On February 13, 2009, Drake released his third mixtape, So Far Gone, under his then-unofficial October’s Very Own label.

A lot has happened since then. Aubrey “Drake” Graham is now a Grammy award-winning artist that boasts three studio albums. October’s Very Own, founded by Drake and Noah “40” Shebib, became an official label in 2012 through a partnership deal with Warner Bros. Records. He popularized an acronym, “YOLO.” He’s even dived into a few bowls of rap beef (just ask Common, Pusha T and Kendrick Lamar).

Even though So Far Gone was Drake’s third mixtape, it was technically the project that ignited the Canadian rapper’s career. The project, which became an EP later that year, gave listeners a dose of rap-cooing, soft drums and some good ol’ heart-to-heart lyrics. Besides the familiar Hip Hop faces that were featured (Lil Wayne, Bun B), the combination of “soft” content and vocal features (Peter Bjorn, Santigold, Lykke Li) was uncommon at the time. His first single, “Best I Ever Had,” produced by fellow Canadian Boi-1da, was sonically a radio hit and the ladies loved it, obviously because it was drenched in Axe body spray. Girls everywhere (I’m looking at you) were swooning over the feel-good sound and message. “Sweat pants, hair tied, chillin’ with no make-up on / That’s when you’re the prettiest, I hope that you don’t take it wrong.” Wrong? Oh no. We believe you, Drake.

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Five years later, Drake is still spreading the same message even though at times, he’s on his “Worst Behavior.” The rap, singing and production have progressively grown together. Five years ago, Drake found his lane and five years later, he continues feeding fans with the content that drew them in in the first place.