12 – Macaulay Culkin
“Merry Christmas, ya filthy animal.” Ranked second on VH1’s 100 Greatest Kid Stars of All Time only behind Shirley Temple, Macaulay Culkin flexed his acting muscle when he was nine years old opposite John Candy in the 1989 film Uncle Buck.
From there, he became the go-to child actor of the 1990s and was cast in hits like My Girl, The Good Son, Richie Rich and fan favorites like Home Alone and Home Alone 2: Lost in New York.
By 2004, Culkin’s childhood appeal had long worn off as the then 24-year-old star had gone years without landing a leading role in a hit film. The same year, however, he finally made headlines only this time at the expense of his stardom.
Picked up by Oklahoma City police with marijuana, Alprazolam and Clonazepam, Culkin was charged with misdemeanors and pled guilty receiving three one-year suspended prison sentences and over $6,000 in fines. While he seems to be clean these days with his most recent television appearance in 2015 on The Jim Gaffigan Show, this former Hollywood golden boy still remains a mystery.