[5] Culkin's early career involved working on Broadway in theater productions with actors such as Richard Burton, John Gielgud, Laurence Olivier and Anthony Quinn.

[citation needed] Three of his sons — Macaulay, Rory, and Kieran — are professional actors whose careers he managed from the late 1980s to the mid-1990s.

Macaulay became popular due to his starring roles in the Home Alone films, and he was the first child in Hollywood to receive a million-dollar salary (for My Girl in 1991).

His other children, Shane, Dakota, Macaulay, Kieran, Quinn, Christian, and Rory, were with Patricia Brentrup.

After his long-time friend and partner Jeanette Krylowski died, on May 31, 2017, Culkin left his Grants Pass residence.