Mixtape Primer: Drake's Pre-Fame Output and Post-Fame Return

Navigating the Toronto rapper's output from 2006's 'Room for Improvement' to 2015's 'What a Time to Be Alive'

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Mixtape Primer: Drake's Pre-Fame Output and Post-Fame Return

Drake is such a unique talent that he resists comparison. Sure, there are many who anticipated the Toronto rapper's unique blend of supper-club pop crooning and angsty braggadocio, from Big Daddy Kane and Slick Rick in the golden age; to Snoop Dogg, Ja Rule, 50 Cent and Andre 3000 during the gilded club era of the new millennium. Lil Wayne soaked Tha Carter III in Auto-Tune, but didn't pretend he was a pure singer. Kanye West did the same on 808 & Heartbreak, but never claimed to possess battle-rap skills.

Guide: 
**1/2 Room for Improvement (2006)
*** Comeback Season (2007)
**** So Far Gone (2009)
**** If You're Reading This It's Too Late (2015)
***1/2 What a Time to Be Alive (w/Future) (2015)

Despite this, Drake continues to be criticized by hip-hop purists for the way he combines singing and rapping. Much of this suspicion is sourced in his origin as a successful lead actor in the Canadian teen ensemble Degrassi: The Next Generation. Cash, fame, TV-ready good looks and well-trafficked MySpace page gave him an advantage, but Drake also had the artistic and business savvy to make it worthwhile. His early mixtapes are instructive for anyone who doubts Drake's distinctive status in post-millennial rap: They prove that his sound wasn't hatched in a corporate boardroom, but developed through trial, error and a little bit of luck.

Room for Improvement, which is "hosted" by DJ Smallz, a Florida DJ known for his Southern Smoke series, reflects Drake's formative experiences in Toronto's then-underexposed rap scene. Many who encountered or worked with him during this time admit they initially dismissed him as an actor "moonlighting" as a rapper, but were eventually won over by his skill and work ethic. Even at this stage, he clearly knew how to put bars together. "Rappers they tend to be smiling because these women are women, most of them seeking favors/They come in secret flavors/That's why I envy Omar because I'm nowhere close to Malik and Deja/And that's some Higher Learning," he observes on "Thrill Is Gone," a standout song with a buttery, soulful tone made by Canadian producer Amir. But his voice in 2006 sounds a little stiff – for all of his subsequent success, Drake has never sounded as effortlessly graceful as peak Jay-Z, for example. He tosses up some groaners, too. "And no, this ain't Blu Cantrell/This is like perfection/Though we both got the light complexion," he claims on "All This Love."

Despite its wood-shedding quality, Room for Improvement is modestly entertaining. With contributions from Canadian producers like Slakah the Beatchild, Frank Dukes and Boi-1da, it's typical of the backpack rap and chipmunk soul that flourished in indie and underground circles during the mid-Aughts. Only "City Is Mine," which tries to mimic the Houston rap sound with some success, portends how he'd later hybridize musical styles into a lushly appointed tapestry. "This the record that my backpack underground fans get to skipping/Back back, Southern town fans get to tippin'," he brags.

The tape's peaks mostly arrive with help from Nickelus F, an underground veteran from Virginia that Drake recruited via MySpace. As a battle MC who's early fame mostly drew from winning national competitions like 106 & Park's "Freestyle Fridays" on BET, he virtually takes over the ConFunkShun-sampling "A.M. 2 P.M." with a burner verse, then spurs Drake to greater heights on "A Scorpio's Mind" and "S.T.R.E.S.S."

After Room for Improvement, Drake continued to build momentum. DJ Smallz referred him to Louisiana entrepreneur Terral T. Slack, who subsequently became his manager and helped arrange recording sessions with rising R&B star Trey Songz. Other high-wattage cameos like Malice from Clipse (who jumped on a remix to Room for Improvement's "Do What U Do"), neo-soul veteran and frequent Kanye West collaborator Dwele ("Don't U Have a Man") and Canadian hip-hop pioneer Kardinal Offishal ("The Last Hope") ensured that the aptly titled Comeback Season would resonate beyond MySpace and Okayplayer.com's message boards. As a result, Drake and Trey Songz' bubbly urban pop confection "Replacement Girl" became the first video by an unsigned Canadian rapper broadcast on BET.

Yet sonically, Comeback Season doesn't deviate sharply from Room for Improvement. A key moment arrives when Drake sings for the first time over the crunchy funk of "Bitch Is Crazy." He sounds fine, but quickly passes it off as a joke. "I wanna sing in the rain, girl," he crows. He sounds much more comfortable on "Think Good Thoughts," where he trades bars with Phonte over a 9th Wonder loop that makes marvelous use of Anita Baker's "Sweet Love." That track reveals how much Drake drew from Little Brother's ingenious melding of Pete Rock-styled grooves and lush neo-soul, even though too many mainstream critics harped on LB's stylistic choices during their too-short career.

While the first half finds Drake on familiar territory, much of the second half is dedicated to Swizz Beats-inspired club bangers. He tries to ball out on "Asthma Team," bragging, "Commode you rappers like plasticine," and "Stop acting like teen girls is my only market." For "Man of the Year," he re-appropriates Flo Rida, Brisco and Lil Wayne's mixtape track, only he cuts the first two MCs verses out, leaving the appearance that he's in the studio with Weezy alone. It's a gauche effect, but, hey, that was mixtape culture in the Aughts.

Furthermore, the baiting tactic seemed to work. Buoyed by a rising Internet profile – MySpace named Drake the most popular unsigned Canadian artist – he took meetings with various majors. One with Universal Motown president Sylvia Rhone went disastrously, and he subsequently dissed her on his next mixtape, So Far Gone. (He apologized for his lines on "Say What's Real," but two years later, he criticized her again at the BMI Awards for "not believing in" him.) Most importantly, he traded calls with James "Jas" Prince, son of Rap-A-Lot Records founder James Prince. Jas connected Drake to Lil Wayne, who eventually pegged the unsigned rapper for his Young Money imprint. Jas was eventually elbowed out of the financial picture, resulting in years of litigation.

The backroom machinations as well as Lil Wayne's mentorship set the stage for Drake's creative and financial breakthrough. From the first warm, hazy synthesized notes of "Lust for Life," it was clear that So Far Gone was treading into new territory for a rap release. Other rappers were attempting similar experiments – both Kid Cudi's A Kid Named Cudi tape and West's 808s & Heartbreak exerted a marked influence on Drake's new direction. But while Kid Cudi harmonized in a deep, slightly unmoored rumble, and West and Wayne stretched their Auto-Tune-enhanced voices to their emotionally cracked limits, Drake smoothed his into a light, slightly melancholy croon. His singing inflections closely resembled Trey Songz, but without the latter's range and gospel-trained melisma. As a combination of winsome melody maker and energetic rap boaster, Drake evolved into something entirely unique.

Just as key was the friendship he built with Noah "40" Shebib, another former actor who focused on music after childhood appearances in Canadian films and TV. 40's engineering and production techniques led to a translucently ambient sound that enveloped the hour-long So Far Gone, and underlined Drake's sexual and career ambitions. The sparkling, soft-focus rendering of Boi-1da's beat for "Best I Ever Had" cleverly contrasts with Drake's roguish rhymes about cheerily lying to women after making love. Even clichéd blog-rap era tricks like sampling indie-pop hits get renewed life. Instead of simply ripping off the hook from Lykke Li's "Little Bit," Drake crafts a duet by singing alongside her voice. His newfound singing abilities nearly overshadow his improvement as a rapper, and he embodies the contradictory impulses of ridiculous boasting and disarming, self-deprecating honesty – a trait that listeners would soon term "humblebrag." "As a man, I'm just honest, as an artist I'm a king/With my own set of problems that be sittin' on my brain," he raps on "The Calm," a prime example of the chorus-less, soliloquy-styled tracks that briefly flourished in online rap circles. For "Brand New," he asks plaintively, "Is anything I'm doing brand new?"

Months after So Far Gone's mixtape release, Universal reissued it as a seven-track EP. This second version cuts out some of the original's less successful numbers, like an unnecessary remix of Santigold's "Unstoppable," while reducing the project to its memorably romantic core. It does add two new cuts – "Fear" and "I'm Goin' In" – but it also omits some of the mixtape's strongest moments, particular "Ignant Shit," where Drake and Lil Wayne go hard over Just Blaze's uptempo loop of the Isley Brothers' "Between The Sheets." If you need proof that Lil Wayne deserved his title as one of the best rappers of his day, then lines like, "No, I didn't say that I'm flawless/But I damn sure don't tarnish" will surely suffice.

In the next half-decade, Drake would become a superstar, making three chart-topping studio albums, racking up numerous Gold and Platinum awards, headlining tours and launching the OVO Sound record label. But in 2015, Drake made a surprise return to the mixtape form. If You're Reading This It's Too Late is a startling assertion of his under-recognized prowess as a rap lyricist. It teases out some of the hardened turnt-up moments of his previous work, 2013's Nothing Was the Same, while offering pushback against intractable critics and haters who doubted his artistic ability. It sounds like an angry statement of purpose.

"Drake has often been synonymous with emotional openness, but this is far and away the least vulnerability he's ever shown on record," wrote Simon Vozick-Levinson in his Rolling Stone review, "at least until "You & the 6," a heartfelt, one-sided conversation with the single mother who raised him. He complains about the time she tried to set him up with her personal trainer; he pushes her to forgive her ex, his dad. It's one of Drake's best songs ever, but you might not notice it until the third or fourth listen because he plays it so cool. For the first time in his career, Drake doesn't sound like he wants to be remembered as one of the greats. This time, he just is."

Later in 2015, Drake dropped a second mixtape, this time a full-length collaboration with Future. If You're Reading This is angrily intense, but What a Time to Be Alive is a frothy, playful jam session between two current icons. Not coincidentally, Future had recently dropped his widely hailed DS2, a conflagration of raps about drug use and fracturing relationships. Perhaps What a Time to Be Alive was an opportunity to relax, with hit records (in the form of "Jumpman") as a nice bonus.

"What a time to be alive – and being 'alive,' as Future and Drake define it, involves having way too many feelings about way too many strippers for way too many sleepless nights," wrote Rob Sheffield in his Rolling Stone review. "Their surprise mixtape collabo is shrewdly timed, since both MCs are on a creative roll after dropping two of the year's biggest and best albums. It's a quickie and it sounds that way: a six-day digital dash in the studio. Yet that's why it feels fresh and spontaneous. This is the sound of Future's Dirty South meeting Drake's Great White North, both artists playing off their louder-than-life personalities without overthinking the details."