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Drake | A Sad Boy Story

Updated: Apr 2, 2020

My name is SkipFromBk and I am a Drake fan. Years ago, I was an obnoxious stan (I was notorious amongst my circle of friends for the Drake love). I state these facts to let you know, I am not writing a review on the More Life playlist. Instead, I would like to do a quick write up on the stages of Drake to showcase how he got to his present form. This is Drake A Sad Boy Story.

Wheelchair Jimmy (2006-2009 | Room for Improvement/ Comeback Season/So Far Gone

At the beginning of our story, we have our origin story consisting of the awkward phase to find yourself. These are the years of finding what works and minimizing what doesn’t. The first two mixtapes in Drake’s career displayed the hunger every rapper we know possesses. He wants the respect of his peers, adoration from his idols, and the love of the women who shunned him years before. The witty phrases and slick bravado is sprinkled all over these projects.

This time frame tends to be the version of Drake people miss the most. We did receive Drake’s most timeless piece of work which was So Far Gone. I feel it is always going to be a top three Drake project no matter what comes out in his entire catalog. If a fan says otherwise, they are NOT a fan. I feel you have to admit, his progress in this era was exponential. Room for Improvement is Charmander, Comeback Season is Chamelon, and So Far Gone is a fully formed Charizard. This is our prologue to the Sad Boy Story.

Drizzy Sipping the Swag Juice (2009-2011 |Thank Me Later)

The confidence boost Drake gets by signing with Young Money as well as going toe to toe with prime Lil Wayne (at some points besting him) creates a conflict in our Sad Boy Story. Drake is now getting the attention from the ladies and obtaining the type of money he dreamed about. His insecurities are flaring up at an alarming rate. To depict this accurately, let’s use my favorite song from Drake (Fear) which displays how the boost in status affects the people around you. The vulnerability people love from his music is now being used against him. He felt suffocated and is starting to glance back at how “simple” his old life was before the fame.

Unfortunately, Thank Me Later was a subpar album and has a sound you don’t normally hear from Drake’s recent works. Drake is working with people on that album he doesn’t normally work with. You can hear it in the sound and lack of chemistry track to track. This project also does not have 40 (Noah Shebib) with sole custody of the musical direction of the album. It is a muddled compilation and is the start of Drake realizing it takes OVO to make Drake sound amazing.

The Leap from being a Starter to an All Star is harder than it looks (2011-2012 | Take Care)

By the time Take Care was released, Drake’s name had obtained enough notoriety to have his name listed with the folks he always looked up too. The fans want a great album and indeed they received a great album. I know I have been writing about Drake Sad Boy Story but we have to understand how important 40 is to the process. This album 40 has his name on a majority of the music. He has full control of the behind the scenes decisions making him the Alfred to Drake’s Bruce Wayne. This is crucial to the cultivation process of the sound that is Drizzy Drake. We can exclaim this is prime Sad Boy Drake vibes.

Take Care is a magnificent piece of work and goes into a more realistic depiction of Drake. People exclaim this is probably Drake’s best work (I still lean towards So Far Gone). The Drake style is reinforced discussing his relationships with his family/friends/lovers/future lovers/past lovers/etc. We can easily admit the range of his songs are on everyday things people wonder about in their free moments.

The Megaman style originates from this album and carries over to future projects. If you have no idea who Megaman is, here is a quick synopsis. He is a robot who uses powers he gets from people he has previously defeated to overcome a final boss.

Does Drake slay rappers?


Does he learn some new styles from others to add to his own sound?

Yes, he does.

With newcomers The Weeknd and Kendrick Lamar on this album, we begin to notice Drake looking around to keep learning to climb the ladder to the top. Sad Boy Story goes from worrying about the money to worrying about the legacy.

Champagne Papi is born (2013-2015 | Nothing Was The Same/If You’re Reading This It’s Too Late/What A Time To Be Alive)

This era is where Drake supersedes Lil Wayne as the go-to chorus killer on the hottest tracks during this time frame. His insecure side is on the back burner and the grandiose I have money side is taking over. Drake is even spotted in the gym from time to time. Let’s start with Nothing Was The Same which is the last of the top 3 projects in my opinion.

What I love about Nothing Was The Same was the hidden journey in the album by playing the album backwards. Not backwards as in trying to hear sounds like you are in a horror movie. I mean you literally play the album as if Pound Cake was the first track and Tuscan Leather was the last track. You will understand the Memento reference in Tuscan Leather and the way each direction generates a different sensation. If you play the album the right way, you are climbing up till the Drake and Jay duet on Pound Cake. If you play the album the bonus style way, you get a descent of falling inward. It feels like you are in the movie Inception falling into limbo.

While Drake completed owning 2014 with NWTS, he goes into 2015 with two surprise compilations. The first was If You’re Reading This It’s Too Late and it was an experimental mixtape. This is the project he had a “writer” help him with some songs and causes people to question Drake’s legitimacy as a writer. IYRTITL isn’t one of my favorite pieces but it does induce Drake to go from Sad Boy to Angry Sad Boy when Meek Mill shoots his insults via twitter and IG. You can say the first is the reason the second (What A Time To Be Alive) was created. If Meek never came for Drake about IYRTITL who probably would have received a different depiction of Views.

Who knows? I do know these two projects had some great singles but did not possess the typical Drake flair the previous albums had to make you want to stay for more. This is crucial to note because it feels like Drake is coasting here. He is comfortable and feels untouchable until (wait for it) he is bothered. The musical direction has been pushed in a different direction. Thanks Meek (or maybe no thanks Meek).

You Either Die A Hero, or Live Long Enough to See Yourself Become The Villain (2015-Present | Views/More Life)

This is our present rendition of Drake and let’s say he isn’t on everyone’s nice list. Over the course of his career, he has started out as the underdog, headliner, and now is a powerful figure looking down on the populace. He has been in the gym seriously and he has no traces of Wheelchair Jimmy on his current person. The confidence and sureness in his moves has our Sad Boy not so sad anymore. People root against him and he retreats to his Drake Cave in the land of the 6ix. Views was sparked by his beef with Meek Mill and the need to go back home. To reconnect and recharge in the one city he understands. The place he calls home and harnesses the energy of the city to spread his influence globally.

As I mentioned earlier, Drake over time has worked with a ton of people. He has always added portions of those bits of energies to his to make his style evolve over time. Some people call it stealing and others will call it evolution. The point is Drake has traveled to other parts of the world to gain inspiration for new music. He indirectly gives kudos to these areas and the artists of the region through his music. I will admit he does credit some and doesn’t credit others. This is part of the fuel on why he is vilified so much in his moves.

More Life is a step back to the Drake of the Take Care/Nothing Was The Same era. The features were sonically “right” and he created experiences instead of following others. He came full circle through his everlasting Sad Boy journey to get to the place he is at currently.

Will our boy wonder finally get the girl of his dreams?

Will he achieve everything he desires?

Is he the next Jay-Z?

Will the sadness ever go away?

I honestly have no idea. I do know I have enjoyed his transformation over the years in his artistry. Only he knows what he has planned next. I look forward to the next chapter to the ongoing Sad Boy Story.

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