.

In December 2018, Culkin announced that he would legally change his name to "Macaulay Macaulay Culkin Culkin" after holding a vote through his website to choose a new middle name, with "Macaulay Culkin" winning the vote over four other candidates. He announced in April 2019 that the legal name change process had been completed.

In August 2020, on his 40th birthday, Culkin tweeted, "Hey guys, wanna feel old? I'm 40. You're welcome." The tweet became one of the most-liked tweets of all time, peaking at number 9.
Culkin married actress Rachel Miner in 1998 when they were both 18, but they separated in 2000 and divorced in 2002.

Culkin began dating actress Mila Kunis in May 2002. By 2006, he was living in New York, while Kunis was living in Los Angeles. On January 3, 2011, Kunis's publicist confirmed reports that Culkin and Kunis had ended their relationship several months previously, saying, "The split was amicable, and they remain close friends."

In 2017, Culkin's Changeland co-star Brenda Song shared that the two of them were in a relationship, having met in June 2017 when they worked together on that film, and after having been seen in public dating the following month. Their first child, a son, was born on April 5, 2021. Shortly after their son's birth, comments Culkin made on a 2018 episode of The Joe Rogan Experience about his relationship with Song (a Hmong–Thai American) resurfaced, which were criticized for stereotyping Asians. In the interview, Culkin joked about the shape of Song's eyes, their interracial relationship, and the appearance of their potential future children. He argued that he was entitled to make Asian jokes because of his relationship with Song, and because of his future fatherhood to multiracial children, stating that he would "understand the struggle". Culkin and Song's second son was born in December 2022.
Around the time of the first Home Alone movie, Culkin became friends with the pop singer Michael Jackson and appeared in Jackson's 1991 "Black or White" music video. In 2005, at Jackson's trial for sexual child abuse, Culkin testified that he had slept in bed with Jackson but that he was never molested. Culkin dismissed the allegations against Jackson as "absolutely ridiculous". Culkin at…

Read more on Wikipedia

• Holmstrom, John. The Moving Picture Boy: An International Encyclopaedia from 1895 to 1995, Norwich, Michael Russell, 1996, p. 398.