Boy George
Culture Club singer Boy George was involved in a strange sex scandal that ultimately tarnished his reputation. He served 15 months in jail for handcuffing and beating a male escort in his hotel room. Doesn't matter how catchy "Karma Chameleon" is, this guy is definitely unwell.
A Reality Judge
Like many singers whose careers have lost relevancy, George has been a judge on various iterations of The Voice. He's also made several attempts at reviving his solo career, but the songs flopped for the most part. He's also used his platform to chair several cancer-related initiatives.