Lil Wayne's rise from scrappy New Orleanian underdog to one of rap's biggest stars (and easily one of its most talented) has been a slow one. Inducted to the Cash Money family while still a young teen, the MC trained under some of Southern rap's greatest spitters.

In the time since, we've seen him embrace many roles: the hyperactive teenage soldier; the blinging bounce-rap hookmaster; the mixtape assassin; the syrup-sippin' space cadet experimentalist; the Auto-Tuned pop-rap heartthrob; and the wannabe rock star.

From a distance, these creative periods seem disparate, if not completely schizophrenic, but the evolution makes sense when you look at his enormous body of work as a whole. At his best, Weezy is all of these things at once, a jack of all trades and a master of most. As he emerges from his much publicized Riker's Island stay, Complex jumped headfirst into Wayne's seemingly infinite discography to select The 100 Best Lil Wayne Songs...

Listen to Complex's Lil Wayne playlists here: YouTube/Spotify/Rdio

Written by Andrew Noz (@noz)

This story originally appeared in altered form on November 3, 2010.

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