Michael Jackson
Obviously the first set of child molestation charges caused great damage to his career, but I think he could have overcome these problems.
Because he truly was innocent, (as the boy later revealed he lied), he should have been a lot more confident about the whole thing and not done things to make him look guilty (paying the Chandler family). I'm not sure he should have hidden away either. I think these acts caused damage to his career.
But they didn't ruin his career, because HIStory was still a mega success in 1995. Perhaps one of the biggest mistakes was not releasing a studio album in 1997-1999. This would have been a perfect time to release an album and it would have kept him in the public eye for the right reasons. A remix album wasn't good enough. And by the time he released 'Invincible' in 2001, a lot of people had moved on it seemed and he had become weirder and weirder (not helped by the plastic surgery). So that long break he took between 1995-2001 was definitely career damaging.
By 2001, his career was already a mess, but the Martin Bashir documentary obviously made things worse. It was now confirmed that MJ was quite a strange guy, and this led to all sorts of bad press, meaning MJ became more of a recluse. Downward spiral just got worse and his career just nose-dived from this point. He was still a great catalog seller, but he released no new music, didn't make many public appearance, was in and out of court, behaved erratically and became dependent on drugs, ultimately leading to his death.
So for Michael, I'd say the following things are where it all went wrong:
- 1993 molestation charges and how he handled them publicly
- Not releasing a studio album between 1995-2001
- Martin Bashir documentary