Now: Macaulay Culkin
Culkin spent the late 1990s the next few years embroiled in a bitter dispute with his father over control of his finances. He was officially "divorced" from his father and manager over his $30 million fortune. Culkin has periodically appeared in films, from 'Party Monster' and also had to testify in the Michael Jackson molestation trial. (Photo by David Livingston/Getty Images)