Five years ago today, Drake released So Far Gone, a tape that transformed him from an actor with promise into a fully-fledged hip-hop star. Sure, he already had the connections, the cosigns, the fame, and a hefty early catalog. But as much as these things worked for him, hip-hop is all about underdog stories, and that he didn't have. Ironically, this ended up becoming its own "underdog story," as the artist whose life had little trace of a Horatio Alger tale ended up using that very fact as his obstacle to overcome.

And So Far Gone was when he went from the guy anyone could dismiss to a guy you couldn't—even though many would continue to try. With a twin pair of hit singles (the Trey Songz-assised "Successful" and the smash "Best I Ever Had," which reached No. 2 on the pop charts), he proved that he was no flash-in-the-pan. The tape also first established a consistent sound, a place where to enter Drake's world, you have to breathe his and 40's oxygen—a foggy, atmospheric sensibility that embraced minimalism and ambiguity, in an era when DJ Khaled and Rick Ross were continually amping up the grandeur. While they made the largest of motions, Drake made emotions his focus, zooming in on the tics and particularities of speech that seemed to capture the language of the text and tweet generation.

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Foster Kamer (@weareyourfek), Senior Editor: Five years ago I was, like, the most typical single mid-twentysomething ever after finally embracing being out of a relationship and being single in New York City. In the worst way possible. So obviously So Far Gone spoke to me on that "level." I still laugh every other time I hear anyone talk about the city of Houston outside the context of rap. And the line on "Say What's Real" about the Blackberry still ranks, for me, among the best Drake lines of all time. Revisiting the mixtape isn't a regular occurrence for me, but it's always mostly fun and not too wistful. But it also is a really helpful reminder of why I really, really love Drake's music whenever there's a moment where I'm having trouble doing so (the entire release cycle of Thank Me Later, the beginning of the Nothing Was The Same release cycle, whenever I'm surrounded by millennials who quote Drake like he's Aristotle, etc).

Claire Lobenfeld (@clairevlo), Music News Editor: It wasn't until the summer of 2009 that So Far Gone really hit me. I was 23 and unemployed, spending my days O.D.-ing on Jimmy Brooks-era Degrassi, so Drake was already a credible celebrity in my eyes. His legitimacy was only amplified in the middle of July's thick heat, you'd hear three different Drake tracks from three different cars every other block in Brooklyn, even though it's Jay's and Big's city to soundtrack eternally. Since then, Drake and I have grown in two different emotional directions—nothing was the same, for real. But at the time, when Kanye West, who released The College Dropout at the same time I left school, felt a little too lovelorn and mature for me on 808s and Heartbreak, Drake stepped in. We pined for success together, he stood beside me on the walk of shame, he foretold every awkward party when you're young, dumb, and see your ex talking with your next talking with the one that you're with right now. Drake is always explicating your deepest inner bullshit and that's what makes it work.

David Drake (@somanyshrimp), Staff Writer: I was not a Drake fan then. I still wouldn't consider myself much of a Drake fan now. But you get worn down with time. (Trying to resist something that becomes so stratospherically popular is fruitless, if you're a rap fan, because nothing turns out like you expect, and tomorrow's stars come from today's, whether you want them to or not. I resisted Rick Ross and post Carter II-Wayne, too. Now I'm a fan of both, and they're a part of the furniture.)

But back then? His success felt like he was taking shortcuts, bypassing a lot of what I liked about rap music. Don't get me wrong, this wasn't about his love for R&B or being "soft." I'm a big fan of songs "for the ladies"—R&B joints, "sellout" tracks, the records unafraid of reaching for the pop chart jugular. But to me, Drake's version felt anodyne, defanged, propelled by cynical pandering. (The exception was "Successful," but that was more like a Trey Songz track anyway, and fit in better on Trey's Anticipation.) Drake seemed like a guy who, a few years earlier, would call himself "metrosexual," just so no one would get the wrong idea. And his method of talking about women—being the player with the guilty conscience, rather than just embodying the archetype—seemed to me like impotent handwringing, a way to have your cake and eat it too.

"Best I Ever Had" was a catchy-ass song, though.

Alex Gardner (@TheConstant_G), Staff Writer, Pigeons and Planes: Living in the UK in 2009, Drake's So Far Gone took a little bit more time to gain traction and exposure than in the US, but once it did, it was inescapable. Songs like "Successful" and "Best I Ever Had" were played on mainstream, daytime radio shows, which was probably a first for music from a rap mixtape. In retrospect, So Far Gone was the perfect move for Drake. It had enough rapping on it to ensure that he wasn't dismissed by rap fans, enough catchy hooks to ensure consistent radio play, and enough random indie samples (Lykke Li, Santigold, Peter, Bjorn & John) to appeal to a wider audience. Drake wasn't (and still isn't) the best rapper or the best singer or the best storyteller, but he combines what he does have into a package that connects with such a wide variety of people that we shouldn't really be surprised that he's as big as he is now.

Oh, and for all I fronted like I was jamming to Only Built 4 Cuban Linx II, if you stood outside my window in summer of 2009, you might have heard me singing the chorus of "Best I Ever Had" very loud and very out of tune.

Rob Kenner (@boomshots), Senior Editor: "Best I Ever Had" was the sureshot pop radio smash off So Far Gone. When the tape first came out I used to play that song so much the people next to my office at VIBE would complain. "Is Drake paying your rent or something?" But over time the song that meant the most was "Successful." Trey and Drake sounded great together on that track  (Whatever happened between Drizzy and Trigga Trey? They oughta try and patch it up, cause those two could still make some great music together.) Moreover, the song's aspirational inspiration came right on time for a guy like me who was grinding hard through the late aughts rap media meltdown. Like all rising stars, Drake was more appealing when he was striving for success. He seems thinner-skinned now, but back then you had to root for the kid who knew it was coming, and just hoped he'd be alive for it. As for that "dis me and you'll never hear a reply for it" policy—that was pretty fly too. He might want to revisit that.

Jacob Moore (@PigsAndPlans), Editor-in-Chief, Pigeons and Planes: I grew up listening to a lot of Atmosphere, so it's fair to say that I'm a pretty sensitive guy. I always loved hip-hop, but for a while in the mid-2000s, I felt detached from a lot of the mainstream shit. It felt like a lot of fluff and a lot of people saying the same things in different ways, fronting to convey an image they wanted. "Keeping it real" started to lose meaning. When Drake came along with So Far Gone, it immediately felt like something new was happening. This clearly wasn't "underground" hip-hop, but Drake was saying things that the rappers I was hearing on the radio (besides Kanye) would never say. The first line that really sunk in with me was from "Say What's Real" (appropriately over a Kanye beat), when Drake says, "Don't ever forget the moment you began to doubt / Transitioning from fitting in to standing out." That was a big "oh shit" moment for me, and I've been a Drake fan ever since.

Ross Scarano (@RossScarano), Deputy Editor: The first song I heard was "Bria's Interlude." I was living in Texas at the time, recently graduated from college, and my brother flew in to visit. Once he began playing new music for me, it felt like he'd flown in with the express purpose of introducing "Bria's Interlude," still the track I listen to the most from So Far Gone. That's no disrespect to the rest of the mixtape, which I think is great, it's just that "Bria's Interlude," with its slow Ginuwine/Missy Elliott sample and long-ways-off vocals, is two minutes and 19 seconds of how I want to feel all of the time.

When I started digging into the lyrics and the mood, it was like falling in love with rap again. He was complicated the generally accepted ideas of masculinity in the music I'd been listening to since my mom first took my copy of Busta Rhyme's Extinction Level Event. Even though he's been outpaced in the race to dissassemble the hard vs. soft conversation, he still laid important groundwork. And it all starts with this tape.

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