Growing up in a one-bedroom apartment with six siblings, Culkin faced financial struggles. Despite this, his family's push for acting shaped his early career.

At just 15, Culkin became legally emancipated from his parents. This bold move was a response to the controlling nature of his father and the pressures of fame.

Culkin was close friends with Michael Jackson. Their bond was rooted in shared experiences of childhood fame and trust, with Culkin defending Jackson during legal troubles.

Beyond acting, Culkin co-founded the Pizza Underground, a comedy rock band that parodied songs about pizza. This venture showcased his creativity and humor.

Culkin's romantic history includes marriages and long-term relationships. He is currently engaged to actress Brenda Song, with whom he shares a son born in 2021.