Macaulay Culkin: Age 14
Macaulay Culkin divorced his father/manager when he was 14 while his parents were caught up in a custody battle over the child star, his siblings, and his Home Alone earnings. His younger brother Kieran later followed suit.
“I did 14 movies in six years [...], and I was just at this point where I really wanted to take a break,” he told Larry King in a 2004 interview. “When I was put in a position where I could take control of my own life and my own destiny and make decisions that were solely for my benefit and not for anyone else to make money on or anything like that, I did. I jumped in there and I said, ‘I’m retired.’”