The first name that teenaged André Benjamin and Antwan Patton settled on for their rap group was 2 Shades Deep, a fine name except that there was another crew in Atlanta that went by 4 Shades Deep, and even if there was no copyright involved, there was a rule against biting. The second name the two chose was Misfits. In that case, there was a copyright involved, and if André and Antwan had never heard of Glenn & Co., they knew it was best to stay away. But they identified with the sentiment behind the name: “We didn’t want to be compared to anybody,” Antwan says in Roni Sarig’s 2007 book about Southern hip-hop, The Third Coast. “We wanted our name to mean ‘apart from the norm.’” So they pulled out a thesaurus, found a word similar to “misfits” and made a slight tweak to the spelling, and just like that Outkast was born.
That moment came nearly 30 years ago, when the artists who would become André 3000 and Big Boi were just a pair of wide-eyed Atlanta teenagers in love with the music of De La Soul and Das EFX, hoping to impress producers Organized Noize and Laface Records label head L.A. Reid. A lot has changed since then: They recorded four classic albums—each more adventurous than the last—and sold 10 million copies of their fifth. They won over critics, both white and Black alike, and won a handful of Grammys. They gave Southern hip-hop a battle cry, and they gave East Coast purists a Southern group to latch onto. They went to the underground, and then to outer space, and then back to Atlanta. One started dressing differently. The other started breeding pit bulls. And together they changed the sound of popular music in the process.
On Saturday, Outkast’s seminal fourth, Stankonia, turns 20. It’s not their best album (that’s Aquemini) and it’s not the one that made them household names your mom would recognize (that’s the one with “Hey Ya!”), but it is their most daring, influential effort. You can read about the album’s legacy—and how it planted the seeds for the group’s dissolution—elsewhere on The Ringer today. Here, we want to celebrate the best songs in the Outkast discography (yes, we even accounted for the solo songs recorded for Speakerboxxx/The Love Below). Fifty of them to be exact. It includes all the hits and classics you’ve come to love, plus the deep album cuts and B-sides that show off their versatility. (And in one extraordinary case, it includes a Dre and Big Boi guest spot that’s too iconic not to account for.) Through it all, a theme emerges: André and Big Boi may have been one of the most popular and respected hip-hop groups of all time, but they achieved those things their own way. True to their name, they were outcasts, even if they gave the world no choice but to embrace them. —Justin Sayles
50. “Gangsta Shit” (Stankonia, 2000)
The best Outkast songs sound like how I imagine their weekends look. There were bigger songs like that on Stankonia, like “So Fresh, So Clean,” “B.O.B.,” and “Ms. Jackson”—I wasn’t 10 years old when the album came out, but can clearly recall football pads paired with vaquero chaps, Sleepy Brown in a fur coat, and nodding house pets. “Gangsta Shit,” buried 20 songs into the album, isn’t as flashy or iconic, but is just as adventurous, managing to do that Stankonia thing where it’s incredibly busy with diverse sound—guitars, drums, synths, whinier synths, layered vocals—but not claustrophobic. So crazy that it works. —Micah Peters
49. “Myintrotoletuknow” (Southernplayalisticadillacmuzik, 1994)
As the first real song off the first Outkast album—and one with the word intro in the title—“Myintrotoletuknow” is worth dissecting to see what Big Boi and André were trying to tell us. And what jumps out immediately is their paranoia about the present: “Time and time again see I be thinking about that future,” Big Boi opens the first verse; “Time is slipping, slowly but surely,” Dre opens his. They were just 19 years old, fresh out of high school and just beginning their recording career. They should’ve been excited, perhaps a little boastful. Instead, they were already wary, eager to get to the next stage. Looking back, it seems obvious that the most forward-thinking rap group of all time would’ve been focused on the future since their inception. But when they called their shot in 1994, they didn’t know what that future held, just that they needed to get there. —Sayles
48. “Wheelz of Steel” (ATLiens, 1996)
Like many other Outkast songs, the indisputable grooviness of “Wheelz of Steel”—which emanates from the Focus III–sampled beat, infectious hook, and unfaltering flows—can easily engulf Big Boi and André’s wisdom. One moment I’m nodding my head and listening to Big Boi tell a short story about how he’ll never get caught lacking again, then all of sudden André 3000 is running through walls in my brain like the Juggernaut talking about cod liver oil and the Illuminati. But there isn’t even the slightest sign of turbulence as the two trade verses. And just as my brain starts to fry from André opening my third eye, the hook and scratches courtesy of Mr. DJ come in and my feet start moving as my mind goes numb again. —Jonathan Kermah
47. “13th Floor / Growing Old” (ATLiens, 1996)
ATLiens is an album about a group on the rise, and “13th Floor/Growing Old,” the album’s final track, shows the responsibility that comes with ascent. Dre speaks on the group’s mortality while Big Boi criticizes hip-hop’s growing infatuation with capitalism. “I’m speaking ’bout you playing with that phony stuff you sharing,” the latter raps. “In your raps Mercedes-Benz and all your riches.” In total, it’s the exclamation point on an album that put the rest of the world on notice that this group and this region had a voice in music, all the while explaining that it comes at an emotional cost. —Logan Murdock
46. “The Whole World” (Big Boi & Dre Present … Outkast, 2001)
There’s a satisfyingly ~*~sPoOkY~*~ vibe to this song, which came out as a previously unreleased track on the 2001 greatest hits album Big Boi & Dre Present … Outkast. The vocals in its chorus sound like a choir of friendly ghosts. Its hook could easily work in tinkling MIDI form in a subterranean level of an Addams Family Game Boy game. André 3000 wears Dia de los Muertos face paint in the music video, while Killer Mike steals the show (Randy Moss–style) with his verse.
And yet the song’s message is somehow even darker and more existential than all of these details let on. It characterizes the extractive relationship between artist and audience in kinda horror-film terms. Can’t you just imagine a Blumhouse poster with the words “The whole world loves it when you sing the blues” and no further context haunting the rest of your day? Apologies if it already is. —Katie Baker
45. “The Rooster” (Speakerboxxx/The Love Below, 2003)
The Speakerboxxx appreciator has logged on. You can view Outkast’s second-to-last album as the beginning of the breakup of one of the most brilliant duos of all time—or as the start of Big Boi’s exceptional solo career. On “The Rooster,” Big Boi talks about a different uncoupling—the end of marriage—and doesn’t sound quite ready to go solo with regard to parenting. He shines, rapping over a million horns, and gets to do it for just about a whole album. —Rodger Sherman
44. “Mainstream” (ATLiens, 1996)
Outkast achieved enormous acclaim during the mid-1990s with their debut, Southernplayalisticadillacmuzik. But as ATLiens’ “Mainstream” suggests, “everything ain’t always peaches and cream,” especially when one is on the ascent. The T-Mo-and–Khujo-assisted track’s title is a play on words about the struggles of fame and the dope game. To understand the subject matter is to understand Outkast in 1996. They were coming off a successful album, and they had the fame. But they also had the burden of carrying a region not yet primed to run music and the reputation that they’ve ascended past their childhood peers back home. “Mainstream” pushes back on the notion, showing that no matter how far Dre and Big Boi get, they’re still two dudes from the A. —Murdock
43. “Snappin’ & Trappin’” (Stankonia, 2000)
For a long time, Killer Mike was hard to pin down. He was a little crunk, a little Memphis, a little Ludacris: he had all these phases. But Stankonia located his knack for hefty, hateful broadsides over dark, squirrely beats. I know Killer Mike and El-P met in the early 2010s, but, essentially, Run the Jewels begins with “Snappin and Trappin’.” —Justin Charity
42. “Bowtie” (Speakerboxxx/The Love Below, 2003)
In 1996, Outkast was just two dope boys in a Cadillac. Somewhere along the line, André pursued other forms of transportation, but in this preposterously funky song off of Speakerboxxx, Big Boi asserts that we can still call him the gangsta mack in a Cadillac. On “Bowtie,” Big Boi identifies himself as Lucious Left Foot and collaborates with Sleepy Brown, who’s credited as a featured artist for the first time after years of providing some of Outkast’s more iconic hooks. Antwan is smooth as a baby’s bottom rapping—and briefly singing—about putting on (and taking off) clothes culled from a variety of species of dead animals. As it turns out, he’s got a slightly different vision of seduction than the one André sings about on The Love Below. —Sherman
41. “Slump” (Aquemini, 1998)
From the opening baby wail it’s pretty clear that this song is about grinding. If “West Savannah” is Big Boi’s firstborn, dedicated to his roots “way before” he “started rapping,” “Slump” is his second child, written in honor of the hustle he knows all too well. With two features from Dungeon Family kin Backbone and Cool Breeze, the track is a reformulation of the age-old southern work song. The chorus is a pseudo-sequel to Southernplayalisticadillacmuzik’s “Hootie Hoo,” this time delivered over a faith-infused harmony of background vocals. “I’m strictly stressin’ dirty dirty,” Backbone chants, “Gon’ represent it to the T-top / Born and bred up on the street top / Get to the money and the sweet spot / And forever hollerin’ ‘Hootie Hoo!’ when we see cops.” With 3 Stacks taking this track off, Big Boi lives up to his main billing, fluttering up and down the beat with the dexterity of a hummingbird. “Cops and robbers, niggas be bound to get them dollars and cents,” he sermonizes, “They get in a slump like baseball players when they short on they rent.” Even if “Slump” recognizes that the game is rigged, it reminds listeners that some folks still have to play it. —Lex Pryor
40. “War” (Speakerboxxx/The Love Below, 2003)
If you want me to add your song to my playlist of saved jawns, throw in a beat change-up. It’s like watching a switch hitter slug a HR from each side of the plate, if done effectively. It’s surprising and not in the oh-shit-that-ghost-popped-out-of-that-lady’s-soul kind of way. “War” begins with a call to action from Big Boi on the general state of affairs in America. Then Screechy Peach interrupts to remind us that something beyond our control will imminently blow up right in our unassuming faces. It’s only a matter of time. And finally, boom goes the injustice. The media has shucked and jived, politicians are modern-day magicians, and war is always followed by horror and sorrow. When the beat changes, so does Big Boi’s sense of urgency. All he wants is for the population to smell the damn Folgers, and never forget that when Antwan André Patton brings food for thought to the table, you eat! —Keith Fujimoto
39. “We Luv Deez Hoes” (Stankonia, 2000)
One of the funniest things that happens in a rap song is when the rapping ceases to be athletic, or spirited, and just begins to sound … kind of angry, like a scolding. “We Luv Deez Hoez” is an embarrassing song that aged poorly, but I laugh every time I get to the end of Big Boi’s first verse:
Yeah, I told y’all niggas
About god damn takin’ them hoez to the Cheesecake Factory
Lettin’ them hoez order strawberry lemonade and popcorn shrimps
They ain’t goin’ do nuthin’
But try to take all your motherfuckin’ cheese! (Yeah!)
Partly because it’s fun to imagine a story involving Cheesecake Factory and strawberry lemonade that could work Big Boi up this much, but also because this is one of the few Outkast songs that André isn’t on pre-Speakerboxx, which, in some small way, means that he couldn’t avow it. —Peters
38. “Ain’t No Thang” (Southernplayalisticadillacmuzik, 1994)
Coming hard out of the Dungeon of Organized Noize, the 1994 track “Ain’t No Thang” is a statement piece. That statement: Tuck it in, everyone else—Outkast is here. Because of everything from The Love Below to “Lucious Left Foot” to André 3000’s Anita Baker clothing line, it’s sometimes hard to remember that Outkast was once just a couple of precocious teenagers navigating the streets of East Point, Georgia. “Ain’t No Thang” is now a reminder. Over an urgent, face-bashing beat—that screech was lifted from a few seconds buried in Miles Davis’s “Sivad”—both André and Big Boi go two-for-two on verses dripping in aggression, confidence, and wordplay. It’s gangsta rap for the South. It’s an arrival. It’s an announcement. Forget New York; forget L.A.; ATL won this day. —Andrew Gruttadaro
37. “Mighty O” (Idlewild, 2006)
If Idlewild—the musical film that birthed Outkast’s final-album soundtrack of the same name—was the group’s symbolic death, then “Mighty O” represents its defiant last gasp of air. Backed by a sample of Cab Calloway’s “Minnie the Moocher,” André and Big Boi came together for one last alchemic feat as a musical group.
Between 2006 and 2007, André was employing a scorched-earth policy, dominating on every rap verse he delivered. His appearances on UNK’s “Walk It Out,” Rich Boy’s “Throw Some D’s” and UGK’s “International Players Anthem (I Choose You)” were etched into legendary stone the minute they hit the airwaves. It was a decade removed from André’s prediction that the South would transform into a critical and commercial behemoth. And with the emergence of new competitors—Lil Wayne, T.I., Jeezy—André grew emboldened with the spirit of respectability politics and internal rhyme. At one point in “Mighty O,” he invites every person in the media to “a double diamond party in the North Pole,” which quickly becomes a tournament where everyone has to pretend to be André 3000. The catalyst for this antagonistic tournament, you ask? Well, 3000 was perturbed that no one liked his sartorial choices.
To Big Boi’s credit, he backs up his partner by comparing Outkast’s detractors to Rumpelstiltskin and then throws in a bar about a Dan Brown novel. In summation, the Atlanta group left the game as it had entered it—the best. —Charles Holmes
36. “She Lives in My Lap” (Speakerboxxx/The Love Below, 2003)
In 2003, The Love Below was the toast of critics. In 2020, it’s mainly remembered as a poor man’s Prince album with a few massive singles. But there are worthy tracks beyond “Roses” and “Hey Ya!”: “Prototype” is a perfect song about a wounded person rediscovering love; “Spread” is frighteningly sexy; “Take Off Your Cool” certainly plays like Grammy bait, but it sure sounds good. But the best moment on The Love Below is “She Lives in My Lap,” André’s answer to the Purple One’s “She’s Always in My Hair.” With Rosario Dawson riding shotgun, Dre unspools a messy tale of friends with benefits that have the potential for more. The beat matches the chaotic energy, with phantom snares and a haunting synth line that rattles in your head. Perhaps we should remember the album more for songs like this. —Sayles
35. “Babylon” (ATLiens, 1996)
I came into this world high as a bird from second-hand cocaine powder
I know it sounds absurd, I never tooted but it’s in my veins
While the rest of the country bungies off bridges without no snap back
And bitches they say they need that to shake they fannies in the ass clubs
André’s opening lines to “Babylon,” the key song in the introspective middle portion of 1996’s ATLiens, are arresting. In four lines, he paints a picture of the difference between choice vs. nature, drug tourism vs. growing up in that world. By the time of the album’s release, Dre had sworn off drugs and alcohol. So his verse on “Babylon” may come across as a tad preachy. But ultimately it came from a place of worry—for both society and, crucially, himself. —Sayles
34. “West Savannah” (Aquemini, 1998)
One of the cuts that didn’t make it on the Atlanta duo’s debut album, “West Savannah” was thrown onto Aquemini as a bonus, according to Big Boi in a 2010 oral history on the Southern rap classic. The four-minute track feels like you’re sitting backseat on a driving tour of West Savannah, Georgia, with Big Boi at the wheel and Sleepy Brown riding shotgun. A native of Savannah, Big Boi raps about growing up in his hometown, his family, and life in the streets of the Westside projects. The solo cut is a painting of Big Boi’s roots and origin story, and is one of dozens of examples of Outkast’s masterful storytelling. Fittingly, when the tour rolls to a stop, it transitions into another lesson on the “Da Art of Storytellin’ (Part I).” —Daniel Chin
33. “Da Art of Storytellin’ Pt. 2” (Aquemini, 1998)
It’s no wonder that the entries to this series of lyrical explorations would lead to moody edits on YouTube with animated action cartoons—“Da Art of Storytellin’” falls into a subcategory, along with “SpottieOttieDopaliscious,” of Outkast Songs That You Have to Read. Narrative journeys that frustratingly have no visual treatments: In “Part 2,” André and Big Boi follow the thread of a single, eerily prescient idea.
Imagine you woke up, looked out the window, and saw the sky falling. If you turned over, would the person you saw be someone you could truly spend the apocalypse with? Could you do it alone? —Peters
32. “Benz or Beamer” (New Jersey Drive, Vol. 1, 1995)
In this Southernplayalistic B-side that made its way onto the legendary New Jersey Drive soundtrack, Outkast momentarily betrayed their loyalty to Sevilles and El Dorados and declared, plainly, “Either want a Benz or a Beamer.” With a track that sounds this good, the fine folks at Cadillac likely had a hard time feeling hurt. —Sayles
31. “Hootie Hoo” (Southernplayalisticadillacmuzik, 1994)
Amid all the humid, luxuriant funk of Southernplayalisticadillacmuzik, what strikes you first about “Hootie Hoo” is how chilly and stark and ominous it is: a menacingly minimalist bass line, a pristine drum break from Black Sabbath’s “Behind the Wall of Sleep,” and a childlike falsetto chant (Hootie hoo!) that blows a fragrant puff of weed smoke into the room with every repetition. It’s simple, but extravagantly simple. “Tight like hallways / Smoked out always,” goes the refrain, and lyrically that’s all the song really needs. But André 3000’s vividly crass verse about Saturday-night hedonism and its consequences (“Now playing these bitches is my favorite sport / But ain’t no game when they be calling your name in the court”) is startling long before a girl calls him two weeks later with some unwelcome news, and his phone goes click, and the whole track, for just one breathtaking half second, goes silent. It’s the coldest moment on one of Outkast’s most gloriously frigid songs. —Rob Harvilla
30. “Humble Mumble” (Stankonia, 2000)
André’s verse on “Ms. Jackson,” the massive hit single from Stankonia, dealt with his relationship with Erykah Badu, the ex whom he had a son with. The verse is tender and acknowledges that sometimes love doesn’t work out. But nothing in it would’ve led you to believe that Badu would show up anywhere near the album. So it was shocking when she appeared as a guest—and on one of Stankonia’s best songs, nonetheless. “Humble Mumble” starts out serene and beautiful, a gentle African rhythm pulling at a beautiful soundscape, as André and Erykah share the chorus. And then, halfway through, the beat drops. It’s not an aggressive drop, but it’s explosive, immediately transforming the track from a head nodder to an ass shaker. But even with the bass and drums, the main attraction remains the former lovers, who were cool enough to set aside whatever drama there may have been for a special moment. (Bonus track: The two shared an equally as great collaboration in 2015 on Badu’s “Hello,” the sweet closer to her criminally overlooked But You Caint Use My Phone.) —Sayles
29. “Return of the ‘G’” (Aquemini, 1998)
This was a warning to all the punk motherfuckers: If you try to get a piece of mine, I gotta grab my piece. Self-defense is the only defense against the defamation of one’s self-expression from said punk motherfuckers. Thanks to the gossip, we got a return to Big Boi’s and Dre’s gangsta selves (and the masterful rhyming of time travelin’ with rhyme javelin). The instrumental is anthemic—kudos to the syrupy, orchestral vibes—laying the foundation for the duo to nullify any of the asinine side-eyes and shade they were getting from their haters/critics. On the hook, the word “gangsta” is drawn out like it was the group’s last-resort reminder to everyone that they were gonna relentlessly stick up for everything they worked tirelessly to have and, more importantly, for each other. There’s two things I learned from multiple listens of this track: Triggered 3000 is like the MJ “it became personal” meme, and Outkast is not Club Nouveau. —Fujimoto
28. “Jazzy Belle” (ATLiens, 1996)
“Jazzy Belle” is a bit of a deep cut off of Outkast’s sophomore effort, ATLiens, but it showcases André 3000 and Big Boi doing what they do best. Wordplaying the biblical queen Jezebel and “Southern belles,” the two trade bars about relationships and promiscuous women against a smooth beat with no need for any chorus. While the original Organized Noize–produced track more than holds its own, DJ Swift C’s remix—which features an assist from Babyface—is arguably even better. The song’s new hook and slowed-down beat gives it a more R&B feel, which is better fit for the radio. The remix was released as the final single for the album, and its extremely ’90s music video is still elite. —Chin
27. “Liberation” (Aquemini, 1998)
Aquemini’s penultimate track is preceded by “Nathaniel,” an interlude that features a real-life collect call that Atlanta rapper Supa Nate made to Big Boi from jail. Nate rapped a cappella over the phone, and Big Boi recorded his verse about life in jail and waiting to get out. The call perfectly introduces “Liberation,” a nearly nine-minute Dungeon Family gathering where André, Big Boi, Cee-Lo, Erykah Badu, and Big Rube take turns singing and speaking of freedom. With elements of jazz, blues, gospel, spoken word, and a somber grand piano behind them, each artist ruminates on what it means to be free. It’s a journey that touches on the anxieties that come from fame and success, family, religion, the music industry, and the Black experience. Over 20 years after it was released, the song’s lyrics and themes still resonate, and it remains a standout in Outkast’s extensive and stylistically diverse catalogue. —Chin
26. “Gasoline Dreams” (Stankonia, 2000)
“Gasoline Dreams” begins with two very important, albeit rhetorical, questions. André 3000 asks listeners, “Don’t everybody like the smell of gasoline?” before pivoting to a similar question about apple pie. By 2000, Outkast was as American as flammable liquids and fruit-filled pastry, but the group’s magnum opus, Stankonia, felt indebted to a creeping realization. Outkast’s fourth studio album unfolds like a bombastic awakening that the American dream is anything but, as the duo raps about cancer, AIDS, infidelity, and child support. Sonically, “Gasoline Dreams” is akin to the gates of hell opening as André’s yelp about losing balance converges with wailing guitars. Big Boi reminisces about receiving a key to Atlanta even as he’s still dealing with everything from the mundane (paying taxes) to the all too common (racial profiling). Sometimes when you reach the summit of popular music it gives you a better vantage point of what’s burning below. —Holmes
25. “The Way You Move” (Speakerboxxx/The Love Below, 2003)
Technically speaking, “The Way You Move” was still part of an Outkast project, given that it’s from the Speakerboxxx/The Love Below double album that the group released in 2003. BUT REALLY, “The Way You Move” was understood to be Big Boi’s debut as a solo artist, similar to how “Hey Ya” was understood to be André 3000’s debut as a solo artist, which also came from the same double album and had been released a month earlier. So there’s always that tricky history that you have to work your way through whenever you’re talking about this song. You have to know that in order to understand the biggest reason why this song is great, which is that it announced to everyone that if we really were headed toward an eventual dissolution of Outkast, which was a big rumor during this particular period of time, Big Boi, who’d largely been underestimated almost by default because of André 3000’s overpowering coolness, was going to be just fine. And more than that, Big Boi was going to shine. Which is what he does on “The Way You Move.” The rubbery charm of his voice is perfect in the spotlight, and revisiting this song now, it’s clear that he aimed to eventually make his own completely solo masterpiece album, a promise he fulfilled with 2010’s Sir Lucious Left Foot. —Shea Serrano
24. “Prototype” (Speakerboxxx/The Love Below, 2003)
Outkast had successfully integrated funk into hip-hop long before, but Speakerboxxx/The Love Below is the natural conclusion of those efforts, and “Prototype” is perhaps the best example of that end point. A slow-churning ballad driven by a gurgling bass line and André 3000’s deft touch, “Prototype” is a transportive jaunt that feels more than it sounds. (If that makes sense. Writing about Outkast is hard.) The lyrics’ hyperbolic yet grounded approach to love (“Let’s go to the movies”) is par for the course for André, but let’s be honest, you’re here for the vibes. And that’s what “Prototype” has in spades. I’m very stankful for that. —Gruttadaro
23. “Skew It on the Bar-B” (Aquemini, 1998)
As legendary Wu-Tang member Raekwon tells it, before this song no one in the East Coast was listening to any rappers from the South. But on “Skew It on the Bar-B,” the Chef definitely didn’t seem out of his element surrounded by some ATLiens. On the Organized Noize–produced beat, he flexes his prowess for moving weight, but it’s André’s bar warping that perks my ears every time: “I’m sorry, like Atari, who’s the cousin to Coleco / Vision? Caught a RICO, back on the street like Chico / DeBarge.” —Kermah
22. “Git Up, Git Out” (Southernplayalisticadillacmuzik, 1994)
What gets swallowed up in the shadow of their excellence is their age. Think about it. Southernplayalisticadillacmuzik drops in the fall of ’94 and Big and Dre are both a whopping ... 19 years old. So, surrounded by all the posturing bravado and wise-beyond-their-years street knowledge of their debut album, there’s “Git Up, Git Out,” sitting at track 12, fueled by angst, the most youthful of emotions. A baby-faced but already bald-headed CeeLo Green (part of fellow Dungeon Family crew Goodie Mob) delivers a blistering 29-bar window into the recesses of his mind, carefully pondering the difference between “high” and “too high.” Big Boi extols the virtues of maturation and manhood, while Big Gipp (another Goodie representative) plays the song’s resident working man, detailing his corner-boy morning routine. And then there’s André, dripping with righteous nihilism while pondering the value of his vote (“Ain’t nobody Black running but crackers, so, why I got to register?”). Each section of the track is brutally contemplative, equal parts angry and unsure. In combination, “Git Up, Git Out” strikes the balance between preachy and unbelievable. You could say the very same thing about the figures behind it. —Pryor
21. “Royal Flush” (Non-album single, 2008)
One of the great tragedies of 2000s hip-hop is that we never got a solo André record—or at least one where he was truly rapping. For a period that stretches roughly from 2007 to 2013, 3 Stacks blessed a long list of other artists’ records, twisting syllables and dropping gems in a way that surpassed even some of his best Outkast verses. There was, of course, his unimpeachable “Int’l Players Anthem” verse, but also his turns on the “Walk It Out” remix, and Drake’s “The Real Her,” and Jeezy’s “I Do,” and Rick Ross’s “Sixteen,” and, well, I could do this all day.
At the beginning of this run, Dre dropped the most surprising collab: “Royal Flush,” a reunion with Big Boi, featuring Wu-Tang’s Raekwon. The other two fought against the current of the track’s fidgety bass line and hi-hat. Dre, on the other hand, bends the track to his will, rhyming “car door” with “bottle” and ending on an extended metaphor that compares the hokey-pokey to the drug game—and you’re going to have to trust me on this, but it sounds amazing. The line that always sticks with me, however, comes in the front half of his 1:40-long verse: “It’s easier to run the street than walk in the sand.” For André, dropping a solo rap LP would’ve been the easy part. He chose to walk in the sand, and we all still followed. —Sayles
20. “Red Velvet” (Stankonia, 2000)
I’ve long assumed that there was some critical malfunction at the CD factory that resulted in hundreds of thousands of consumers receiving Stankonia copies without “Red Velvet,” which thus resulted in the perennial arguments about Big Boi being a second-rate rapper compared to André 3000. I can’t imagine listening to “Red Velvet” and nonetheless cultivating such weak-ass opinions. I’d be mortified. So, I assume it’s all a big misunderstanding. —Charity
19. “Crumblin’ Erb” (Southernplayalisticadillacmuzik, 1994)
God Bless Organized Noize kingpin Sleepy Brown, genius producer, songwriter, bald-headed style icon, and sweetly crooning hook machine, who turns this crucial Southernplayalisticadillacmuzik deep cut into the most serene and profound weed jam imaginable. “There’s only so much time left in this crazy world,” he purrs, doubled by slinky jazz guitar and sounding so laid-back he’s horizontal, he’s floating in midair upside down. “Crumblin’ Erb” is a song about street violence (Big Boi: “And drive-bys, kiss yo’ ass bye-bye, sayonara suckers / I flipped the script and turned the page, ain’t scared of you motherfuckers”) and the ideal way to reduce it (André 3000: “We is gonna smoke out until we choke out”). But Sleepy Brown’s stupendously chill chorus (love the whispered “It’s the master plan!”) is all you really need to know about both the problem and the solution. Even through the, uh, haze, the path to enlightenment has never been clearer. —Harvilla
18. “Chonkyfire” (Aquemini, 1998)
The final track to an iconic Outkast album that legitimizes their place in rap while showing a glimpse into their out-of-this-world future. As André 3000 aptly stated in this song,“You are now about entering the fifth dimension of ascension.” This song truly isn’t from this planet and it’s evident from the gritty guitar riffs that immediately hit your ear, and 3 Stacks’ intro:
“Woo, woo Yosky-wosky, peesky-weesky, What’cha wanna do-ski?”
Outkast makes it clear that what you’re hearing is alien-like, and that sound would extend to their critically acclaimed follow-up album, Stankonia. “Chonkyfire” is timeless—not just for its production, which has been sampled by both Eminem and Kid Cudi, but because of the statement it makes. The hook is basically saying that just like the Pied Piper, Outkast’s music brought people out of their hiding places, taking off the masks and allowing them to be their true selves. Outkast is nothing like what you’ve ever heard and the fact that they ended the song with their speech from the infamous ’95 Source Awards proves that they really had something to say. —Sean Yoo
17. “Two Dope Boyz (In a Cadillac)” (ATLiens, 1996)
An efficiently entertaining master class from two of the dopest MCs ever. The song begins by sampling the robotic line from the intro of “D.E.E.P.” off their first album, and what follows is a perfect back-and-forth from André 3000 and Big Boi. The production is loud and bright with a snare that hits deep within your soul. Outkast thrives when the juxtaposition of Big Boi and 3K is put on display and Two Dope Boyz does that perfectly in under three minutes. Within the hook, the line, “But in the middle we stay calm, we just drop bombs” references their treacherous surroundings, and how they sit in the middle and just write rhymes. That’s clearly evident in this track, and it also encompasses the trajectory of the rest of their immaculate career. —Yoo
16. “Morris Brown” (Idlewild, 2006)
Maximalism is, apparently, back, which means that maybe there’s still hope that “Morris Brown” will one day get the respect it deserves. This song, which was released on 2006’s bittersweet blowout Idlewild but had been originally produced years before that, is a sonic mosaic and an extended musical universe unto itself, even if it somehow never climbed above 95th on the Hot 100 and never made the rap charts at all.
It boasts an entire once-semi-famous collegiate marching band, thumping like the heart the lyrics describe; and guest vocals from Scar and Sleepy Brown; AND an appearance from Janelle Monáe in what was essentially her debut; A N D a music video that looks like a glorious, trippy amalgam of “Black Hole Sun,” “Don’t Come Around Here No More,” and Blue’s Clues. This song is, as they say, a lot—but then again, isn’t life? —Baker
15. “Hey Ya!” (Speakerboxxx/The Love Below, 2003)
G, C, D, E—the four chords that make up “Hey Ya!”; also the first four chords André 3000 learned to play on guitar.
“Hey Ya!” is an anomaly. Almost two decades after its release, it still barely makes sense—an upbeat, acoustic guitar-led, ’60s-evoking pop song made by one half of an iconic rap duo from Atlanta, about freaking divorce. Undeniably catchy, cleverly subversive, and unexpectedly profound, it asks what keeps people together—and it also asks “all Beyoncés and Lucy Lius” to get on the floor. It confirms that the only thing cooler than being cool is ICE COLD. It reinvigorates interest in the Polaroid camera. It builds a stage on which André plays eight different Beatles-like musicians. It gets in your head and your bones and never leaves.
Is it somewhat of a stomach-churning injustice that Outkast’s most well-known song barely resembles the rest of their catalog, let alone their best work? Probably. But at the same time, all of the things that make Outkast great—stunning creativity, the rejection of genre boundaries, and a unique knack for careful, perceptive thinking—are present in “Hey Ya!” So shake it. —Gruttadaro
14. “Aquemini” (Aquemini, 1998)
“The South got something to say”: in retrospect, André’s speech at the 1995 Source Awards in Manhattan pits Outkast against New York. “New York–wannabe-ism,” Killer Mike recalls. But let’s not forget the other regional coup: Outkast making better Dr. Dre albums than Dr. Dre could manage after The Chronic. “The hardest shit since MC Ren,” André notes. Musically, Aquemini draws so much life force from so many different galaxies. On the titular single, Big Boi explicates the album and, for that matter, the group: “We prayed together through hard times, swung hard when it was fitting / But now we tapping the brakes from all them corners that we be bending.” —Charity
13. “GhettoMusick” (Speakerboxxx/The Love Below, 2003)
If Outkast’s chief goal was to differentiate themselves from the rest of hip-hop, then “GhettoMusick” is something of a manifesto. The song is a tour de force of instrumentation, soul, and lyrics. From André’s chorus to the Patti LaBelle sample, the track serves as a grand introduction to the group’s most ambitious projects, the double solo album Speakerboxxx/The Love Below. Over a four-minute stretch, Big Boi sets the André-produced beat ablaze. It was another prime example that the group that never followed the rules invented some new ones themselves. —Murdock
12. “Roses” (Speakerboxxx/The Love Below, 2003)
Absolutely stupendous karaoke song. The insidious robo-funk bounce. The joyous call-and-response chant of Caroline! The silly sing-along profundity of that chorus. (“Roses really smell like poo-poo-ooh!”) And especially the meter-smashing way André 3000 barrels through the second verse: “I hope she’s speedin’ on the way to the club tryna hurry up to get to a baller or singer or somebody like that and try to put on her makeup in the mirror and crash, crash, craaaaaash into a ditch.” Harsh. Stupendous. “Roses” is a crucial bridge between Speakerboxxx and The Love Below (it marks Big Boi’s only appearance on the latter), and a top-10 hit despite its flagrant weirdness and, well, harshness: If you do pull it out at karaoke, just be advised that the outro requires you to repeat the words crazy bitch, like, 500 times. —Harvilla
11. “So Fresh, So Clean” (Stankonia, 2000)
The quintessential pre-party anthem. The jam you play just before you put on your sauciest fit before the function. The vibes are laid down by Sleepy Brown on the chorus and enhanced by Big Boi and 3 Stacks. The song—Stankonia’s third and final single—was the brainchild of Organized Noize’s Rico Wade, who came up with the iconic melody while in the shower one evening. The following day, he had Sleepy lay down the vocals, which are an interpolation of Joe Simon’s “Before the Night Is Over.” Surprisingly, André didn’t want to do the song initially but decided to after hearing Big Boi’s first two verses. As a result, the track becomes a competition between the two wordsmiths, with Big Boi using his southern game to lick his SpottieOttieDopaliscious angel like a lizard at the Honeycomb Hideout and André using his Funkadelic aura to prove to his queen that “the boy next door’s a freak.” The result is one of the best tracks in music and the soundtrack to the beginning of a great night. —Murdock
10. “Player’s Ball” (Southernplayalisticadillacmuzik, 1994)
Last February, just before his 78th birthday, George Clinton talked about adaptability as the trick to timelessness. When he was touring One Nation Under a Groove with Funkadelic, they’d reached the brink of exhaustion, having created so many spectacles on the road night after night with Dr. Funkenstein and his great, futuristic Mothership. When their single “One Nation” hit, rather than create a new mythology around it, the group leaned into the theme of accessibility, buying the stock of Army-Navy outlets to fill their wardrobe as they went out on what he called the “Anti-Tour,” creating fashion along the way. First the price point of fatigues went up in the surplus stores, and then you started to see the same silhouettes in big department stores, according to Clinton.
Outkast are often written about as the inheritors of Clinton’s particular spirit of subversion, and of his talent for timelessness, for obvious reasons. Their debut single, for instance, was supposed to be a Christmas song, and was made at least in part out of frustration. Having a nascent pseudo-gangster rap duo guest on a Christmas compilation, in the ’90s, no less, was their label’s idea of cross-promotion. How were they gonna get any respect? And yet, if you weren’t to watch the video—if you were to watch the video—that factoid would be pretty easy to forget. They too leaned into accessibility: It’s like a dream sequence, where a spindly André and a noticeably young-in-the-face Big Boi can have all of their friends together for a well-dressed, multi-course feast because they’re all alive, not just because it’s Christmas. They too created fashion along the way: I still want that Braves jersey, and I don’t even watch baseball like that.
Shit, let me get the faux-fur Kangol, too. —Peters
9. “Da Art of Storytellin’ Pt. 1” (Aquemini, 1998)
There is something immensely haunting about “Da Art of Storytellin’ (Part 1)”—the synth that croons in the background like the opening to a sci-fi anthology series, the patter of bongos that rattles off every few seconds. The track is exactly what it claims to be: an exhibition in the art of storytelling. Big Boi leads with the ballad of a woman named Suzy Skrew. (“They called her ‘Suzy Skrew’ because she screwed a lot.”) The two have a brief sexual escapade that ends with him giving her “a Lil’ Wil CD, and a fuckin’ poster.” The story is crass, his behavior is admittedly dickish. He gets what he wants because he wanted it. End of transaction. It’s just a story after all. Where Big shows us a snapshot of a day in his world, Dre takes us on a trip through someone else’s. “Sasha Thumper,” a childhood crush, who just wanted to be “alive,” but of course, life got in the way. He spins a tale about their connection, her life, how he used to hope she would appear at one of their concerts. But then the hook comes: Sasha died behind a school “with a needle in her arm, baby two months due.” Maybe there’s a lesson. Maybe there’s not. It’s just a story after all. —Pryor
8. “Rosa Parks” (Aquemini, 1998)
Big Boi and André 3000 open the video for “Rosa Parks,” the first single from their brilliant third album, Aquemini, by telling you exactly what they’re about to give you. Big Boi opens the talks, calling for very earth-bound groundwork. André agrees, then adds that they also need “some space, futuristic-type” things, barking that people (or, more specifically, rap in general) is “scared of that.” To which Big Boi responds, “All right then, let’s do both of them.” And then that’s exactly what the fuck they do. The song feels both familiar and cosmic, and it fucking rules. And it’s fucking unstoppable. And it’s fucking perfect. And the whole thing—calling their shot beforehand and then nailing it exactly correctly reminds me a lot of the stories about Michael Jordan telling defenders what he was going to do before he’d do it and still they had no answer for it, no way to stop it, no way to fully prepare for it, because he was Michael Jordan and nobody else was. —Serrano
7. “Elevators (Me & You)” (ATLiens, 1996)
André 3000’s concluding verse on the deep-space eerie and unforgettable first single to 1996’s ATLiens is one of best moments in Outkast’s whole catalog: He’s cornered by a starry-eyed old classmate at the mall and bluntly but deftly sketches out how far the group’s already come (“Elevators” reached a then-record-high no. 12 on the Billboard Hot 100) and how far they had left to go (the no. 1 hits would come later). “True, I’ve got more fans than the average man,” he concedes, “But not enough loot to last me / To the end of the week / I live by the beat / Like you live check-to-check / If it don’t move your feet / Then I don’t eat / So we like neck-to-neck.” The double-time burst is thrilling, and the mixture of hubris and humility is enthralling, and it’s all delivered with enough whirlwind charisma that everyone knew, even before those no. 1 hits arrived, that these guys would never go hungry again. —Harvilla
6. “Int’l Players Anthem” (UGK’s Underground Kingz, 2007)
Technically, this song isn’t eligible to be included on this list, since it’s not an Outkast release, instead coming out on a UGK album. But Outkast was no island—peninsula, maybe—and their connection with another perfectly paired Southern duo was too iconic to leave off. “Int’l Players Anthem” is just about the end of the line for both duos: Outkast would release only two more songs together (the great loosie “Royal Flush” and an unceremonious track on a DJ Drama compilation album) and UGK’s Pimp C would die several months after the song’s 2007 release. It serves as a crystallization of both groups at their best: four one-of-a-kind men rapping about the wildly different ways they love women. Each rapper glitters individually, but they become more fascinating when juxtaposed with each other. It’s fitting, considering the song itself is an ode to getting down with the team for those who have been rolling solo. —Sherman
5. “Ms. Jackson” (Stankonia, 2000)
“I apologize a trillion times,” concludes the pop-supernova chorus to Outkast’s first no. 1 hit, but what makes “Ms. Jackson” so thrilling is how agitated and wounded and combative that apology can be. Inspired in part by André’s fraught romance with Erykah Badu (and his consequently chilly relationship with her mother), the bulletproof Stankonia smash swings wildly from his wistful vulnerability (“Forever? For-ever-ever? For-ever-ever?”) to Big Boi’s brash defiance, echoing one of Badu’s biggest hits in his climactic verse that hits like a ton of bricks (“You keep on singin’ the same song / Let bygones be bygones, and you can go on and get the hell on / You and your mama”) even if you’ve heard this song a trillion times. Let it be known that Badu says her mother absolutely loved it: “How did my mama feel? Baby, she bought herself a ‘Ms. Jackson’ license plate. She had the mug, she had the ink pen, she had the headband, everything. That’s who loved it.” Let it also be known that it inspired one of the best tweets of all time.
I'm sorry Ms. Jackson (Oooooo)/ I am four eels/ Never meant to make your daughter cry/ I am several fish and not a guy— joshh O))) (@JNalv) February 20, 2013
4. “Southernplayalisticadillacmuzik” (Southernplayalisticadillacmuzik, 1994)
A thing that has been lost during all of this Outkast talk is how deliberate and intentional the group always seemed to be, even in their earliest days, which is the surest sign of their genius. Because think on it like this: Of course their first album was going to have a title (Southernplayalisticadillacmuzik) that only they could get away with. (It’s one of those titles where you see it and you say to yourself, “OK, that’s silly,” but then you turn the album on and you hear it and you go, “All right, actually it’s perfect.”) And of course they’d have a song on that album with the same name, and that song would be lush and soulful and contemporary in a way that felt like throwing the ball to where a receiver was going and not where he was standing. And of course they’d eventually release it as a single, except they’d make sure to not make it the first single, because that’s what everybody else would’ve done, and Outkast is not everybody else. Because they’re Outkast. They’re motherfucking Outkast. —Serrano
3. “ATLiens” (ATLiens, 1996)
So much of Outkast’s mythos, from the namesake of the group to their sophomore album, is based in physical and more meta geography. “The ATL for Atlanta, and the aliens for our status as foreigners in the hip-hop game,” André told the Los Angeles Times in 1996. “Atlanta was one of the last places to get out of slavery, and so that striving and sense of struggle comes across immediately in our music.” Twenty-four years later, “ATLiens” feels like a rough blueprint of what would one day make Outkast’s hometown hip-hop’s creative epicenter. For nearly four minutes, the larger-than-life characteristics of André and Big Boi begin to form. André’s clear-eyed and sober manifestations clash with Big’s increasingly entertaining slick talk. One moment, Big Boi is comparing his rapping skills to a “polar bear’s toenails,” while André is pondering the future of the human race. The pitched-up and pinched vocals of the hook sound otherworldly as the duo curves a simple phrase like “Oh yeah” into “Oh-yea-yer.” For all of its laid-back energy, “ATLiens” is indebted to the rage of outsiders. —Holmes
2. “SpottieOttieDopaliscious” (Aquemini, 1998)
“SpottieOttieDopaliscious” is the clearest hint that Outkast hails from a state with excellent marching bands. Although, as far as I can tell, Outkast invented marching bands in the first place. I played three different saxophones and wrote arrangements from hip-hop radio in high school, so I’m speaking from experience here. Outkast makes its biggest, hottest melodies sound so effortless, so cool. —Charity
1. “B.O.B. (Bombs Over Baghdad)” (Stankonia, 2000)
By this point, you’re either nodding your head or shaking it, and truthfully, either reaction is completely justifiable. Outkast’s catalog contains multitudes—Stankonia’s Afrofuturism sounds nothing like Aquemini’s mystical Southern drawl, which sounds nothing like the space-age boom-bap of ATLiens or the Cadillac-trunk-rattling bass of their debut. You’re allowed your preference, and if you choose “Player’s Ball” or “SpottieOttieDopaliscious” as your platonic ideal of an Outkast song, you’re not wrong. In fact, there are some solid arguments against “B.O.B.” as the best ’Kast song: It lacks the finesse of much of their best work; it tries to do a lot; it’s not even close to their biggest hit; if you remove André and Big Boi’s vocals, it’s not even a rap song. It also briefly served as a war cry for the most unjust war this country has ever waged, in the same way that “Born in the U.S.A.” is an anthem at Republican rallies. Perhaps a song that leaves that much room for misinterpretation shouldn’t be in the running for the best song from one of the best rap groups of all time.
The argument for “B.O.B.” at no. 1, however, is a simple one: It’s proof of concept for the Outkast experience, the song Big Boi and André were building to from the moment they met as teenagers while both window-shopping outside of a Ralph Lauren store. Starting with Southernplayalisticadillacmuzik, when they presented themselves to the world as conscious pimps, the duo made clear they wanted to break the mold. Much has been said about Dre’s “The South Got Somethin’ to Say” moment at the 1995 Source Awards, but little attention is paid to the purple dashiki he wore as he issued his rebel yell. They were never typical cats, so it makes sense they would craft atypical songs.
The approach gained them a lot of fans; at times, it also lost them some. They would satirize this on an Aquemini sketch, when a former fan tells a record store owner, “At first they were some pimps, man, but then they some aliens, or some genies or some shit. … Man, whatever. I ain’t fuckin’ with that no mo’.” But even if they felt it, it didn’t deter them. If anything they doubled down, and that’s where “B.O.B.” comes in.
Big Boi remembers the first time he heard André messing around with the skeleton of the song. His partner called him into the studio and hit play on the sampler. “It’s like the room started glowing. I was like, ‘Man, what the fuck are you doing back here?’” The answer was André was charting a new course for both the group and 21st-century music. It’s hard to remember now how rigid genre divides were in the ’90s, and that’s because of Outkast. In no small part, it’s because Big Boi and André crafted a song that combined hip-hop, rock, gospel, and drum ‘n’ bass. “B.O.B.” is explosive; at 155 beats per minute, it’s faster than practically any rap song you’d ever heard to that point, and it feels even faster—a runaway freight train, except your conductors are either dressed like Jimi Hendrix or wearing Mitchell & Ness. It’s amazing this was birthed on a traditional digital sampler like the SP-1200, and not, say, the console of a space shuttle.
The song broke barriers and challenged what constituted hip-hop music. Sure, others had experimented with the form before, but never like this. Shortly after its release, rap and R&B became more adventurous, and soon pop followed. We talk about genreless music a lot today. My guess is we’d do a lot less of that without “B.O.B.” But beyond the experimentation, the influence, the glowing studio room of it all, “B.O.B.” is an excellent song. It’s pure adrenaline and maximalism. It’s ridiculous enough to include a full choir and goddamn guitar solo, but great enough to pull them off. It’s power music that thunder pounds like a million elephants. In short, it’s Outkast doing the absolute most, and we couldn’t ask for anything more. —Sayles