In roughly the early 1900s, painting dissolved into abstraction and appropriation, and artists working since then have veered away from realism. As modern life splintered and proliferated, popular music rushed to catch up to the visual arts, first with the advances of jazz and then with those of its contemporary offspring, hip hop. While a stickler might argue that sampling, improvising, and making mixtapes (as opposed to more formal LPs) is more in the rhythm of modern life, OutKast doesn’t buy that.

OutKast have never culled “a little bit of this, a little bit of that.” From the lush studio instrumentation (first pioneered in Southern rap by their producers, Organized Noize) to the committed, heretical shamelessness of their beats, Andre 3000 and Big Boi have always explored music-making unapologetically, at the risk of radically revising their sound despite its positive reception. They stand always in direct opposition to the cooler, jazzier achievements of their peers on the East Coast, who rarely themselves sang, played an instrument, or spoke of emotional attachment in a deep, intelligent way.

And so they have come very far with a wild, unpopular model of producing music, so much so that certain OutKast fans only know an album or two well. Your cape-and-cane Aquemini aficionado might want to slow down the frenetic gun battle that is Stankonia. The Top 40-lovers who know exactly what you shake it like during “Hey Ya” often do not recognize the OutKast of “Player’s Ball” (It warranted a Sean Combs video in its day.) Ladies who lilt at Love Below pillow talk may visibly cringe at the interplanetary soundscapes of ATLiens.

A 2003 review characterized Atlanta as the “hip-hop id to New York’s ego.” Accordingly these transformations, rather than simply signaling conceptual turns in music-making, serve as foundations to OutKast’s understanding of what real love can be. Rap, particularly from the South, plays host to masculine bravado more often than not. R&B, on the other hand, celebrates seduction and the interplay between vulnerability and strength. As OutKast grew closer to uniting the two, their depictions of lovers changed from the “hos” mindlessly populating Southernplayalisticadillacmuzik to the emasculating, problematic bedmate of “Where Are My Panties?” on The Love Below. While particular genres might dramatize romance at the behest of an available mood, OutKast has grown and grown and grown beyond that, into a level of hardness that is actually quite sad: one that rejects the possibility of love, yet bows to every move of the opposite sex. Of the songs that aren’t just lyrical or dance floor victories, most grasp at dreams destroyed: not waiting for intimacy, but after it. Apologies, disavowals, partings, epiphanies, infidelities, and deviancies crowd OutKast’s lyrics.

Apparent even on Frank Ocean’s fresh “Pink Matter” remix, on which both Andre and Big Boi rap, they did not fall into the realization together. Though Big Boi has remained the more prolific of the two, it’s still clear that he did not absorb the sensuality — the heart — of Andre’s leaps forward on The Love Below and Idlewild.

For a super-close duo who have not reunited on a track of their own in seven years, the question is clear: “If what they say is, ‘Nothing is forever,’/ then what makes love the exception?” The brazen self-assurance of their music remained until their last real collaboration, 2006’s Idlewild. But in its sad, stuck, recurring harmonies, it had become what it remains in Big Boi’s work now: hard — not just any will, but the determination that gets you out of bed after a breakup, or on the dance floor without a date. That fierce, false insistence that alone, you are enough.

Considering the depth of OutKast’s catalog, cherrypicking 10 songs is something of a masochistic endeavor, mitigated only by the sheer pleasure of immersing oneself in all that amazing music in order to make such decisions with authority and confidence. Even then, we’re sure to disagree. So what follows is one longtime fan’s opinion. Let’s hear yours in the comments.

10. “N2U” (from Idlewild, 2006)

On an album that tastes overdone where the rest of OutKast bleeds rare (or at least medium-rare), “N2U” shines, and simply. There’s very little to say about it, which is in large part why it stands out. Though Idlewild, a quasi-soundtrack to the duo’s film of the same name, champions studio mastery at a level unexplored by the group, it splashes too happily through an ocean of studio sound effects, employing delectable drum samples, marching bands, and a symphony of special guests. It does not avoid borrowing from the sorts of old-timey music you might hear at a wedding, for example.

“N2U” is none of that. It’s got the naked brutality of R&B: palm-muted guitars, a chorus that — true to its sexuality — floats on just drums and bass, and a plethora of sex-hortations toward the bedroom. It flutters down with ’60s baroque pop harmonies reminiscent of the Beatles and then takes a quick dive to sultriness. OutKast is up to some of its funkiest, sexiest moves on “N2U,” all hushed and sassy; it becomes delightfully obvious they mean the preposition “into,” not the idiom.

9. “Decatur Psalm” (from ATLiens, 1996)

OutKast’s sophomore album takes them to another gangsta planet, where they sketch their native Atlanta as another world (ATL + aliens) where drug dealers and rappers cruise from dubbed-out locale to dubbed-out locale. Though much has been made of the racial undertones associated with alienhood, ATLiens sounds more immediately like a rumination on the South. Particularly with the era’s focus on rap from the East and West coasts, OutKast became one of the first groups to stridently attempt a Southern sound.

Andre and Big Boi have scattered fish and grits, Cadillacs, and East Point big-ups through all of their lyrics, and the production even in 1996 favored the crisp high registers, gun-like snare pops, and ubiquitous bass drum bumps that would defy the cool sparseness of New York hip-hop.

On “Decatur Psalm,” OutKast makes the mistake that most rap groups do at some point in their career, usually with supremely cheeseball results — they present a song that focuses on a fairly concrete narrative, rather than experimenting with themes that might stylistically sound good. Occasionally, however, the result can be wonderful and complex: the Beastie Boys’ “Paul Revere,” A Tribe Called Quest’s “I Left My Wallet In El Segundo,” and De La Soul’s “Jenifa Taught Me” all exceed the limitations of a storytelling structure, and “Decatur Psalm” doesn’t falter as it draws from gospel and the Commodores to evoke a Southern dirge.

The magic is in the conversations. Guests Cool Breeze and Big Gipp radio back and forth with Big Boi about a drug deal violently busted by the feds (Bill Clinton is hilariously “Bill Clampett,” it seems), but each rapper is careful to weave icons of Southernness throughout. They hide from the Red Dog Unit (a now disbanded paramilitary division of the Atlanta Police Department), buy a second Cadillac Fleetwood, and vow never to give in, “till that big girl from Decatur sing.”

OutKast and co. tell the story by overlapping sentences and rephrasing thoughts, which heightens the present-tense immediacy of the song. There’s an excellent move by Cool Breeze, who slyly lets the listener know he suspects wire-tapping as he apologizes for not returning his friend’s car while trying not reveal his location: “You tell his folks that I’m sorry bout that Lexus / I’m ’bout to dip and see my sister up in… naaah!”

8. “So Fresh, So Clean” (from Stankonia, 2000)

“So Fresh, So Clean” is about nothing. Not in the way that Seinfeld is about nothing (where in fact it’s about everything), but actually … nothing. So it falls into a rich tradition of rap music, in which the measure of a great rapper is whether they can rap about their great rapping, or about their great stuff. “So Fresh, So Clean” is decidedly the latter — free, easy, and begging to be blasted from car speakers. Big Boi’s verses juggle objects from “canary yellow ’79 Seville”s and “Monte Carlos” to “YKK” zippers and “gator belts” amidst a panoply of drugs and drinks. Conversely, the only proper nouns in Andre’s verse are “Anne Frank” and “Rick James”: perversity reigns as Andre proposes a freaky attic hideout to a female subject.

“So Fresh, So Clean,” which constitutes merely a synthesizer floating over a fat, staccato drum loop and bass line, proffers the neatest bed possible for creativity in of all OutKast’s work: nothing at all, none of the melodrama of Aquemini or ATLiens, stands between the fresh, clean rhyming on Stankonia and its audience. The raps are permitted to trip into and climb out of the crisp cracks within rhythms, and consequently we hang onto each.

7. “B.O.B.” (from Stankonia, 2000)

I started jogging not long ago.

I’ve hated it my whole life, absolutely hated it. Quit two sports teams (the same one, actually, two different years) because of it, and I still tense up seeing sweaty joggers on the street. But when you’re trying to beat stress, exercise for free, or quiet accumulated self-doubt, a couple million endorphins probably never hurt anyone.

When played too loudly, few songs get me off my ass like “B.O.B.” I remember no less than two weeks ago telling a friend I could hardly listen to it, with its goldfish-like attention to genre and totally absent un-politics (“Bombs Over Baghdad”?). But one day I was flagging on a run, doing my research (which often means listening to the same music in diverse circumstances), and feeling ready to “pull over.”

The skipping drum fills skittered onto the scene, Andre machine-gunning right along with a hand-programmed breakdown, and I looked into the face of a Hasidic man I passed, absolutely terrified. I ran a couple miles more than I thought I would, and after several repetitions of “B.O.B.” began to realize that the feeling that I could do anything was in no small part a sonic repercussion of the song’s spirit.

“B.O.B.” is an expansive, articulate middle finger to the structural and temporal expectations of rap music — way too fast and way too multifarious for any white-bread rapper to begin thinking about accompanying. Its words are rhythms more than signs, and the song nurtures wackiness and esotericism at a level simply unacceptable by modern standards. My submission to its singularity allowed me to enjoy its heart-in-head pounding and enter its totality, one which celebrates how far OutKast had (and has) come, and what it is capable of: “When you come to ATL, boy, you better not hide/ ’cause the Dungeon Family gon’ ride/ ha!”

And then there’s that bizarre outro: shouted over and over and over, and leaving us nowhere nearer decoding “PO-WER MU-SIC, electric revival! / PO-WER MU-SIC, electric revival!” but repeating it over and over all the same.

6. “Aquemini” (from Aquemini, 1998)

“Aquemini” is the eponymous album’s gorgeous deconstruction of personality versus reality. It grapples with rappers’ authenticity through the lens of dualities, constructing a portmanteau of Andre’s and Big Boi’s signs, Aquarius and Gemini.

Now, question: Is every nigga with dreads for the cause?
Is every nigga with golds for the fall? Naw
So don’t get caught up in appearance
It’s OutKast, Aquemini: another black experience

The duo addresses the profound questions here — Does the material culture make the rapper? Or the thinker? Do the trappings indicate otherwise? — in their own way throughout, both grounded in realism and jazz chords that drip with regretful hindsight. Where rappers in New York might have been waxing Five Percenter ideology or talking Back-to-Africa, Big Boi chastises irresponsible young rappers (“Let your paper stack instead of going into overkill/ Pay your fuckin’ beeper bill, bitch”) while Andre despondently warns, “Even the sun goes down/ heroes eventually die.”

Instead of the lyrical braggadocio of most rap in the ’90s, “Aquemini” employs parallelisms that illuminate real truths of rapping, in which both materialism and poetry can work together to make music. Music that confronts the reality of being a rapper, that insists that your actions and words can fill voids left open by a genre built on irreverent caricature.

5. “Roses” (from The Love Below, 2003)

Particularly when Andre writes a song, one can never know whether OutKast will handle a difficult subject indecorously. “Roses” could astound on sheer sneer alone, accompanying a piano-man R&B stomp with a sniveling rejoinder to a woman looking for a fat wallet, but it goes for the throat. Not only is the female subject not “down to Mars” enough for the guys, but she’s so money-obsessed, she can’t realize it.

Instead of pining for the possibility of genuine, uncomplicated attraction, OutKast draws attention to the failure of the girl’s priorities, and embarrassingly: “Roses” ends on about 40 seconds of variations on the word “bitch,” which will make just about any two people listening together uncomfortable. Where they could have drafted a more poetic repartee, it’s worth noting that the song’s hook rests on the observation that though she think’s she’s great, Caroline is not. Rendered childishly (“like poo-oo-oo!”), OutKast brilliantly follows form with function to prove that they are “down to Mars”: not fussy, but still out of this world.

4. “Spread” (from The Love Below, 2003)

Yes — you can combine Zombies-like organs, a drum-and-bass beat, and Latin-jazz piano to get something really, really sexy. Really, you can.

“Spread” enters a suite of tracks on the indomitable The Love Below (starting with “God” and arguably ending with “Roses”) that detail a character called the Love Hater’s encounter with a woman he meets while looking for sex. The song addresses their actual encounter from start to finish, not sparing a sound collage featuring a car driving, keys slamming down, and pants unzipping.

One cannot resist the sexual tension created by the beat’s immense disparity with the music, and the melody’s resolution during each chorus (unsurprisingly after the word “spread”) satisfies silkily. Andre possesses that unequivocal falsetto that communicates even to the lamest heterosexual male a uniquely charming, soulful, playful sexiness.

Even the most conscientious listener can’t help being taken in by that voice. When he raps, the level of intensity recalls that of being backed into a corner. As Andre implores his subject to, “Dance on the tip of my tongue/ Shake the clouds until there’s no more wetness in them,” I’m right there, unfortunately, fighting off the shivers.

3. “Unhappy” (from Speakerboxx, 2003)

Riding on a Southern beat that most resembles ’90s West Coast achievements vastly sped up, Big Boi mixes stilted blasts of rhyme with a deeply soulful synthesizer hook that occasionally (and so satisfyingly) reaches too-too high á la Mariah Carey.

The beat, a collaboration with the venerable Mr. DJ, slams unstoppably; the chords do not modulate at all, and they inspiringly propel the head-down/spirit-up insistence that, though “happiness came and went like Mom and Dad’s relationship… you might as well have fun / ’cause your happiness is done / when your goose is cooked.”

From Big Boi’s Speakerboxx, his contribution to their 2003 double album Speakerboxx/The Love Below, “Unhappy” has a propensity to constantly trip over itself but keep running, with Big Boi stumbling to spit out advice well before each verse begins, only allowing himself to relax when the warm chorus harmonies wash over the song. His subject matter, though, is far from unfocused: we see his parents’ debt, exposed by the brilliantly funny epiphany that “Santa Claus was / nothing more than Vanilli,” and an alcoholism driven by an unhappy home (held at a distance, as a movie: “graphic language, mild violence, / and the silence of the fams”).

“Unhappy” itself pushes us to move forward, but is itself fairly bleak; Big Boi only slows down while rhyming to offer the consolation that, despite the troubled upbringing, at least “we got that hot sauce!”

2. “Ain’t No Thang” (from Southernplayalisticadillacmuzik, 1994)

You have to love a song about hyperviolence that samples Miles Davis. And not just any Miles, but a pretty rare funk ballad off of Live Evil, featuring one of the weirdest and most perversely experimental ensembles of Miles’s career.

For a writer, few faculties can prepare you to write about rap with neither rap slang nor academia at your fingertips. But I’ll say this: nothing mystifies more people at a party than putting on “Ain’t No Thang.” That bizarre horn squeal that lines each verse, that speaker-rotting sub-bass, that lyrical experimentation in which each verse is a Rubik’s Cube of possible solutions — and that endlessly repeatable chorus (“It’s all about that cess’ in your chest/ It’s the joint!”). Yes, it’s a song about riding around Atlanta with a lot of weapons and then smoking a ton of pot, but it’s also a sonic pleasure drone.

For someone as prone to constant analysis as I am, “Ain’t No Thang” is one of the few songs that resonates deep desires for bodily, exuberant music and makes me shut up. By the end, I’m shamelessly squawking, “… but a chicken waaaang!”

1. “Hey Ya!” (from The Love Below, 2003)

Andre’s contributions to the double album Speakerboxxx/The Love Below crush any and all expectations of love songs. But it’s the awful epiphany of loneliness during “Hey Ya!” that thrusts The Love Below onto a pedestal. How masterful must one be to have written a danceable chart-topper (with every mark of triumphant girl-getting) that actually documents a lost faith in love and the acquisition of unashamed coldness?

Where he starts the song knowing “My baby don’t mess around/ because she loves me so,” Andre guides us through the spiraling realization that the couple is, “in denial/ when we know we’re not happy here,” even thanking his still-together parents for at least proving love can exist somewhere. “Hey Ya!” proceeds methodically — without a single drum fill or extraneous synthesizer note — from the recognition that his love has faded to myriad dance breakdowns and shout choruses, squawking away.

Eventually, bewildering notions like “separate’s always better/ when there’s feelings involved” and all the beautiful sensitivity of “Where Are My Panties?” and “Prototype” disappear in the wake of frantic appeals to be “cooler than cool ICE COLD!” and “on y’all baddest behavior.” It’s sad, but so simultaneously joyful. For OutKast, the only way out of emotional emptiness seems to be the “Hey Ya!” way, flattening any remembrance of awkwardness past by going psychotic on the dance floor.