2011 Ranking: 14

With a co-sign from Lil Wayne, a few important feature credits and his major label debut under his belt, the Jewish-and-black rapper from Toronto, Canada known as Drake was officially promoted to the big leagues with the release of his sophomore album, Take Care. While the revealing tales from childhood and vintage voicemails from grandma demonstrate how rap’s most introspective MC can fixate on the past, his actions show him looking to the future, building his confidence by any means necessary. But Drizzy’s not serious all the time. Ask him about his drink of choice, stance on “practice” before a big game, or if he has any mottos.

Aubrey Drake Graham rose from teen soaps in his native land to touring with Lil Wayne, creating cultural movements with lyrical acronyms and introducing listeners to a more sensitive side of hip-hop.

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Drake’s lyrics exist as a running commentary of the life of a 25-year-old man still figuring out how to be comfortable in his own skin. His videos are more often than not an excuse for famous friends to stand around and look menacing. But Drake brings an evolved sense of security and self-confidence to hip hop even as he creates an incredible party.

“You only live once / That’s the motto, ni–a, YOLO.” Weezy and Drizzy’s “The Motto” took some time to catch fire, but with the song’s momentum, 2012 became the year of living dangerously, with fans and network news anchors embracing “YOLO” with reckless abandon, qualifying every act of gluttony, randomness or stupidity with the guilt-free excuse.

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Drake’s clearly not afraid to take risks. An early listen to Take Care track “Marvin’s Room” pulled back the curtain on him as a singer. No one is more proud of Drake for stepping outside the box than Drake.

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He’ll even go so far as to claim he’s the first person to “successfully” rap and sing on one album. Between that and invitations to the passageway of sexytimes, interviews with Drizzy are rarely boring.

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Drake’s taken lessons from his Young Money boss and applied them to his own practice of developing new artists. He’s been a supporter of fellow Toronto act The Weeknd, collaborating with him on Take Care and welcoming him to his own hometown festival two summers in a row.

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After 631,000 copies sold and a No. 1 spot on the charts, Drake remained a superfan with a crush, letting the world know how he feels about the late singer Aaliyah by commemorating his fandom with ink.

Even if his feelings on fan body art can be hypocrytical.

And then there’s Rihanna. Drake and RiRi have a chemistry that’s undeniable, not to mention a possible romantic entanglement in their past. He recruited her to sing the hook on his album’s title track, and imaginations ran wild.

Suddenly, the tabloids were talking about a love triangle. And because two guys from different circles who may or may not be going after the same girl can’t exist in the same club where glass bottles are served, there was some trouble.

The bar fight that took out a chunk of Breezy’s chin and almost cost San Antonio Spurs’ star Tony Parker his eye was rumored to be about RiRi. Drake has remained quiet on the subject.

As all signs point to a continued if not growing presence on the Top 40, Drake’s expanding arsenal of musical weapons sets him up nicely for the future, whether that entails more voice work, hookah-inspired tracks or producing the album of his dreams.