Listen Live
Desktop banner image
97.9 The Box Featured Video
The Great Debates Powered By Remy Week 1

Source: Avery Green / Radio One Digital

If you were to ask anyone who had two of the biggest “runs” in hip-hop in the last two decades without necessarily having a real hiatus – it is Drake and Lil Wayne.

Both in their own ways are legends. Both have all-time mixtapes, Drizzy with So Far Gone, Wayne with his unbelievable streak between the Sqad Up series, Dedication 1 & 2 as well as Da Drought 3. Both have mammoth albums and singles to their name, and they even had a co-headlining tour together appropriately titled, Drake vs. Lil Wayne.


The first in our Great Debate series tackles arguably the two biggest artists previously signed to Cash Money Records and two of the more consistent hitmakers of this current generation. Numbers can’t truly define the impact of Drake and Wayne, and that’s where you – the listener comes in.

All this week we’ll be celebrating both Drake and Wayne for Black Music Month, culminating in a head-to-head Star Wars mix on Good Morning H-Town at 7 AM on Friday, June 5th. They’re brothers, Drake considers Wayne a mentor, and Wayne considers Drake one of the best rappers in the world, period so this is a friendly matchup.

So for starters, we’re diving through the duo’s 38 listed collaborations since 2008 (17 of them strictly as a duo, which would make for a pretty good playlist) and picking out the best ones.

08. “I’m Goin’ In” feat. Jeezy

Technically this originated on a Jeezy mixtape in 2009, Trappin’ Ain’t Dead, but I’ll be damned if it isn’t an immediate riot starter by the time Wayne gives props to the Sigmas. Wayne’s time here is brief, and Drake’s verse became more popular over the years due to the “21 years I ain’t never met a good cop” line. In September 2009, it was added to the EP version of So Far Gone just to show that rap’s next big thing had arrived.

07. “Miss Me”

During 2010, all eyes were on Drake to hold on to the Cash Money ship while Wayne had to do a year behind bars over a 2007 gun charge in New York City. He ultimately succeeded with Thank Me Later, an album which promptly announced him even more to mainstream fans and spawned several chart-topping singles. “Miss Me” is one of the best collabs on the album with Wayne easily on full skate mode (“I got so many different styles, I am a group”) and Drake walking all over the in a full celebratory gloat.

06. “Family Feud”

Dedication 6 and D6: Reloaded are the third-best entries in Wayne’s Dedication series and for the first time since 2015, Drake and Wayne got to hop on a track together as a duo. “Family Feud” finds Wayne connecting bars and non-sequiturs as he did during his absolute peak from 2005 to 2010 at a dizzying pace and Drake’s far more secure in his stature as one of hip-hop’s go-to rappers. Plus, he openly used the track to dead his beef with Meek Mill and big up Colin Kaepernick.

Join Our Text Club To Get The Latest Music, Entertainment, Contests And Breaking News On Your Phone. Text BOX to 24042 to join!

05. “Right Above It”

The theme song from Ballers features the following: 1 Drake verse which plays homage to OutKast, Hollygrove and him slowly getting out of his 2010 feature pocket. You know the one, where “and uh….” became a calling card, 2 Wayne verses where he absolutely floats on the beat as if it were a victory lap before prison and 4 minutes where both of them sound as confident and relaxed as possible.

04. “Ignant Shit”

“And I’ll take probation, I don’t want that T.I. and Vick vacation.” If you were a Waynehead back in 2009, you understood quite well that if you gave Wayne a Jay-Z beat (see “Death of Autotune,” “Show Me What You Got,”) he was going to absolutely demolish it. One of the more prolific early offerings from the Drake/Wayne family tree and one of the many that firmly established that Drake was going to be here for a little while.

03. “Ransom”

During his manic recording peak, “Ransom” arrived at the height of Lil Wayne’s popularity. Tha Carter III cemented him as the most popular rapper in the world. Drake appearing on “Ransom” in 2008, a year after Comeback Season was an absolute show-and-prove moment for the then bubbling Toronto MC. And for two minutes, he absolutely did. And then … well, peak Wayne showed up to remind people who guested on 77 songs the year before and didn’t miss once.

02. “Believe Me”

In 2014, when Wayne was still shaking off post-prison rust, it was Drake who was on top. And when people were wondering what the sound would be from Tha Carter V, “Believe Me” was supposed to be the opening salvo and it firmly announced that Wayne indeed still had something to prove. In essence, it’s half the reason why we got Drake vs. Lil Wayne as a tour in the first place. Nothing felt bigger than knowing, “Oh, Wayne rapping rapping.”

01. “HYFR”

There are two Drake & Wayne collabs on Take Care, which is by and large believed to be the most celebrated Drake album. The biggest “hit” so to speak, is “The Motto,” which I can’t exactly qualify as a full-on Drake win even though its a full celebration for both Drake and Wayne. However, “HYFR” hits harder and coming off the fact that it was Wayne fresh off prison still finding a groove? Perfect execution.