Originally known as the youngest Hot Boy, Lil' Wayne has orchestrated a steady stream of hits. The New Orleans rapper began his long career with Cash Money as part of the Hot Boys, a popular late-'90s supergroup consisting of Juvenile, Turk, and B.G.

3 Peat
Mr. Carter [Feat. Jay-Z]
A Milli
Got Money [Feat. T-Pain]
Comfortable [Feat. Babyface]
Dr. Carter
Phone Home
Tie My Hands [Feat. Robin Thicke]