An Honest but Unsuccessful Argument in the Case For: André 3000 Being the Greatest Rapper of All-Time

Image by: Sterling Monksgard

Guest spots are one of Hip-hop’s most defining acts of diplomacy. As a featured artist you’re expected to be dope and justify the fee commanded for your appearance. But not too dope. Nobody wants to get murdered on their own shit. However, you also need to set the pace. If you’re getting on a track with someone of a similar level of skill, then you’re going to need to feed off of each other a little bit, right? Give them no choice but to go back and write that verse again. Shit, go rewrite yours if they come out swinging. Also no subliminals; even something that could be misinterpreted as a subliminal. Getting murdered on your own shit is one thing, but someone taking shots at you while hiding in plain sight is something else entirely. If you can get two artists together that can understand these unspoken rules of the game then usually the feature is all the better for it. There’s a chemistry in the booth, the verses compliment each other. Its works. It’s Hip-hop.

Like with any set of rules there’s always a notable exception; an anomaly in the process that all do accept and comply with. For guest spots that anomaly is Andre 3000. A 3 Stacks guest spot only really needs to be one thing: itself. It transcends subject matter, beat selection and even genres. Rick Ross willingly handed him centre stage on “Sixteen.” Frank Ocean switched the whole vibe of the track up in between those “Pink Matter” verses, and just the mention of his name via adlib, has us fantasising over a verse that doesn’t even exist on Kanye’s “30 hours.” There’s really nobody else in Hip-hop that has cultivated that kind of mythical platform for themselves when they feature on somebody else’s record. Ever. Think about it. Who has ever really had it exactly like that? And if nobody else has ever really had it exactly like that, then does that mean that Andre 3000 is in fact the greatest rapper of all-time? Let’s explore.

It should go without saying that any GOAT qualifying criteria does not purely come down to guest spot notoriety. So let’s begin our exploration by taking a look at 3 Stack’s own material. Outkast have two classic records. Maybe three. And certainly nothing in their discography that’s anything less than a four out of five effort. But again, GOAT qualifying criteria cannot and should not be attributed to albums and even if it was, two classic records probably wouldn’t cut it. Plus none of these are solo albums, but we’ll get to that later. So let’s continue our analysis by setting a criteria and assessing on each part:

1.Pound for pound over 16 bars

There’s obviously a lot of stiff competition here. The great verse writers are plentiful and their highlights stand out even more when looking at their best work. Mos Def maybe has a case for best verse off all time on Black Star’s “Thieves in the Night,” and is a consistently strong performer even if his entire discography doesn’t always resonate with everybody. Go back to some of those Canibus verses from the late 90s — it’s hard to imagine anybody operating at a higher level. Jay-Z, Nas, Rakim, Tupac, Biggie, Chuck D, maybe even Eminem if we consolidate his best work from 99–02, they all warrant consideration along with others. There’s also a broad range of lyrical content from these great verses which perhaps carries more weight depending on your tastes. Are we going for social commentary, introspectiveness, battle raps, hustlers ambitions, best guest features? Where Andre 3000 stands out here is that he probably has a lot of these bases covered without being an outright winner in every single category. You could make an argument for greatest verse of all time on “Rosa Parks,” he’s even murdered R’n’B singers on their own shit. Maybe he doesn’t have a Jay-Z quotable that’s you could use on your instagram bio, but the lyrical complexity and playfulness of his best verses stand side by side with anybody.

2.Subject versatility

Synthetic technology, alien life, the club, playalistic lifestyles, how to dress well, the apocalypse. Is there anybody else that can glide over these subjects better? There’s an authenticity in the delivery that allows him to talk about ecological issues with the same precision and attention to detail as getting laid. Outkast were making us dance, but whispering the truth in our ears while we moved our feet.


Outkast released their first single “Player’s Ball” in the Autumn of 1993. This was pre Covid. It was also pre Spotify, pre Napster, and pre coastal feuds. 21 Savage was in diapers and Bill Clinton had just started his first term as President of the United States. Andre Benjamin is an old head no doubt, but he is an old head that is embraced in a different kind of way by Hip-hop’s new generation. He’s not on tracks with Kid Kudi, Travis Scott, Frank Ocean or Anderson Paak as a way to pay homage to a bygone era. Instead the psychedelic, Afrofuturistic funk that Outkast had simmering in a 90s Atlanta dungeon, resonates more than ever with this generation who all came up off of that sound and fused it with their own. Lyricism may arguably not be as much a focus in a lot of Hip-hop now, but sonically I think its fair to say as a genre it takes more risks. Coastal sounds are increasingly a thing of the past, and a more electronic leftfield style of production has set in. Andre 3000 pioneered a lot of that 25 years ago, even down to the dress code.


Yeah that’s not even a debate. Go listen, seriously just go listen.

5.Album quality

So this is where it gets tricky and even more subjective than an already subjective debate ordinarily would be. Outkast have two classic albums, maybe three. Andre 3000 however does not have a solo album to his name. Sure, you can count The Love below if you want, but it’s still an Outkast album, and he’s not even really rapping on it. It’s a little weird, maddening even that we do not have one earnest Andre 3000 solo album that we can use as a yardstick for how the above mentioned skills would play out in longform. The fact that we don’t have one undoubtedly adds to his legend, but it also counts against him in a big way. It’s not just the absence of any, but what it suggests about an ambivalence to rap he’s had over the last decade or so. Last year when the late great Kobe Bryant was asked how good Shaquille O’Neal could have been if he had a work ethic that matched his own; Kobe stated quite confidently that Shaquille O’Neal would have been the greatest player of all-time. Shaq, despite not being able to resist clapping back a little bit, took it for the playful jibe wrapped within a compliment wrapped within a jibe, that symbolised their legendary relationship. Kobe was right though. Shaq was blessed with the God given ability to be the greatest basketball player of all-time, but didn’t want it on the same level as others. Not a knock, just a fact.

There’s a comparative argument to be made here with Andre 3000. Again, this is not a knock; I’m not suggesting that 3 Stacks didn’t work his tail off throughout his career, just like Shaq. It’s just that the focus and priorities may have just been a little different. A little less obsessive. Andre 3000, by his own admission, felt by 2017 that rap was a “hobby” and something he was becoming too old for at age 42. People got upset over that. I got upset over that. But over time I’ve come to feel that it’s a position that we all have to respect. He’s not talking about Hip-hop as a genre, just himself. But the casual relationship with Hip-hop that he’s had for over a decade cannot be ignored. No matter your natural talent and how easy you can make something look, you can’t really be the best at something unless you’re a maniac for it too. Like Kobe, like MJ. Jay-Z doesn’t need to release albums anymore, and already “retired” before Outkast released their last record. But he still does make albums, pretty consistently. It’s not even that he can’t leave the game alone because it needs him anymore, he needs the game. Not for the same reasons as 20 years ago, but because he truly seems to still love doing this. So really the strength in the case for Andre Benjamin falls apart right here. He simply hasn’t taken the kind of challenges within the genre required to stand on his own ahead of the competition. Standing on your own and making great rap albums is hard, just like being a finals MVP. Few have done it. Andre 3000 has taken the decision to make being a great rapper a chapter of his life, but not his whole life. And he will only remind us of his greatness when he chooses fit. He doesn’t have an interest in meeting the qualifying criteria, so leaves it up to us; his rabid fanbase to see if we can sneak him in on a technicality. But we can’t, we just can’t. We know the rules of the game, and so does he. He just doesn’t want to play.

Father, Husband, Storyteller, Jedi. In that order. Also Director at

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