He had a rather unusual upbringing as a budding young actor in Hollywood, always somewhat in the shadow of his then-mega child star older brother Macaulay Culkin.
But now, after hitting his stride as the scene-stealing Roman Roy in HBO's huge hit Succession, Kieran Culkin is getting candid about how he is finally ready to embrace his acting career at age 39 - after 30 years in showbusiness.
The actor got personal in a rare interview with The Hollywood Reporter and also spoke about the impact the death of his sister Dakota had on him, who was killed in a car accident at the age of 29 in 2008.
'That's the worst thing that's ever happened, and there's no sugar coating that one,' Kieran says when asked about the tragic passing of his sister, was struck by a car when she stepped off the curb and in front of a moving vehicle.
Candid: Kieran Culkin opens up to The Hollywood Reporter
'I still weep about it': Succession star Kieran Culkin talks losing his sister Dakota who died aged 29 in a car accident
'Each one of us handled it very differently. I think everyone was just torn up inside. What has it been, 13 years now? Holy shit. That's crazy. Jesus f***ing Christ. I accepted at the time that this is going to be forever and it's never going to be fine.'
He continued: 'It's always going to be devastating. I still weep about it out of nowhere. Something funny she did will pop in the head and make me laugh and then I’m weeping.'
'Sometimes it's knowing that she's not going to meet my kids and they don't get to have her and it's hard to describe what she was like.'
Tragedy: Dakota is pictured far right with her family, parents Pat and Kit, and siblings Macaulay, Kieran, Christian, Shane and Gwen
Child stars: Kieran had often lived in the shadow of his mega-famous older brother Macaulay Culkin but is now one of the the breakout stars of Succession
Kieran has been