17. Man of the Year (2007)

17. Man of the Year (2007)

Lil? Wayne and Drake reunited for a cut off of Dedication 6 with a freestyle over Jay-Z?s ?Family Feud.? It marks the 38th time the Young Angel and Young Lion have appeared alongside one another on wax; the 17th song they?ve recorded as a duo. To put things into perspective, hip-hop?s most celebrated bromance ? Jay-Z and Kanye ? have collaborated on 20 songs, 16 of which came by way of their joint album, Watch the Throne. Drake and Wayne?s partnership is much more consistent.

Since 2008, Drake has featured on eight Lil? Wayne songs; Wayne, nine of Drake?s. Their alliance peaked from 2009?11, a period in which Wayne was unanimously viewed as the best-rapper-alive, while Drake was rapidly ascending into hip-hop?s upper echelon. Over this three-year stretch, both MCs were present on each other?s solo offerings. On Drake?s 2009 mixtape, So Far Gone, Wayne featured on five tracks; Wayne?s 2010 project, I Am Not a Human Being, found Drake as a guest on three; they linked up on Thank Me Later?s ?Miss Me?, before, in 2011, Wayne appeared on three songs off Take Care, while Drake participated in two on Wayne?s Tha Carter IV.

In honor of the most loyal tandem in hip-hop?s modern era, let?s rank all 17 of Drake and Lil? Wayne collaborations.

Project: Drake?s Comeback Season

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Lil? Wayne hopped on the final track on Drake?s second mixtape, if only for a half-ass verse that does a disservice to heat-check features he was putting out at the time. Considering Drake was 21 years-old, unsigned, and extremely raw, it could?ve been worse. Still, their first collaboration is easily their worst.

16. Stuntin? (2008)

Project: Lil? Wayne?s Dedication 3

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One year after linking up on Comeback Season?s ?Man of the Year?, Wayne, the best-rapper-alive at that point, gifted Drake an opportunity to show his potential with a guest spot on his highly-anticipated mixtape, Dedication 3. Drake didn?t disappoint, laying down a two-minute verse that displayed his growing star-power. Unfortunately, Wayne follows with an auto-tuned soaked verse that borders on cringeworthy. For their second collaboration, it?s obvious that Wayne didn?t find Drake worthy of his A-game.

15. With You (2010)

Project: Lil? Wayne?s I Am Not a Human Being

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Over a soulful beat that is reminiscent of Lil? Wayne?s mixtape output in the late 2000s, Weezy sounds polished while delivering three verses to the women in his life. While Drake contributes his angelic vocals to the hook, it?s far too short to come across as catchy. It feels like a Drake verse, if not a longer chorus, prevents the song from escaping mediocrity.

14. Family Feud (2017)

Project: Lil? Wayne?s Dedication 6

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Fittingly, Drake and Lil? Wayne reunite for their first collaboration (as a duo) since 2015, on a song whose title exemplifies exactly what Lil? Wayne?s been going through over the last few years, a la his back-and-forth battle with Young Money?s parent company, Cash Money. No matter, though. Drake starts off with a laid-back, catchy verse that touches on everything from Kaepernick, Jay-Z, and Meek Mill. If only Lil? Wayne had shown up on his verse.

13. Gonorrhea (2010)

Project: Lil? Wayne?s I Am Not a Human Being

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It may be an obnoxious beat, but back in 2010, it hardly mattered. Months before he would begin his prison sentence, Wayne released the last album while he was at his peak. ?Gonorrhea? wasn?t one of the album?s highlights, but it featured the double-time flow that Wayne was recognized for, along with a respectable verse from up-and-comer, Drizzy.

12. Unstoppable (2009)

Project: Drake?s So Far Gone

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Another song ruined by Lil? Wayne?s auto-tune obsession. It?s too bad. The beat was like nothing rappers were spitting over at the time. Drake impressed from the outset, bobbing and weaving around Santigold?s ?la la la la la la? during his first verse. Just as you excitedly waited for Wayne to lay the smack down, the sound of his auto-tune drawl makes you want to turn it off immediately. In his defense, he had nothing to prove back in 2009; his position atop the throne was unimpeachable.

11. She Will (2011)

Project: Lil? Wayne?s Tha Carter IV

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In early 2011, Lil? Wayne entered prison as the best rapper alive; when he came out, his protege (Drake) had undoubtedly usurped him as the alpha-dog in hip-hop. This made their first collaboration that much more anticipated. Although Drake?s sole contribution was the hook, it was good enough to carry the song in between exceptional Wayne verses. Two years prior, Wayne had said ?We gon? be alright if we put Drake on every hook?. ?She Will? solidified his claim.

10. Used To (2015)

Project: Drake?s If You?re Reading This It?s Too Late

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At the time ?Used To? dropped in early 2015, it?d been over three years since Lil? Wayne had appeared on a Drake project. The last time, on Take Care?s ?HYFR? and ?The Motto?, Drake was still trying to solidify his place atop hip-hop. By 2015, he had long become the alpha-dog. It was sobering to witness Drake wipe the floor with his mentor; on the other hand, it must?ve been rewarding for Lil? Wayne; watching like a proud big brother, as his protege took the rest of the rap game to school.

9. Grindin? (2014)

Project: Lil? Wayne?s Tha Carter V

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Three months after proving he wasn?t washed with ?Believe Me?, Lil? Wayne dropped what was assumed to be Tha Carter V?s second single. After carrying the first two verses, Wayne passed the baton to Drake. Amidst his career Apex, Wayne?s protege anchored the song just as he?d taught him.

7. Ignant Shit (2009)

Project: Drake?s So Far Gone

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Rumored to have already secured a record deal with Young Money, Drake released So Far Gone in early 2009; none other than the label-head, Lil? Wayne, appeared on four tracks. Over Jay-Z?s ?Ignorant Shit? beat, Drake holds his own, if not one-upping his idol, over the first two-and-a-half minutes. Lil? Wayne brings his full arsenal, anchoring the track with his own two-minute verse. Still, it feels like Wayne contributed nothing more than a leftover verse.

7. Ransom (2008)

Project: N/A

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On September 4, 2008, ?Ransom? broke the internet. On the heels of his magnum opus, Tha Carter III, Lil? Wayne was amidst a historic heat-check; teaming up with up-and-comer, Drake, was a statement. Unlike on their previous two collabs, Wayne emptied his clip. After Drake held his own over the first two verses, Wayne took the youngin? to school.

6. Successful (2009)

Project: Drake?s So Far Gone

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While ?Best I Ever Had? cemented Drake?s crossover potential, his follow-up single, ?Successful? solidified his ability as a rapper. The production is perfect, Trey Songz? hook glistens, and Drake contributes what was at the time, the two-best verses of his career. Five minutes later, Wayne enters, delivering his best verse on a Drake song to-date. In hindsight, it?s clear that, for the first time, the mentor was taking his protege very seriously.

5. Believe Me (2014)

Project: Lil? Wayne?s Tha Carter V

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Three years following Lil? Wayne?s release from prison, Young Money?s hierarcy had changed. Drake was undoubtedly the best-rapper alive; Wayne?s last four projects ? two albums and two mixtapes ? flopped. By the summer of 2014, hip-hop heads were forced to consider that Wayne was washed up. ?Believe Me? put that discussion on the back-burner. The fire-spitter hadn?t sounded this hungry, this, alive, since Tha Carter III.

4. Right Above It (2010)

Project: Lil? Wayne?s I Am Not a Human Being

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If I Am Not a Human Being was Lil? Wayne?s pre-prison curtain-call, then ?Right Above It? was the victory lap. Backed by triumphant production, Drake leads the track off with what was at the time, arguably the best guest spot of his career, before Wayne does cartwheels over the beat. It?s apex-Wayne; perhaps the last time that he?s sounded this confident, care-free, and genuinely happy. It?s not their best collaboration, but it is their most-inspiring.

3. HYFR (2011)

Project: Drake?s Take Care

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Lil? Wayne had his hands full with this one. Weeks after getting out of jail, he was forced to anchor what is perhaps Drake?s best verse of his career, not to mention tasked with handling hook-duty. Naturally, Weezy F Baby held his own. There were no signs of rust, as the former best-rapper-alive made it seem like he never left.

2. The Motto (2011)

Project: Drake?s Take Care

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It?s only been six years since Take Care was released, yet nothing feels more dated than ?The Motto?; not the song, no, rather, the motto, aka YOLO. That was a thing? I know, I know. I feel the same way. Still, the song is as undeniable as it was in 2011. The beat is catchier than anything on the radio today, Drake?s opening verses are addictive, and Lil? Wayne?s laid-back flow is the perfect curtain-call to the biggest hit they?ve been apart of.

1. Miss Me (2010)

Project: Drake?s Thank Me Later

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?Miss Me? tops this list because it?s the best that both MCs have sounded on a song together. It?s their best collaboration because it?s the most enjoyable, simply because they?ve never sounded more excited. Their shared exuberance makes it impossible not to picture them smiling during their verses, two rappers basking in newfound territory; Drake, amidst his rapid ascent toward hip-hop?s throne; Wayne, perched at the top, happy to let his protege in on the ride.

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