Macaulay Culkin has been troubled from a young age, making no secret of the fact that his relationship with his parents is strained at best. He has been estranged from his controlling father for years. When a photo surfaced recently of the young actor looking emaciated and unwell, rumors immediately began to fly that he’s on drugs, and the National Enquirer even issued a public plea for him to seek help for an addiction to heroin. Although Culkin’s reps have denied any drug use, those close to him say they’ve witnessed troubling behavior in their friend; some attribute it to a failed relationship with a certain actress, while some say he’s haunted by the family ties he’s severed. And while we all feel like we know the guy we watched grow up, it’s certain that he’s been burned by a life so publicly lived.

Culkin came into most of our lives as the tow-headed revenge-enthusiast Kevin McCallister in the hugely successful “Home Alone” films. Since then, he’s taken several roles completely outside of those we’re used to seeing him in, such as rave kid/drug addict/murderer Michael Alig in “Party Monster”, which was based on true events. While many were shocked to see the boy who once slapped after-shave on his cheeks and screamed as anything other than the lovable John Hughes creation we all came to know and love, some think Culkin was ready to shed that image long before he actually did.

Here are some surprising things you might not know/remember about him.

1. He was married to actress Rachel Miner from 1998 to 2000; they separated and later divorced in 2002.

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Image credit: WireImage

2. He jumped right into a relationship with Mila Kunis the same year; they stayed together until 2011.

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Image credit: WireImage

3. As a kid, before he hit superstardom with “Home Alone”, he appeared in the Tim Robbins Vietnam thriller “Jacob’s Ladder”, then went on to portray a disturbed and murderous young boy in “The Good Son”, opposite Elijah Wood.

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Image credit: Tri Star Pictures

4. He was close friends with Michael Jackson and slept over at his house several times; he later testified that nothing inappropriate ever happened while he was there and he never witnessed Jackson touching the other children who stayed there.

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Image credit: Zimbio.com

5. He starred in his own animated series in the early 90’s.