Rewinding the Charts: In 2009, Drake Began With His 'Best' and Got Better

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Drake with the Toronto Raptors mascot at Toronto’s Air Canada Centre in 2010.

The actor-turned-rapper's third mixtape yielded his first charting single and the beginning of a record-breaking career.

DRAKE'S PLANS TO PIVOT from acting to rapping in the early 2000s weren't exactly received with enthusiasm. In 2009, he told Vibe magazine that the reaction he often got when he revealed his hip-hop aspirations was, "That's really going to be your thing?"

The skeptics were proved wrong when the bouncy, flirtatious "Best I Ever Had," the lead single from Drake's first EP, shot to No. 1 on Billboard's Hot R&B/Hip-Hop Songs chart on June 27, 2009.

The Toronto native — born Aubrey Drake Graham — was 22 at the time and in his eighth and last year playing "Wheelchair" Jimmy Brooks, a teenage basketball star rendered paraplegic after a classmate shot him, in the Canadian TV series Degrassi: The Next Generation.

Drake had planted the seeds for a music career in the midst of his Degrassi fame, releasing three buzzed-about mixtapes: Room for Improvement in 2006, Comeback Season the following year and in 2009, So Far Gone, which contained "Best" and was co-signed by Lil Wayne, who appeared on multiple tracks.

So Far Gone sparked a bidding war for Drake, who ultimately signed with Young Money Entertainment. The mixtape was repackaged as an EP and shot to No. 6 on the Billboard 200.

Since "Best," Drake has only gotten better. He has scored 16 No. 1s on the Hot R&B/Hip-Hop Songs chart (the fourth-most of all time), earned seven No. 1 albums on the Billboard 200 and set a single-night record when he took home 13 Billboard Music Awards in May. In the eight years since his chart debut, Drake has racked up 155 Billboard Hot 100 hits, the most of any soloist, and has had a song on the chart every week since "Best" first landed on May 23, 2009 — an unprecedented 425 straight weeks and counting.