5. Will Smith
Don't think Will Smith ever fell off? Then you don't remember the mid-90's. DJ Jazzy Jeff and The Fresh Prince were still recording even when he was on TV, but people could only handle so much Will Smith. Plus, they were trying to fit into the harder-edged '90s rap construct. As Wikipedia said of their 1992 album, Homebase: "The final single for the release was 'You Saw My Blinker', a song about an old lady that crashed into [Smith]'s new car and his anger at the events that happened thereafter." Yuck, no wonder Will finally cursed in that song! (He said the B-word.)
The next album went gold, and that's when Will decided to concentrate on acting full-time. He came back to rapping after 1996's Independence Day and 1997's "Men In Black," when it was just like, "Oh, right, remember that I could do this, too?" He dropped the trio of "Gettin' Jiggy Wit It," "Miami" and "Just the Two of Us" like they were nothing, staying in the number-one spot for what felt like my entire middle school existence.