Some artists create discographies so beloved and cherished that picking one as the best of the lot can seem cruel and arbitrary, like separating a favorite child out of a brood. The collected work of OutKast inspires such a feeling – at least their first five albums do, before the duo flamed out spectacularly with their final one to date, the soundtrack to the 2006 movie Idlewild. That one aside, each one holds a special place.

For Stankonia, released on October 31, 2000, it was hearing Andre 3000’s and Big Boi in their prime. For that album, there was a kind of anticipation that hadn’t been present during their 1998 album Aquemini, despite the fact it won feverish praise in the hip-hop press and earned a perfect “five mic” rating from *The Source *magazine, it didn’t quite cross over to the pop charts.

OutKast finally achieved that breakthrough with “Ms. Jackson,” which topped the Billboard Hot 100 chart in February 2001. Its appeal seems to solely rest on Andre 3000’s quirky chorus, and how he shifted from a vocal that’s awkwardly offhand (“I’m sorry Miss Jackson. Woo! I am for real!”) into one that sounds like an attempt at Muppets burlesque. But it is his interplay with Big Boi that gives this track its real impact. The latter is an unrepentant rogue who raps, “Let bygones be bygones/You can go and get the hell on, you and your mama.” Meanwhile, Andre 3000 offers poetic apologies on why love went wrong. “You can paint a pretty picture but you can’t predict the weather,” he sings.

Andre 3000 reportedly based his “Ms. Jackson” verses on his failed romance with Erykah Badu, with whom he has a son. However, it’s also clear both members of OutKast used their personal experiences as single fathers to write a song that resonates with anyone who has survived a failed relationship. Andre 3000 and Badu are hardly estranged; Badu appears near the end of “Humble Mumble,” a song that also got attention for Andre 3000’s line “too Democratic, Republic f*ck it,” since Stankonia was released just as a contested 2000 presidential election drew to a close.

While “Ms. Jackson” was the radio single, “B.O.B.” (a.k.a. Bombs Over Baghdad) was the stunning first “buzz” single. Many critics interpreted it as OutKast’s response to then-hot electronic club sounds like drum ‘n’ bass and Detroit ghettotech, and there’s some merit to that, particularly in its digital drill tempo, over which Andre 3000 raps, “Like a million elephants, a silverback, orangutan/You can’t stop the train.”

There are also elements of booty bass, the bounce rhythm that had ruled Atlanta nightclubs for much of the decade, and then was in rapid decline as the slower, elbow-throwing sound of crunk took over. Then there is the marching band influence, which you can hear near the track’s end as Morris Brown’s gospel choir shouts out, “Power music, electric revival!” Morris Brown is part of Atlanta’s historically black college universities, or HBCU’s. As shown in the 2002 movie Drumline, flamboyant marching bands are part of modern Southern culture. Meanwhile, the hybrid sound of “B.O.B.” gets a second Stankonia airing on “?”.

This is the brilliance of OutKast: They take what is distinctly regional and make it accessible to everyone. They were our entry point into the cultural idiosyncrasies of Southern rap. Now that we know infinitely more about the subject – thanks in part to them, Southern rap has loomed in the mainstream for over a decade – a fresh listen to  Stankonia reveals unexpected layers. There is “Gangsta Sh*t”, which is set at the same sluggish, narcotic pace as the screwed-and-chopped mixes of DJ Screw. Atlanta is ATL, shawty. Cut is a metaphor for sex. And long before trap became an overused cliché, OutKast made “Snappin’ and Trappin’,” where Big Boi’s then-new protégé Killer Mike rapped, “Our shit don’t mix like yay and lukewarm water/Better make it hotter, splash with ice, and make it rock up.”

If there’s one track that continues to puzzle us, it’s “Toilet Tisha,” where Andre 3000 sings about a pregnant teenage girl who decides to self-abort and dies in the process. We’ve since debated whether or not the song is graphic horror meant to deliver a pro-life warning, which Big Boi seems to emphasize in the second verse. “She could not properly handle a blessing in which she thought to be an obstacle in her path to adulthood,” he sings. “Tisha done came to the crossroads, and now she got to choose.” The bizarre synthesized funk, produced by Earthtone III (the group alongside longtime collaborator Mr. DJ), only muddies the waters.

“Toilet Tisha,” as Jon Pareles of the New York Times wrote, may be the album’s “one real misfire.” It is disturbing, but maybe that’s the point. Stankonia is a psychedelic adventure that ends with the seven-minute “Stanklove,” where OutKast’s Dungeon Family crew croons the title over and over, evoking Funkadelic’s Maggot Brain in their nakedly erotic dirge. Maybe we didn’t understand all of it, but somehow we got it.