His second album, Take Care, was released in November 2011 and ultimately led to celebration with his crew for earning his first Grammy Award (for Best Rap Album). The next year, he released his debut album Thank Me Later. During this period, Drake also made a slew of guest appearances on tracks by artists from DJ Khaled to JAY-Z.Īfter years without a record deal, Drake finally signed to Lil Wayne’s Young Money Entertainment label in 2009. These mixtapes got him the attention of Lil Wayne, and spawned the hit singles “Forever” and “Best I Ever Had,” the latter coming from his critically acclaimed mixtape So Far Gone. Drizzy put out three mixtapes from 2006 to 2009: Room for Improvement, Comeback Season, and So Far Gone. Drake is part of a generation of rappers, along with Wiz Khalifa, Kid Cudi and others, who came up through internet mixtapes.