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Originally posted by Monster Megamind
Because he gay
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I don't think it's George Michael's sexuality so much as it is his personal and legal problems. Elton John's career lasted for decades after he admitted his bisexuality. Michael's drug usage (which I personally have no problems with) does appear to have hurt his ability to make music. Also, keep in mind his songs and videos are widely available for streaming, whereas Prince's are not. That's also lessening Michael's ITunes imact.
On top of that, Michael hasn't had a hit in the US in 20 years. You could argue the same for Prince, but his 2007 SB halftime show was huge. Prince's legacy in the US was rivaled only by MJ and Madonna. While Michael's Faith was huge here, that was in the late 1980s, and he failed to follow that up with any albums anywhere close to that big. He semi sort of sabatoged his career with his refusal to actively promote his follow up to Faith.
By what I'm reading on ATRL, I'm assuming Michael must've remained relevant in the UK and.WW long after the US stopped listening to and caring as much about his music.