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He released two further independent projects, Comeback Season and So Far Gone, before signing to Lil Wayne's Young Money Entertainment in June 2009.which debuted at number one on the US Billboard 200 and was soon certified platinum by the Recording Industry Association of America (RIAA).
In 2007, he released his second mixtape, Comeback Season.
The song also saw Drake sample "Man of the Year" by Brisco, Flo Rida and Lil Wayne, retaining Lil Wayne's verse, and adjoined his own to the song's earlier half.
This caused Jas Prince to gift Lil Wayne the song, which prompted the rapper to invite Drake to Houston in order to join his Tha Carter III tour.
This was later confirmed following a planned lawsuit from Young Money, in conjunction with Drake, against an unauthorized album entitled The Girls Love Drake, which was released on i Tunes under dubious means.
Drake then joined the rest of the label's roster the America's Most Wanted Tour in July 2009.