Aubrey Graham parlayed a teenage acting career on Degrassi: The Next Generation into a self-released mixtape run that made him hip-hop's defining crossover star of the 2010s, blending confessional, Auto-Tune-streaked singing with punchline-dense rapping until the line between the two nearly disappeared. Signed to Lil Wayne's Young Money in 2009 after the breakout mixtape So Far Gone, he built an empire out of Toronto's OVO sound — moody, R&B-soaked, endlessly adaptable to whatever regional trend (dancehall, UK grime, Southern trap) he absorbed next. He remains the most commercially dominant rapper of his generation, with more Billboard Hot 100 entries than any artist in history.
Drake has called Kanye 'the most influential person, as far as a musician, that I've ever had in my life,' and the connection is nearly literal: his So Far Gone track 'Say What's Real' is built directly over the instrumental from Kanye's 808s & Heartbreak track 'Say You Will,' the album whose Auto-Tuned, melody-first confessional mode set the template for Drake's own singing-rapping hybrid.
listen forPlay Kanye's icy, vocoder-laced 'Say You Will' and then Drake rapping and half-singing over that same beat on 'Say What's Real' — the debt isn't subtext, it's the literal foundation of the track.
Wayne discovered Drake's early work, signed him to Young Money in 2009, and became his direct mentor inside Cash Money — the internal-rhyme density, stream-of-consciousness punchlines, and constant ad-libs on Drake's breakout mixtapes descend straight from Wayne's late-2000s mixtape style.
listen forPlay Wayne's free-associative 'A Milli,' built almost entirely from internal rhyme and left-turn wordplay, next to Drake's 'Headlines' — hear the same instinct for stacking a boast three or four rhymes deep before the beat catches up.
Drake has repeatedly named Aaliyah among his biggest influences, has her portrait tattooed on his back, and in 2012 finished and released her unreleased vocal track 'Enough Said' with producer Noah '40' Shebib — the hushed, close-mic'd, barely-above-a-whisper vocal intimacy she pioneered runs through Drake's own late-night R&B mode.
listen forPlay Aaliyah's breathy, understated 'Rock the Boat' next to Drake's 'Marvins Room' — both trade belting for a murmured, almost overheard-in-private vocal, letting restraint do the emotional work a bigger voice usually would.