In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.
Before they reached #1 on the Billboard Hot 100, Outkast had already released three full masterpieces. They’d helped bring Southern rap to the center of the world, and they’d given the first great soundbite on behalf of a whole new generation of regional rappers. They’d established a persona, and then they’d complicated and consciously undermined that persona. I would argue that Outkast had already become the greatest rap group in history. Your mileage may vary, but you can’t deny that Outkast had already etched their place in rap without ever pandering to crossover audiences. So when Outkast did suddenly surge their way to the top of the pop charts, it was a little disorienting for those of us who’d already been paying attention. It was like: Cool, but why now? Why this song?
But also: Why not? Disorientation was always a big part of Outkast’s whole appeal. They were the exception, the group that refused to be pigeonholed in any way. As teenagers, even as they adapted the Cadillac-pimping style that would help establish Atlanta’s rap identity in the minds of listeners, Outkast also subverted that style at every turn. Big Boi and André posed as laid-back gangsters, but they rapped dense thickets of words with rare levels of nuance and empathy and playfulness. As they grew, and as they moved in different aesthetic directions, those guys dropped their previous poses and tried on radically different ones, but they always seemed united in spirit and purpose. They made brilliant music, and they sold millions of records, but they never landed a single in the top 10 until that fourth album arrived. Maybe the world just needed time to catch up.
Or maybe the song itself was the thing that finally crossed Outkast over. In the context of Outkast’s discography, “Ms. Jackson” is a relatively low-key affair — one more slice-of-life drama, rendered through wordily heartfelt writing and hazily funky music. But in the context of the pop charts, “Ms. Jackson” was a true curveball. In the decade-plus before “Ms. Jackson,” the few rap records that topped the Hot 100 were the ones that most successfully aimed for crossover status — though sheer novelty, through party-ready catchiness, through immediate-bellringer samples, whatever. Outkast never played that game. They just made a slinky, memorable song about a real situation, and that song arrived at the exact right moment. Sometimes, that’s all it takes.
“Ms. Jackson” wasn’t Outkast’s only #1 hit, but it was the culmination of a long journey, and it might’ve also been the beginning of the end. We’ll get to the ending eventually, but before we get into all that, we need to talk about the beginning. February 1, 1975, it happened: Antwan André Patton was born in West Savannah, way before he started rapping. Four months later, André Lauren Benjamin was born in Atlanta. The two didn’t meet until 16 years later. (When Big Boi was born, Neil Sedaka’s “Laughter In The Rain” was the #1 song in America. For André, it was Earth, Wind & Fire’s “Shining Star.” One of those seems more appropriate than the other.) Antwan Patton spent his entire childhood in Savannah, but when he was in high school, he moved to Atlanta to live with his aunt, and he started attending Tri-Cities High, a local performing-arts school. That’s where he met André Benjamin.
They were almost the Misfits. At Tri-Cities High, Antwan Patton and André Benjamin impressed each other with their rap skills and their deep musical knowledge. Along with a few friends, they put a group together. Their friends dropped out one by one, but Big Boi and André stuck with it. At first, they called themselves Two Shades Deep. Then, another group of kids at the same school took the name Four Shades Deep. Here’s Big Boi, in Fred Bronson’s Billboard Book Of Number 1 Hits: “To keep from infringing on our own name, we looked in the dictionary. We found Misfits, but there was already somebody with that name, so it was Outkast.” In a world where Glenn Danzig decided to call his late-’70s New Jersey punk band Vincent Price And The Good-Time Ghouls or whatever, maybe Outkast really would be the Misfits.
Even as kids, Outkast had obvious talent. Pretty soon, the Atlanta production team Organized Noize got interested. Big Boi: “They taught us the ropes of production and how to make music and how to get your right tone together. We got into deep training, jogging around the block for a couple of miles, rapping, getting your breath right.” In 1992, the same year that they became a group, Big Boi and Dre made their on-record debut on Organized Noize’s remix of TLC’s “What About Your Friends.” That was also Organized Noize’s first production credit. (“What About Your Friends” peaked at #7. It’s an 8.)
Organized Noize worked out of a basement studio that they called the Dungeon, and a whole core of young rappers formed around them — a crew that would go down in history as the Dungeon Family. Outkast were the Dungeon Family’s obvious breakouts. The production team had a deal with LaFace Records, the Atlanta-based R&B label that TLC called home. Organized Noize wanted Outkast to sign with LaFace, but Babyface and LA Reid kept saying no. Big Boi: “They turned us down two times. They didn’t want to do rap music. Dr. Dre came out with The Chronic back then, and they were in awe of how many records he sold. LA thought about giving hip-hop a chance, and he gave us a shot.” This was a good decision on LA Reid’s part.
After signing with the label, Outkast recorded a song for the 1993 label compilation A Very LaFace Christmas. Their “Player’s Ball” was not, strictly speaking, a Christmas song. Instead, it was a celebratory jam about Southern Black life, with a euphoric falsetto hook from Organized Noize member Sleepy Brown. Only the sleigh bells in the beat had anything to do with Christmas. When “Player’s Ball” started to get some rap-radio airplay, someone at LaFace decided to release the song as a single, with the sleigh bells taken off of it. Sean “Puffy” Combs came down to Atlanta to direct the music video, and he might’ve changed André Benjamin’s life by convincing him to take off his shirt to film the shooting-pool scene. A new sex symbol was born.
“Player’s Ball” was an out-of-the-gate hit. It topped the Billboard rap chart and went #12 R&B. “Player’s Ball” also crossed over to the Hot 100, where it peaked at #37. The single went gold. In the spring of 1994, Outkast released their debut album Southernplayalisticadillacmuzik, a head-spinning work of lived-in funk. The album went platinum. At the Source Awards in 1995 — the same night when Suge Knight famously taunted Puffy and kicked off the storied East Coast/West Coast rivalry — Outkast won New Artist Of The Year (Group), beating out Bone Thugs-N-Harmony, Ill Al Skratch, and New York hometown heroes Smif-N-Wessun. The crowd, already getting into the whole coastal-rivalry thing, booed Outkast for the crime of not being from New York. A frustrated, defiant André Benjamin responded with a line that instantly became part of the whole origin myth for Outkast and for Southern rap in general: “The South got something to say, and that’s all I got to say!”
Southern rap had existed before Outkast, of course, and plenty of it had been successful. We’d had 2 Live Crew and the whole Miami bass wave. We’d had the Geto Boys and the whole Texan Rap-A-Lot Records wave. We’d had Arrested Development. We’d had Kris Kross. But Outkast were different. At the height of rap’s inter-coast tensions, Outkast and their friends had a whole expansive aesthetic — one that could compete with what was happening in New York and LA without attempting to imitate either of them. Outkast were into Das EFX’s slippery linguistic games and the giddy experimentation of the Native Tongues crew, and they were also into Miami bass. I’ve always thought that Outkast at least partially based their style on those of the brainy, fired-up youg California groups like the Pharcyde and Souls Of Mischief, but Outkast’s sound was swampy and organic enough to set them apart completely. They were game-changers long before they truly crashed the pop charts.
That swampy, organic sound got a name soon enough. In 1995, Outkast’s Dungeon Family comrades Goodie Mob released their debut album Soul Food, and it included a song called “Dirty South” — a phrase reportedly coined by Dungeon Fam affiliate Cool Breeze. (Goodie Mob’s highest-charting single, 1995’s “Cell Therapy,” peaked at #39. Cool Breeze’s highest-charting single, the great 1999 Dungeon Family posse cut “Watch For The Hook,” peaked at #73.) Before long, Dirty South had become the name of both a region and a sound. Outkast remained at the forefront, and they at least came close to the pop top 10 when “Elevators (Me & You),” the meditative and melancholy lead single from their 1996 sophomore album ATLiens, peaked at #12. Until “Ms. Jackson,” that was Outkast’s biggest Hot 100 hit.
Over their first three albums, Outkast continued to grow, both musically and philosophically. The contrast in styles between Big Boi and Dre, who eventually took to calling himself André 3000 to avoid confusion with all the other Dres out there, became greater. André was looser and more exploratory, given to musings about the nature of life. On the other side, Daddy Fat Sacks B-I-G B-O-I was the same motherfucker that put them knuckles to your eye. Critics liked to play up the yin-yang balance between the two rappers, but I think the contrast is a little overstated. André could still talk hard, and Big Boi could still get weird. But the two rappers definitely pushed each other, and it all led up to the 1999 release of their third LP Aquemini, which might be my favorite album of all time, in any genre.
All three of those Outkast masterpieces went at least platinum, and the group definitely mattered to anyone who cared about rap music, but Outkast had never really become a pop-chart force. “Rosa Parks,” the lead single from Aquemini, is a classic that I remember hearing out all the time, but it peaked at #55. (That single also led to a legal battle with the actual Rosa Parks, who evidently did not like hearing her name used in the context of a party song.) By the time of Aquemini, Outkast and the Dungeon Family were no longer leading the commercial charge for Southern rap, even though Organized Noize had produced TLC’s “Waterfalls.” Flashier crews like Master P’s No Limit empire had risen up. The Cash Money era was around the corner. Outkast weren’t really a part of that anymore. They were becoming something else.
As early as 1996’s ATLiens, Outkast began to produce for themselves. They’d learned from Organized Noize, quite possibly the best production crew in rap history, and they had ideas of their own. Outkast weren’t averse to sampling, but they liked to use tiny, discrete chops from other records rather than big, nostalgia-triggering chunks. Outkast would flesh those samples out with live instrumentation from Atlanta club musicians and sometimes also from André himself, who was starting to play guitar. After Aquemini, Big Boi and André got together with David “Mr. DJ” Sheats, their tour DJ, to form a new production crew called Earthtone III. The first track credited to Earthtone III was “Neck Uv Da Woods,” a song that Outkast and the No Limit rapper Mystikal made for the soundtrack of the 1999 movie The Wood. (This column will get into Mystikal’s whole sordid saga very soon.)
While working on their 2000 album Stankonia, Outkast bought an Atlanta studio that had previously been owned by former Number Ones artist Bobby Brown. They had renamed the studio Stankonia, and they had named their album after it. Outkast took their time finding their new sound. André was increasingly getting tired of rap, and he wanted to push the group’s sound in different directions even though he was arguably the best rapper in the world at the time. Big Boi felt differently. The divisions between André and Big Boi were getting more acute. Around that time, the two started touring in separate buses; André had quit smoking weed, and he didn’t want to be around all of Big Boi’s smoke. You can hear those divisions at work in the album, which can be fractured and chaotic at times. That’s what a lot of people like about it. Rolling Stone recently called Stankonia the second-best rap album of all time. I say it’s the fourth-best Outkast album. Still great, though.
When Stankonia came out, Outkast went to a midnight record-release signing at an Atlanta record store, and they noticed that there were a whole lot of white people in the line. This was new. Outkast had already been hugely popular, but they were attracting a different audience. Maybe that came from all the touring they did — opening for Lauryn Hill on her Miseducation tour, playing college campuses constantly. (The one time I saw Outkast, it was a free college-quad festival in Baltimore during the ATLiens era.) Maybe it was André’s increasing stylistic flamboyance, both musical and visual. Maybe it was the way Outkast, like their former tourmate Lauryn Hill before them, seemed to sit both inside and outside the rap discourse. In any case, it was clear that a breakthrough was coming. I thought the breakthrough would take a different form.
The first single from Stankonia was an absolute aural attack. “B.O.B. (Bombs Over Baghdad)” is a wild, frenetic depth charge of a song, a blaring physical freakout that left me literally dizzy the first time I heard it. It seemed to crystallize all of Outkast’s furious innovations in one track. André and Big Boi rapped at a thousand miles an hour over a fast, hammering beat that recalled both Miami bass and the way-out rave music that André was coming to love. (He usually named Photek as his favorite.) But “B.O.B.” also had a swampy sense of funk and a triumphant guitar solo. It sounded like everything and nothing at once. I thought “B.O.B.” was the future. I was wrong.
“B.O.B.” never actually charted on the Hot 100, a fact that I find personally offensive. Part of the reason was its release. LaFace put “B.O.B.” out as a DVD single, packaging its wildly colorful video alongside the clip for the relatively sedate second single “Ms. Jackson.” Since “Ms. Jackson” got more radio play, that’s the one that charted. Today, though, “Ms. Jackson” has nearly 10 times as many Spotify streams as “B.O.B.,” so I guess I have to accept the idea that people just like “Ms. Jackson” more. “Ms. Jackson” is, to be clear, a great song; it’s just not the song that makes me feel like my soul is getting an electric shock.
“Ms. Jackson” started out with André 3000 writing at home, on an acoustic guitar. He wrote from experience. Three years before the release of Stankonia, André had become a father. André spent a few years in a relationship with Erykah Badu, and their son Seven Benjamin was born in 1997. (Erykah Badu’s highest-charting single, 2000’s “Bag Lady,” peaked at #6. It’s a 10.) Two years after Seven’s birth, André and Erykah broke up. They stayed tight, and Erykah guested on the Stankonia track “Humble Mumble,” but the situation was confusing and painful enough to inspire “Ms. Jackson.”
The Ms. Jackson of “Ms. Jackson” isn’t actually named Ms. Jackson. She’s Erykah Badu’s mother. In a rap radio interview years later, Erykah talked about her own reaction to “Ms. Jackson”: “I felt, at the time, a sore spot. I didn’t wanna hear that, especially when I heard Big Boi’s verse. When I heard André’s verse, I felt very good because his verse was really, really inspiring… He just told how he felt, and it was his honest feelings. I’ve always respected that and listened to it and appreciated it. So I liked it. But how did my mama feel? Aw baby, she bought up ‘Ms. Jackson’ license plates. She had the mug, she had the ink pen, she had the headband, everything.”
On “Ms. Jackson,” André and Big Boi have a sort of good cop/bad cop dynamic. The song’s chorus is a literal apology from André. On his verse, André tries to explain how two people might break up even after bringing a child into the world: “You can plan a pretty picnic, but you can’t predict the weather.” There’s something charmingly courtly about the flowery, halting way that André delivers his verse: “Asking what happened to the feeling that her and me had/ I pray so much about it, need some kneepads/ It happened for a reason, one can’t be mad.” André line about “forever — forever ever? — for-ever ever” is almost a secondary hook, the most quotable line from the song, and it’s about bonds dissolving. Through that sadness, André remains warm and calm and reassuring. Big Boi is another story.
Big Boi had a couple of kids by the time “Ms. Jackson” came out — one with the woman who he would later marry and another from a previous relationship. Big Boi’s relationships have never been as public as André and Erykah Badu, and I don’t know if he’s ever spoken about what went into his parts from “Ms. Jackson” — whether he was describing his own experiences or whether he was simply imagining a scenario. Whatever the case, Big Boi’s two “Ms. Jackson” verses come from a place of hurt and resentment. His narrator is extremely pissed off at his ex’s mother: “Let her know her grandchild is a baby and not a paycheck.” He talks about the grandmother sending neighborhood boys to go beat him up, and he threatens to “disconnect the cable, turn the lights out.” He warns that his lawyers are ready for a custody battle.
On “Ms. Jackson,” Big Boi sounds like a guy whose feelings have been critically wounded. It’s there in his delivery, a fast and purposeful snarl that contrasts sharply with André’s searching softness. It’s there in his words, too: “She never got a chance to hear my side of the story; we was divided/ She had fish fries, cookouts for my child’s birthday, I ain’t invited.” Like André, Big Boi promises to be there in the kid’s life, but he makes his pledges from an argumentative standpoint. He also tells his ex, “You and your girl ain’t speaking no more cause my dick all in her mouth,” which is not a nice thing to say. Big Boi finishes up by adding that his ex can go and get the hell on — her and her mama. It’s almost like Big Boi handles all the ugliness of the situation intentionally, freeing André up to be placid and thoughtful.
Musically, “Ms. Jackson” shows just one side of what Outkast were doing at time time. It’s a thick, heady song with a ton of melody. There are all sorts of warped little musical details — the drum sounds played backwards, the hazy organ, the softly clanging pianos. The track doesn’t boggle my mind, the way some Outkast instrumentals do, but it’s definitely pretty. Mostly, I think the music is there to stay out of the way, to emphasize the words and the sentiment on display. But André’s singsong chorus is a real hook, and I definitely spent months with it stuck in my head.
The “Ms. Jackson” video definitely helped. Director F. Gary Gray, who’d already made Friday and Set It Off and The Negotiator, didn’t try to literalize the “Ms. Jackson” storyline, which was a wise choice. Instead, Gray shows Big Boi and André unsuccessfully attempting to waterproof a backwoods tin-roof shack before a torrential rainstorm arrives. They look glamorous in a homespun way; all of André’s clothes appear to be knitted. And they’re surrounded by adorable animals — dogs, cats, an owl — who are all nodding along to the beat of the song. I don’t know how they got that effect, but I’m hoping they just waved treats in front of the animals’ faces in time with the tempo.
“Ms. Jackson” was the right song at the right time for Outkast. Stankonia eventually went quintuple platinum. For the next single, Outkast released the slinky Organized Noize production “So Fresh, So Clean,” which sounded musically closer to what they’d done on previous albums, and the single peaked at #30. Later in 2001, Outkast released a greatest-hits collection — they already had the catalog for it — and they got to #19 with the new single “The Whole World.” That song had a way-out off-kilter Earthtone III beat and an on-fire guest-verse from Big Boi’s new protege Killer Mike, who’d only just made his debut on the Stankonia track “Snappin’ & Trappin’.” (Killer Mike’s highest-charting single as lead artist, 2003’s “A.D.I.D.A.S.,” peaked at #60.)
Stankonia is the sound of an all-time great duo audibly fraying, moving in different directions. Soon enough, Big Boi and André 3000 would truly go their separate ways, though they found a way to keep the Outkast name going for a while longer. You probably already know that we’ll see Outkast in this column again.
GRADE: 9/10
BONUS BEATS: “Ms. Jackson” entered itself into rap’s linguistic lexicon quickly. Later in 2001, the former Lost Boys member Mr. Cheeks released the hit “Lights, Camera, Action!,” which used the line “I’m sorry, Ms. Jackson” as a crucial part of its hook. Here’s the “Lights, Camera, Action!” video:
(“Lights, Camera, Action!” is Mr. Cheeks’ highest-charting single, and it peaked at #14.)
BONUS BONUS BEATS: André 3000’s “forever-ever” line has been quoted about a million times in about a million contexts. Here, for instance, is Chris Rock quoting that line in a riff on marital cunnilingus during his 2004 special Never Scared:
And here’s Kanye West quoting the line on his 2005 single “Diamonds From Sierra Leone”:
(“Diamonds From Sierra Leone” peaked at #43. Kanye West will eventually appear in this column.)
BONUS BONUS BONUS BEATS: Here’s Jadakiss and Styles P using the “Ms. Jackson” beat to go after 50 Cent on a 2006 mixtape track:
(Jadakiss’ highest-charting single as lead artist, the 2004 Anthony Hamilton collab “Why?,” peaked at #11. As lead artist, Styles P’s highest-charting single is 2002’s “Good Times,” which peaked at #22. Jada and Styles both guested on Jennifer Lopez’s 2002 single “Jenny From The Block,” which peaked at #3. It’s a 7. 50 Cent will eventually appear in this column.)
BONUS BONUS BONUS BONUS BEATS: Here’s DJ Khaled’s video for his 2019 SZA collab “Just Us,” which is built completely from a “Ms. Jackson” sample:
(“Just Us” peaked at #43. SZA’s highest-charting single as lead artist, 2021’s “I Hate U,” peaked at #7. It’s a 7. She also guested on Doja Cat’s 2021 track “Kiss Me More,” which peaked at #3. It’s a 6. DJ Khaled will eventually appear in this column.)
BONUS BONUS BONUS BONUS BONUS BEATS: Here’s one of the greatest tweets of all time:
The Number Ones: Twenty Chart-Topping Hits That Reveal The History Of Pop Music is out 11/15 via Hachette Books. You can pre-order it here.
