Lil Wayne
While some may laugh at Lil Wayne's inclusion on the list, he is deserved. Ignore his childish auto-tuned sing-song rapping on his radio-friendly tunes and you'll discover a talented poet. He's spent decades honing his technique, which now includes multisyllabic rhyming, ingenious rhyme systems, and copious amounts of wordplay.
Together with his other mates from the Young Money label, he popularized, and some would say pioneered, the usage of analogies (rather than similes) in his wordplay, which reads more like a jest with a punchline than almost anything else. His defining characteristic is how he never misses a line. They are jam-packed with these gags that come so quickly that you can't possibly take things all in on a single listen.
Wayne landed a professional job at the tender age of 13, when he was signed to CashMoney Records by Birdman. He then became a member of the Hot Boys, which spawned numerous chart-topping acts, including Juvenile. Lil Wayne has manufactured over 100 million albums, making him the best-selling artist in the world. The rapper is the recipient of five Grammy Awards, eleven BET Awards, and several other honors.
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Years active: 1995 - now
Awards: 143
Hits: Lollipop, Sucker for Pain, Mirror
Website: http://www.thacarterv.com/