Why Drake’s ‘Comeback Season’ Was His True Star-Making Moment And Most Influential Mixtape


Run It Back is a retrospective review of classic or game-changing hip-hop releases whose style and sound still resonate with listeners in the modern, streaming-driven era. Hip-hop has always been a forward-facing, youth-oriented culture, but it’s also deeply informed by the past. This is our way of bridging the gap, paying homage to rap’s roots while exploring how they still hold relevance today.

In the video for “I’m Upset,” the second single from Drake’s upcoming fifth studio album, Scorpion, he nostalgically returns to his entertainment roots, commandeering the exterior of Studio C of Epitome Pictures and once again dressing it as the facade of Degrassi Community School for a reunion of his castmates and friends from the teen drama Degrassi: The Next Generation.

It’s almost hard to believe that it’s been ten years since the actor Aubrey Graham walked off that set to pursue his dream of rap stardom and simply amazing that not only was he able to achieve it, he has become one of the top names in hip-hop, with multiple No. 1 singles and albums, corporate endorsements, and successful tours under his belt. Once a member of an ensemble cast on a cable TV, high school soap opera, he’s become one of the most recognizable faces in the world.

While much praise is (rightfully) heaped onto Drake’s “breakout” mixtape So Far Gone, it was really first mixtape released after he left his regular role on Degrassi that truly showed off his chops and proved his dream was not only feasible — it was practically inevitable. Released in 2007, Comeback Season may not have had the best title for the mixtape that basically introduced the world to the actor-turned-rapper who would turn the 6 (and the rap world as a whole) upside down, but the music on it embodied the star quality that would come to be his number one calling card, even before he had ever crafted a legitimate hit.

While the video for the album’s first single, “Replacement Girl,” did become the first music video from a Canadian artist to be featured on BET, its reception was lukewarm, to say the least. But the rest of the album showed flashes of the potential that Drake possessed even then, gave glimpses into his multifaceted stylistic approach to hip-hop and R&B, and delved into the varied influences that contained the seeds of his later success.

The most obvious example, of course, is the 23-track mixtape’s centerpiece, “B*tch Is Crazy.” It’s the first sampling of Drake singing on a record, a sort of harbinger for things to come. It’s about — as usual for the man who calls himself “Heartbreak Drake” — a woman with whom his relationship has become fraught. It showcases his gift for melody, for damnably catchy hook writing, and for being so uncomfortably relatable. You find yourself, against your will, comparing Drake’s example of the titular woman’s behavior to your own experience, singing along even though you know that, deep down, Drake has to be at least as much at fault as his lyrical scapegoat — and yet, the hooky chorus snares your ear and won’t let go.

The recurring motif of women, both “good” and frustrating, is a hallmark of Drake’s music, running throughout his catalog like the black thread in an OVO owl sweater. “Replacement Girl,” “Don’t You Have A Man,” and “Think Good Thoughts” all return to Drake’s favorite subject, all approached from a slightly different angle, making him alternately the lovelorn dumpee searching for a rebound, the careworn, but not entirely regretful side guy, and the “good dude” who just deserves a chance, despite his reputation as a player. All of these motifs play into his more recent material, even up to his newer songs like “I’m Upset,” which could very well be a “B*tch Is Crazy” redux, “Passionfruit” and “Hotline Bling,” which illustrate the abandonment issues from “Replacement Girl,” and “Too Good,” and “Child’s Play,” which find The Boy still pleading his case and promising to change his player ways as in “Think Good Thoughts.”

The latter is also notable for being one of the two songs that feature one of Drake’s primary inspirations: Phonte Coleman of Little Brother appears both solo on “Good Thoughts” and with his Little Brother rhyme partner Big Pooh on “Don’t You Have A Man.” It’s clear how much Phonte’s verbal quirks inspired Drake then and continue to do so now. Before Drake’s quasi-confessional overshare became the prevalent rap style du jour, Phonte crooned and mooned his way through two Little Brother albums and a project with The Foreign Exchange, providing proof of the concept Drake would capitalize upon in his next outing, So Far Gone.

The roots of Drake’s connection with Lil Wayne also found their genesis on Comeback Season‘s closer, “Man Of The Year,” a “freestyle” over Brisco’s mixtape track of the same name which featured Drake’s future mentor. It was this track that Jas Prince used to convince the skeptical Weezy F. Baby to give the then-bubbling Canadian rapper an opportunity. Wayne was so impressed by Drake’s work on this final song that he paid to fly Drake out to participate in his Tha Carter III tour. Their work on that tour would eventually lead to Drake’s deal with Young Money Entertainment and his takeover of hip-hop. None of that happens without Comeback Season.

Of course, other hallmarks of the former actor’s style are present throughout the mixtape as well. His penchant for semi-corny wordplay is evident on songs like “The Presentation” and his “Barry Bonds” freestyle; behold lines like “I’m cutting lights out like it’s bedtime / These other rappers lukewarm like red wine,” and “Bar Mitzvah kid, get your hits destroyed / Cause I keep it under wraps like Christmas toys.” However, just as evident is the drive to impress that inspires his more lyrical offerings like his “AM-PM Series” tracks that often prompt calls for him to release full-on rap albums. On “Going In For Life,” “Where To Now,” and “Closer,” he casually floats over classic production from J Dilla and custom beats from Boi-1da and T-Minus — his future hit-making partners on tracks like “HYFR,” “The Motto,” “Controlla,” and more.

In hindsight, it was clear that Drake had all the ingredients for the success that was soon to follow him, and Comeback Season laid the groundwork for that success. There’s a reason that his omission from the 2009 XXL Freshman list generated such a public outcry, months before the release of So Far Gone. It’s because Comeback Season called Drake’s shot while displaying all the confidence in the world that he would knock it out of the park. The rest is history.