Robin Thicke
2013's "Blurred Lines" will likely always live in infamy. Not only was the video incredibly raunchy, but his one-time performance with Miley Cyrus was just as uncomfortable to watch. There was a certain R-rated dance move performed, and Thicke tried to blame it on Cyrus. That didn't work, Thicke's wife filed for divorce, and his career tanked.