#6 Evan Rachel Wood and Marilyn Manson
Marilyn Manson had many twisted relationships over the years, yet his affair with Evan Rachel Wood, who was 19 when the two got together, was certainly the most disturbing of all. Back in 2007 Manson was 38, so you can imagine the controversy. The media and all the tabloids wrote many stories about the way Mason was controlling Wood’s life choices and career. Rumor has it that he somehow persuaded Evan to adopt his extravagant make-up style. After a couple of failed engagements the couple finally broke up in 2010.