4. Billy Corgan
For those that came up in the grunge era, Billy Corgan and his band the Smashing Pumpkins were a welcome retreat from the aesthetic of Kurt Cobain and Nirvana. For those that never felt like they fit in with that world, they gravitated to Corgan's shy and introspective reflection, rather than Cobain's screaming, disoriented way of lashing out at the world. Cobain and his followers took their pain and projected it outwards.
Corgan, on the other hand, took it all inside and expressed it as hurt rather than rage. If this sounds emo, it's because the Smashing Pumpkins did fit the emo scene (in its original form) a lot better than they fit the grunge scene which spun off from the meatheaded anger of metal and hardcore.
But we're decades beyond that. Cobain is dead, emotion is music is almost dead, and Corgan, having grown far too old for anyone to buy his pain anymore, has fallen off the horse and into some kind of deranged lunacy. He's become wildly self-indulgent, refusing to let his band die even as he is the sole original member left in it, even as he's burnt bridges with every former member.
He started his own wrestling organization and he's writing an hours long concept album that has been released in spurts for three years and counting, never seeming to get any closer to the finish line. Everything he does is borne of egotism now it seems, but much of it reeks also of pure insanity, desperation, and bitterness at the world.
And ironically enough, he ended up dating Courtney Love.