In February 2006, Drake released his first mixtape Room for Improvement. It was made available via his website and official MySpace page. From the success of his first mixtape, he later began releasing more, capitalizing from the buzz.

In 2007, he released Comeback Season to much critical acclaim and praise. Which produced a single and a music video for Replacement Girl featuring Trey Songz. It also contained a freestyle over a song with Lil Wayne, a remix of the already popular song "Man of the Year" originally by Brisco and Flo-Rida. Also in 2007, Drake became the first unsigned Canadian rapper to have his music video featured on BET when his first single, "Replacement Girl" was featured as the "New Joint of the Day" on April 30, 2007.[13] On Febuary 13, 2009, Drake released his third official mixtape, So Far Gone, for free download on his blog site which included Drake's mentor Lil Wayne, Bun B, Omarion, Lloyd and more. Due to the success of the mixtape's two singles, "Best I Ever Had" and "Successful", it was released as an EP featuring only five songs from the mixtape and one new song.

Since So Far Gone, Drake worked with Jay-Z, Kanye West, Young Jeezy, Mary J. Blige, and Jamie Foxx. Drake has also written for Jazz Cartier, Bishop Brigante, and Dr. Dre.