Wayne made his album debut in 1999, with Tha Block Is Hot, which was certified platinum by the Recording Industry Association of America. His later albums, Lights Out released in 2000, and 500 Degreez, released in 2002, attracted minor attention.

Carter's seventh studio album, Rebirth (2010) experimented with rap rock and was released in February of that year to generally negative critical response. A month later in March, he began serving an 8-month jail sentence for criminal possession of a weapon stemming from an incident in July 2007.

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.