With “Lollipop,” Wayne crafted one of the biggest crossover singles ever, establishing the complete hip-hop domination he'd been talking about for years. If there were still any doubters, “A Milli” proved not only that he could play in the pop lane, but that he could out-rap just about anyone.

He has influenced countless artists with his unique style, which combines intricate wordplay, clever metaphors, and a distinctive voice. Lil Wayne is also known for his ability to freestyle, which has earned him a reputation as one of the best rappers of all time.