Dennis Rodman
The quirky NBA player, who sometimes dressed up as a woman, made $27 million during his career, but in 2012, Rodman allegedly owed $860,376 in spousal and child support and was facing a few counts for contempt of court. In 2014, he went to rehab for alcoholism. Now he’s trying to pull back, working on the show “Halo” which will premiere in 2019.