What artists managed to become "uncool" again after being "redeemed"?

I was thinking lately this is the trajectory of Justin Timberlake. At the start of his career he was very hated just for being the most visible member of N Sync, a Lou Pearlman manufactured boy band, which was like the absolute bottom of the hipness totem pole in that day. But then his solo career actually gained some respect and most notably his acting career, for awhile he was actually regarded as a sort of "it" actor that would have appeal to the hipster crowd like Joseph Gordon-Levitt or Zooey Deschanel around the same time period. But then Man of the Woods caused him to drop off again, the DUI arrest got him mocked and his reaction was a terrible look, and his acting career has totally fallen off, I can't think of any notable acclaimed films he's been in since perhaps Inside Llewyn Davis which was over a decade ago. Now he's just a mocked celebrity punching bag and completely uncool again.