Here's what went down in Group 4!
Round 1
(8) 9 vs (9) Star67
Not only is "Star67" the number you dial to make your number private, it's also a cheat code in this bracket. Drake makes a song centred around phone scamming and him being scammed by his label sound absolutely beautiful. He goes from angry to nostalgic to almost dreamlike in the span of 5 minutes. Sensational track. "9" also has some great musical moments and has Drake coming alive with an incredible amount of energy but it also has some shortcomings *ahem* "keychain go jang-a-lang, I wanna do major thaaaangs". Winner is obvious in this matchup.
Winner: (9) Star67
(4) Know Yourself vs (13) 4pm in Calabasas
Drake intended for "Know Yourself" to be a song for Toronto similar to how "Black and Yellow" by Wiz Khalifa was a song for Pittsburg. I'd be more than comfortable saying he succeeded having been living in Toronto right around the height of this song. The amount of Tweets, Instagram captions, and people straight up saying they're "running through the six" showed the sheer impact of this song. "4pm in Calabasas" is just a mean song though. It's another case of Drake's classic [time] in [place] series where he just raps straight through and is usually pretty angry and addressing something frustrating him at the moment. Drake quotes and then explicitly disses Diddy as well as numerous others in the industry. "Know Yourself" was a great song for the city but is unfortunately met its match in this bracket.
Winner: (13) 4pm in Calabasas
(5) Jungle vs (12) March 14
"March 14" is a bit more of nasty work from Drake as he spends the beginning of the track airing out all of his dirty laundry around the conception of his kid. He uses the second half of his verse to flip the track and start talking about how he eagerly awaits the opportunity to raise his son in a way his own father couldn't. Genuinely though, "Jungle" is in a class of its own when it comes to Drake's catalogue. The beat is damn near flawless, the vocal performance is incredible, and the storytelling is phenomenal. It's the winner here.
Winner: (5) Jungle
(7) Shot For Me vs (10) Keep The Family Close
I don't feel super strongly towards either of these songs. "Shot For Me" is an excellent song that captures the tone of the first half of Take Care pretty well and the second half of the track features a solid Drake verse. "Keep The Family Close" being an intro feels almost cinematic especially with the minimal instrumental backing during the first two minutes before the song starts to open up. I think Drake's delivery and tone on "Keep The Family Close" is slightly better so I'm going to have to rock with that one.
Winner: (10) Keep The Family Close
I always associate "Sneakin'" with Halloween which makes sense considering it dropped exactly a week before the 31st. You can definitely say the beat is pretty spooky and would more closely be associated with 21 Savage rather than Drake. This was the first time the duo of Drake and 21 did a song together so it made sense Drake had to show out with some clever bars and metaphors. The baseball references on "Connect" are all pretty clever as Drake struggles with a toxic relationship he badly tries to make work by constantly just "swinging" away with attempts to fix it. Both songs here are great but I have to go with "Sneakin'" in this matchup.
Winner: (6) Sneakin'
Round 2
(1) Hotline Bling vs (9) Star67
We all know how popular "Hotline Bling" was and what a moment it was for Drake as a popstar but in good faith I cannot and will not let it go any further in this bracket considering what I said previously about "Star67".
Winner: (9) Star67
(13) 4pm in Calabasas vs (5) Jungle
I hate this matchup so much. "4pm in Calabasas" is definitely one of my favourite songs in Drake's discography so it going up against "Jungle" is truly tragic. "Jungle" is for sure the better song here and I've sung its praises already in this bracket. If I could cheat and smuggle "4pm in Calabasas" in further I absolutely would. "Jungle" wins.
Winner: (5) Jungle
(2) Hold On, We're Going Home vs (10) Keep The Family Close
"Hold On, We're Going Home" enjoyed a bunch of commercial success and is far and away the most popular song off of Nothing Was the Same and for good reason. I don't usually rock with these pop records but "Hold On, We're Going Home" just has a retro feel that just oozes warmth and comfort. If you've ever taken a car ride at night or been in a club late night with this song on you know what I mean. His vocal performance on this is also quite great and he just sounds so comfortable over the beat. It's the clear winner here as well.
Winner: (2) Hold On, We're Going Home
(3) The Motto vs (6) Sneakin'
Drake wastes not a single bar on "The Motto" coming in right at the 1 second mark of the track with a level of arrogance he hadn't particularly displayed up until this point in his career. Pick almost any bar in isolation on this song and it absolutely captures Drake's overall demeanour here. It's a bonus track on Take Care and rightfully so since it don't match the rest of the album in tone or energy at all but was this ever a cultural moment and brought the term "YOLO" to the forefront of culture. Drake raps well on "Sneakin'" too but it's a lot more impactful on "The Motto".
Winner: (3) The Motto

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