Wayne's first post-prison single (which he cut for Tha Carter IV) suggests his teeming brain was eating itself during all that time alone: Rarely has the man sounded so virtuosically loopy. Over thick synth burble and a "Banana Boat Song" sample, he makes up for lost nooky ("Never met the bitch but I fuck her like I missed her") and sprays intense metaphysical graffiti all over: "Life is the bitch and death is the sister/Sleep is the cousin/What a fuckin' family picture."

Gallery: Lil Wayne's Journey

“Baby Got Back”

While watching a Budweiser commercial during the Super Bowl, Sir Mix-a-Lot thought the skinny female models in the ad didn’t represent reality. So he wrote this ode to ample bottoms, featuring its famous to-the-point lyric: “I like big butts and I cannot lie.” MTV banished the video, featuring shaking booties and sexually suggestive fruit, to 9 p.m. or later. “I thought my career was over,” he told Rolling Stone. “Then I called Rick Rubin, and I told him the video was banned, and he was like, 'Great!' We sold another 2 million records.”