49. Chael Sonnen
Hateful lowlight: Pleading guilty to money laundering and getting a reduced sentence for testifying against others in a mortgage fraud scheme.
Chael Sonnen's UFC career has certainly been a weird one. The former University of Oregon All-American wrestler has two Fight of the Night awards, but his career has been marred by strange incidents. He nearly won the Middleweight championship, beating Anderson Silva on points heading into the fifth round. However, Sonnen got trapped in an armbar and tapped out. In 2010, he was suspended for a year for failing a drug test, and in 2011 he pleaded guilty to money laundering involved with his side-job as a real estate agent. Last month, he challenged LeBron James to a fight after Bron Bron allegedly told Sonnen's fiance that her nipples look like "tic tacs." LET'S GET WEIRD.