The storylines, notable bars, highs and lows, and impact of Drake's second official mixtape.
It's easy to imagine Drake as the all-powerful artist he is today, but Comeback Season tells a different story— Comeback Season tells the true story of Drake.
The most successful hitmaker in history was once an unsigned rapper, operating under the shadow of a Degrassi fan favorite, relying on Trey Songz for fans and marketing stolen Lil Wayne samples as features.
20 seconds into Comeback Season, Drake attacks the shadow of Degrassi, rapping "they like 'Damn who's Drake? Where's Wheelchair Jimmy at?' On my Chris Brown shit, I'm still here, gimme that."
As the bar references, Drake wouldn't leave Degrassi for another year post Comeback Season, but the 23-track mixtape was the project that started the tilt from Wheelchair Jimmy to Drake, despite Degrassi still being the lane that actually paid.
Comeback Season and the media that surrounded the mixtape is a collection of present-day Drake easter eggs, making it the perfect project to use as a lens into one of the biggest figures in rap history.
Storylines
The above video by ET Canada is like a trailer to Comeback Season.
It's slightly awkward yet admirably honest. There's a 40 reference. There's a Trey Songz reference. Degrassi gets brushed aside quickly. And Drake spends nearly half the interview focusing on women.
The most important clip from the trailer is Trey Songz.
Drake's decade plus of success combined with Lil Wayne taking over as his mentor basically erased the Trey Songz' chapter out of the Drake history book, but before there was Wayne there was Songz.
I could probably type a thousand words on the role Trey Songz played in getting Drake off the ground, but this video by HipHopDX sums it up better than any word count could.
Songz is on four Comeback Season tracks. For context, Lil Wayne was featured on So Far Gone four times, but unlike Songz, Wayne was directly profiting off the success of Drake's career, being on four songs for him was making sure his investment would pay off.
Trey Songz being featured on an artist he had no financial ties with, regardless of what Drake was willing to pay, was unprecedented. It reveals that Songz truly believed Drake was on the verge of something special.
On "Underdog" and "Give Ya", Songz raps and sings, something Drake doesn't try for the entire project, but it's clear Drake is the reason. In the ET Canada video, Drake points out how he wrote the "Replacement Girl" hook before ever meeting Songz, yet the actual song only has Songz performing.
Drake already sees the potential in infusing Hip Hop and R&B like never before, but at this early stage of his career, he doesn't trust himself to do it, so he tags in Songz to test his hypothesis throughout Comeback Season.
The fact that Songz didn't run off with Drake's hypothesis or finesse him into a terrible deal says a lot about Songz.
Three Most Notable Bars
"How the fuck Jay and Dame gon' break up 'fore they meet Drake?" (The Presentation)
This is one of three interesting Jay-Z-related bars on "Comeback Season". Drake crowns Hov as Michael Jordan and himself as Pippen on "Going In For Life" and talks about how Roc-A-Fella tried to sign him twice on "Think Good Thoughts". The bars on "The Presentation" and "Going In For Life" are notable because it shows the respect Drake has for Jay-Z, which makes their never-ending cold war of jabs that much more interesting.
This respect also makes it unbelievable that Drake would turn down two Roc-A-Fella offers, considering he was practically begging Trey Songz to sign him at the time. So was Drake lying for clout? Most likely, especially when you factor in the fake Lil Wayne feature on "Man of the Year" and what it took for Kanye West to get signed as a rapper to Roc-A-Fella.
But for the sake of rewriting history, let's pretend Drake really did get his dream offer.
He obviously accepts in a heartbeat. The 2007 timeline means 808's & Heartbreak was still being created, and there's no way a new signee with the pen talent, interest in love and devotion to fusing Rap and R&B elements like Drake isn't involved. Drake would even go on to release a gem-filled mixtape titled Heartbreak Drake in 2008 with the first song being a remix of West's "Say What's Real".
If Drake is on the roster for 808's & Heartbreak, does Kid Cudi get recruited for the project and become a legend in his own right?
Another major what if is J.Cole. Cole was shot down by Jay-Z in 2007 and wouldn't sign to Hov until 2009. At the time, Jay-Z's intention was for Roc Nation to be a Pop label, but hearing Cole made him pivot plans.
Would Drake have sparked that same pivot or would Hov have doubled down on his Pop stance after hearing Drake's potential? Where would Cole be if Hov chose Drake as his rapper protege for the next generation? How many hits would Drake and Rihanna have under the same label? What about Lil Wayne and Young Money? Could Nicki Minaj alone lead Young Money next to Wayne, and if so, how much further would she have ascended if she was the only marquee star on roster?
It's safe to say music as a whole would be completely different if Drake actually received an offer from Jay-Z in 2007.
2. "You hatin' my songs, but your wife wanna burn it"(Do What You Do)
Drake makes it clear throughout the mixtape that he knows the potential he has with women fans, but this line is equivalent to 14-year-old LaMelo Ball pointing to the halfcourt line before pulling up.
It's young Drake accurately predicting his success and backlash before either arrive.
The line predicts the inner battle with himself and the outer battle with other rappers that he'll face across his entire career. It's the reason Scorpion has 25 tracks. It's the reason Drake jumps at any jab that comes his way. It's the reason he ghostwrites for Baka and angrily runs into clubs to fight. Drake knew from the very beginning that the formula he laid out would turn him into a cheat code, the rapper who women love the most.
Regardless of what male-dominant social media conversations attempt to push, women are the gatekeepers and tastemakers of mainstream rap. Whether you trace it back to late-night clubs, viral TikTok challenges, online fanbases, or screaming fans at tours, artists need female support to crack the superstar barrier. There's a reason why Russ can go platinum with no features despite having little support from men, and "Wet Dreamz" and "Workout" take up two of J.Cole's top-5 most streamed songs.
Nothing goes Pop without women, and Drake knew that from day one. But that doesn't mean he was ever fully comfortable with it.
"Telling people my image is lame, and I'm what's wrong with the game, but I'm feelin' like (you must hate money, money)," raps Drake on "Must Hate Money".
3. "They can't audit if they don't know I bought it"(Going In For Life)
Conspiracy Theory: Whenever the day comes where Drake attempts to fully own his masters, a report will come out that he owes around nine figures in taxes.
Between this track from 2007 and 2020's hit single "Life Is Good", Drake has two explicit tax fraud confessions. "Life Is Good" is one line of confessions and could probably be thrown out by the type of lawyers that Drake can afford, but if the IRS ever comes into contact with the first verse from "Going In For Life", Drake is going to prison after about 10 seconds of deliberation.
As if he's doing his best Druski or Key & Peele impression, Drake comically goes into great detail about his crime:
I don't want SoundSports to have a DJ Vlad reputation, so if the day ever comes where my conspiracy theory prediction becomes reality, this article will self-destruct.
Aged The Worst: The Hooks
The hooks on Comeback Season are easily the worst in Drake's entire discography.
Outside of bars like "anticipated like the iPhone", the only time when the project truly feels dated is through its hooks. From unnecessary filters to over repetition, Drake falls into a lot of the hook traps that catch young artists.
On "Must Hate Money" he relies on a deep voice filter for delivery, "Faded" features a hook that simply repeats the title over and over again(ahead of his time in that sense), and "Missin' You" has Drake(maybe) doing a weird robot voice.
As bad as those hooks are, they're expected from a young rapper, but the "Do What You Do" hook is unacceptable from an artist that was writing on Dr. Dre's Detox around the time.
Drake raps, "Stance on lean, leg up on the wall, My people they chill, why you haters wanna ball, I'm satisfied with a little, why you haters want it all, You waiting for the Spring, and I'm gettin' it in the fall, But uh, do what you do what you, I do what I do, Do's what you do, I do what I do."
The hook ruins the song with the best feature(No Malice) and is easily what aged the worst on Comeback Season.
Aged The Best: Drake's Confidence and Mixtape Era
I'm not old or white enough to have witnessed Babe Ruth point to the crowd before blasting a home run in the very destination he predicted, but I imagine listening to Comeback Season is similar to how watching that would have felt.
In an episode of The ETCs with Kevin Durant, Noah "40" Shebib is asked if he ever thought he and Drake would blow up the way they did and he says he used to look at Drake like he was crazy when he would predict their future. I had to stop the project several times because of how crazy Drake's predictions were, but unlike 40, I thought they were crazy because of their accuracy.
Comeback Season is like a giant Simpson's episode of Drake telling the listener, either directly or through his song choices, exactly how his career is going to turn out. He even predicts his 2009 breakout success on "Where To Now", rapping "if '09 is when I'ma see mine, Being cool ain't enough, homie; I'ma freeze time."
The other aspect that aged best was the mixtape era elements of "Comeback Season".
Drake ends songs abruptly because he didn't pay for the beat("Think Good Thoughts"), remixes Kanye West's "Barry Bonds", preludes the next track at the end of the current track("City Is Mine") and gives a spoken thank you for listening message at the end of the mixtape. Streaming and the elimination of CDs has made most of these practices extinct today, so it's refreshing to revisit how connected the artists were forced to be in the mixtape era.
Reviews
Since Drake wasn't signed to a major at the time and due to Comeback Season being released during the blog era, there's not any critical coverage of the mixtape from the time.
The most timely reviews I could find came from Rate Your Music, and they averaged out around 3 out of 5 stars.
The most detailed review came from a user named dashfort who had this to say:
While the review is too biased to count as the best review of Comeback Season, it's the perfect example of how polarizing Drake and his R&B-style was viewed in Hip Hop before he would go on to popularize it.
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