Round 1
(8) No Tellin' vs (9) Over My Dead Body
I think "If You're Reading This It's Too Late" is one of Drake's most underrated projects and remember thinking highly of "No Tellin'". Going back and listening to it left me a little disappointed especially compared to some of the songs I've already had to eliminate while making this bracket. "Over My Dead Body" on the other hand still gives me the same feeling as it did when I heard it for the first time. Drake really can't miss when it comes to album intros can he?
Winner: (9) Over My Dead Body
(4) 0 to 100 / The Catch Up vs (13) Two Birds, One Stone
A matchup of two non-album singles. "0 to 100 / The Catch Up" is another case of Drake being able to basically incorporate two songs into one. A lot of people seem to know about the first half but lesser so the second half which I think is arguably better than the prior. "Two Birds, One Stone" is also somewhat unknown but focuses on Drake sending veiled shots at Pusha T, Meek Mill, and Kid Cudi with an onslaught of bars. "0 to 100 / The Catch Up" is clearly the better song here though.
Winner: (4) 0 to 100 / The Catch Up
(5) All Me vs (12) A Keeper
So there's a version of "All Me" that has an extra Drake verse at the end but for some reason this isn't the version that's on streaming. Drake's verse is just arrogant and as corny as it is, his "I'm on a roll like Cottonelle is was made for all of this shit" is pretty damn clever. Drake's experiment into electronic music has its sole representation in this bracket through "A Keeper". As I've said many times before I really do like this exploration into new sounds by Drake, I don't think he's perfected his version of this sound yet but I think it's a fun song nonetheless. "All Me" wins this one.
Winner: (5) All Me
(7) Summer Sixteen vs (10) Tuscan Leather
I think "Summer Sixteen" might be one of Drake's most disrespectful but also musical songs in the whole beef with Meek Mill. His line regarding how Meek doesn't need to "say it louder" always makes me laugh for how clever of a slight it is. He even finds some time to hit Tory Lanez with a few bars as well. "Summer Sixteen" is a great song but the only issue here is that it's matched up against another one of Drake's intros in "Tuscan Leather". Complete with multiple beat switches and even more flow switches, it's no doubt that "Tuscan Leather" would come out the winner here.
Winner: (10) Tuscan Leather
Drake starts off "HYFR" with such a unique and intricate flow that's damn near manic which he appropriately breaks out of with the line "texted and told her I'm faded". He shows off his breath control (or a really talented recording engineer) on that first half of the verse and his chemistry with Wayne is on full display as they mesh incredibly well on this track. The previous track on Take Care "Look What You've Done" has a very contrasting vibe and features Drake over a minimalist beat structured around a muted piano sample as he pays a touching tribute to some of his family members. "Look What You've Done" is sentimental but "HYFR" is far and away the winner in this round.
Winner: (6) HYFR
Round 2
(1) Passionfruit vs (8) Over My Dead Body
I know I've been consistent about eliminating these pop hits from the bracket but "Passionfuit" I think is a song that captures the feeling of warmth and summer so perfectly. Drake breaks out his soft R&B voice for this one which meshes so perfectly with the beat. I do enjoy "Over My Dead Body" as an intro but as a standalone track and against a juggernaut like "Passionfruit", it's over for "Over My Dead Body".
Winner: (1) Passionfruit
(4) 0 to 100 / The Catch Up vs (5) All Me
Battle of the beat switches on this one. I feel like Drake gets deeper into his braggadocios persona on "0 to 100", his bar about the [Toronto] Raptors paying his bills is such a ridiculous flex. He has such a level of confidence and arrogance on this song and considering his rapid ascent up to that point in 2014, it was extremely justified. He has a similar fire on "All Me" but I think the all around performance on "0 to 100" is much better. And that's all without mentioning how spectacular "The Catch Up" is. We're putting the two part track through once again.
Winner: (4) 0 to 100 / The Catch Up
(2) Laugh Now, Cry Later vs (10) Tuscan Leather
Another "radio" record in "Laugh Now, Cry Later". This one isn't as blatant as others but I'm truly shocked at how popular this song got; 800 million streams isn't anything to laugh at. He makes another fun record with an even more fun music video that is absolutely star-studded. "Tuscan Leather" may have just over 10% the streams of the previously mentioned song but Drake's performance more than makes up for the difference in popularity. With three distinct musical sections and three completely different flows packed with quotables, "Tuscan Leather" wins here.
Winner: (10) Tuscan Leather
(3) Marvin's Room vs (6) HYFR
Well finally here's the Goliath of this bracket. If there was a university level course on throwing another man in the dirt to get the woman you want "Marvin's Room" would definitely be a key part of the syllabus. From the now iconic "are you drunk right now" voicemail, to the "cups of the rosé" that starts off the song it's hard to find someone who can deny the impact of this record to Drake's popularity and more importantly -- his image. I'd go as far as saying that it's this song in particular that solidified Drake as the "emotional rapper" that he's constantly known as; a monicker that has proven difficult to shake. "Marvin's Room" unsurprisingly wins.
Winner: (3) Marvin's Room
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