OK, maybe 16: Kylie, Johnny Cash, Justin Timberlake, Cher, Green Day, Cee Lo, more
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Cee Lo Green
By time Cee Lo Green left hip-hop crew Goodie Mob in 1999, the group was just coming off a No. 6 charting on the Billboard 200. But that didn't mean his initial solo outings were popularly embraced. The singer released two albums that tanked before he met his match in Danger Mouse and formed Gnarls Barkley in 2006. And that's when "Crazy" things happened. The duo's second album didn't do as well, so in 2010 Green tried the solo guise again and found himself singing "F*ck You!" and ended up with a runaway hit.
- Katie Hasty