Hit singles from the album, "A Milli" and "Got Money," featuring T-Pain hit the Top-Ten. One album track "Mr. Carter," guest lyricist Jay-Z whose last name happens to be Carter as well, anoints Lil Wayne as his successor as the crown holder of rap: "I share mic time with my heir to the hip hop throne Young Carter. Go farther. Go further. Go harder." From this album Lil Wayne won eight 2008 BET Hip Hop Awards, these would include MVP, and four Grammy's, also Rap Album of the Year.

Wayne shocked hip hop heads alike when he announced that his next album, Rebirth, would be a rock album. He began making appearances with a guitar at the Country Music Awards. It was here where he appeared onstage during Kid Rock's performance, strumming on a guitar. Up and rising singles from the album, "Prom Queen" and "On Fire," peaked at Number 15 and Number 33 reletively far lower than Wayne's previous singles. Although originally scheduled for release in April 2009, Rebirth was pushed back several times. His extremely popular take on several of the billboard chart’s top hit was compiled in the mix tape No Ceilings in April of 2009. We all know Lil Wayne never goes longer than six months without releasing new material. No Ceilings popularity grew larger than originally expected. Some would say it even outshined Rebirth, which was finally released on February 2, 2010, just before the rapper was scheduled to report to prison to serve a yearlong sentence on the earlier mentioned gun possession charges.

In February 2010 Lil Wayne landed the cover of Rolling Stone. In the cover story, Lil Wayne told the magazine that though he knew several people from his old neighborhood that has served jail sentences he hasn't asked any of them for advice on how to prepare. "This isn’t something you get advice on," he said. "This is Lil Wayne going to jail. No one I can talk to will tell me what it’s like. Ironically Wayne just says he is looking forward to his time in incarceration.