1. MC Hammer
Everyone knows this story: MC Hammer danced his way to the top of the charts, made a ton of money and then pissed it all away by attempting to employ half of Oakland while on tour. (Who would've thought that the backlash would come so quickly?) MC Hammer's brand of swishy-Pepsi-rap was no match for the gun-toting hyper-realism that soon assaulted the airwaves, so he had to change his image and sound.
In 1994, his "Pumps N a Bump" video came out, and—while Hammer was more...aggressive—he was wearing a Speedo and thrusting and yuck. Not the best way to win over hardcore fans! He dissed A Tribe Called Quest, Run–D.M.C. and Redman; his more-mainstream followers deserted him. So, he signed to Death Row Records. Once again, it read inauthentic. He wasn't even on the ropes; he was on the floor. He became a punchline for The Simpsons, a sob story on Behind the Music. He only became 'a thing' more recently once Twitter suggested that people follow him, for some indiscernable reason.