Somewhere between the Carter II and Carter III, Lil Wayne became totally bored of being the best rapper alive and decided, "Fuck it, I might as well be the best R&B singer alive too." (If only if he'd stopped there instead of trying to be the best rocker alive!) As you probably already know, this song is dedicated to Karrine "Superhead" Steffans. So you know her head game must be insane because everyone knows shorty is trife but he still ended up sleeping with her and then making a song about how great she was. Anyhow, we're glad Wayne eventually came to his senses (or down from his high) and stopped trying to make the "BESTSELLING AUTHOR" into a housewife.
#15. Lil Wayne - Prostitute Flange (2007)