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.

The week of Thanksgiving 2007, T-Pain had four of the top 10 singles in America. Technically, none of those four songs were T-Pain songs. A few months after T-Pain topped the Billboard Hot 100 with his own “Buy U A Drank (Shawty Snappin’),” he’d become the hottest freelancer in all of pop music. Just about anyone could score a hit as long as they had the phrase “Feat. T-Pain” next to their song title. And if a song didn’t feature T-Pain, or at least some version of T-Pain’s sleek and energized robo-voice, that song probably wasn’t getting very far.

T-Pain’s imperial moment showed that things were shifting. Pop listeners had come to accept the way T-Pain used Auto-Tune as a stylistic affectation rather than a cover-up for out-of-tune singing. R&B was moving in a direction that was less showboaty, more clubby. The pulsing textures of European dance music were finally making inroads on the American pop charts, which would lead to a dramatic shift over the next few years. And T-Pain himself was a dominant voice. Even guesting on someone else’s track, T-Pain had a way of overwhelming the song, making it his own.

The week that T-Pain held down 40% of the top 10, Kanye West’s bright and fizzy “Good Life” reached its #7 peak. (It’s a 9.) The Houston pop-rapper Baby Bash’s Lil Jon-produced “Cyclone” was sitting at #8, a week after it reached its own #7 peak; the best moment of that song was T-Pain attempting to imitate the sound of an actual cyclone. (It’s a 7.) That same week, another song with a T-Pain hook broke into the top 10; it’ll appear in this column soon. And the #1 song in America was the one that T-Pain basically gifted to Chris Brown, the teenage heartthrob who was still a year and a half away from becoming a national disgrace.

Chris Brown needed a hit. Two years earlier, Brown had reached #1 with “Run It!,” his very first single. That song turned Brown into a sensation. His live sets drew a whole lot of screaming girls. His self-titled debut went double platinum, and it spun off more hits. Brown was starting to land acting jobs — a recurring part on The O.C., a supporting role in the steppers’-competition sports flick Stomp The Yard. He was also becoming a familiar tabloid face because he was dating Rihanna, who was well on her way to superstardom. But that kind of teenage-heartthrob fame can often be ephemeral, and early indications for Chris Brown’s second album were not good.

Chris Brown originally wanted to call his sophomore LP Graduation, since it was set to come out around his 18th birthday — the time that he would’ve graduated high school if he hadn’t dropped out to chase pop stardom. But Kanye West claimed that title, so Brown instead gave his album the title Exclusive, giving MTV the slightly incoherent explanation that the record was “exclusively for those that will support it.” Exclusive was supposed to come out in August of 2007, but that was before lead single “Wall To Wall” crashed and burned, peaking at #79. The kid needed a different strategy.

“Wall To Wall” was the sort of song that Chris Brown would’ve released in 2005. It was a junior-varsity Usher club track — mostly written by one of Usher’s key collaborators, with lyrics all about how Chris Brown couldn’t get away from all the ladies chasing after him. It had a profoundly silly big-budget video about dancing vampires. Pop music was shifting in slight, intangible ways, and Brown was behind the curve. “Kiss Kiss” was the reset.

“Kiss Kiss” is basically a T-Pain song. T-Pain himself is all over the track. He handles the intro, doing a funny radio-DJ spiel about how Chris Brown’s new song is the thing that’ll solve all the disbelieving caller’s romantic problems. T-Pain also sings backup throughout the track and adds a brief, energized rap verse. More importantly, though, Chris Brown sounds just like T-Pain throughout the track. It was as if T-Pain had rented his whole style out to Brown, and Brown wasn’t the only one.

If you look at the T-Pain tracks that were filling up the top 10 during that one week in November, all of them feature lead artists adapting T-Pain’s sound while performing alongside the man himself. Kanye West sing-raps through Auto-Tune on “Good Life,” and he’d soon do a whole lot more of that. Baby Bash sing-raps through Auto-Tune on “Cyclone.” On the song that’ll soon appear in this column, the lead-artist rapper doesn’t use conspicuous Auto-Tune, but he does add a certain melodic bounce to his flow. And on “Kiss Kiss,” Chris Brown sings through so much Auto-Tune that it’s sometimes hard to tell which voice belongs to Brown and which is T-Pain.

T-Pain produced “Kiss Kiss,” and he co-wrote the track with Chris Brown. At first, it was going to be a song about butts. The original chorus: “She’s chunky chunky/ She’s thick thick.” But Brown’s handlers thought that was a bit too adult for his fanbase, even if Brown himself had just turned 18. Brown told MTV, “At first, we was making it a little grown, but my manager shut it down… We gotta keep it PG-13 at least.” (The video still has a scene where Chris Brown helpfully points out a butt.) Brown and T-Pain changed “Kiss Kiss” into a song about all the girls fantasizing about him: “She want that lovey-dovey/ That kiss kiss/ In her mind, she fantasize ’bout gettin’ with me.”

Those lyrics are pretty awkward, but “Kiss Kiss” doesn’t sound as kid-friendly as it reads. Instead, T-Pain’s beat is a bright, fizzy take on Southern club-rap. The bass pulses, and little synth-hooks bounce energetically around the track. I like the “whoof” sound effect underneath the verses. While the hook is at least nominally romantic, the song mostly just gives Brown a chance to flex. Brown’s singing sounds a lot like rapping, and most of his lines are about being fly. He’s got paper, girl. The Lamborghini with the spider seats — you’ve never seen it. (I always wondered what a spider seat was. The answer, as far as I can tell, is that Chris Brown was so into Spider-Man that he had his car reupholstered so that the seats looked like Spider-Man’s costume.)

Plenty of Chris Brown’s lines on “Kiss Kiss” don’t even come close to working: “I’m the epitome of this demonstration, I got the remedy/ You feelin’ me, so why is you hatin’ on my anatomy?” It’s only impressive to use SAT if you have a total understanding of what those SAT words mean. “Kiss Kiss” has a heedless forward energy that reaches its peak when T-Pain comes in with the guest-verse. T-Pain’s lyrics are as ecstatically meaningless as anything else: “Shawty, let me holla at you! You so hot! Hot! Hot! Hot! You think I’d be hollerin’ if you not? Not? Not? Not?” But T-Pain turns that meaninglessness into a party.

“Kiss Kiss” is ultimately just a fun-but-forgettable piece of melodic pop-rap, but its timing was just right. There were many, many teenage girls who wanted to love a new Chris Brown track; “Wall To Wall” just hadn’t given them anything to work with. Brown’s whole style was simple but physical. He was more of a dancer than a singer, and “Kiss Kiss” let him sing like a dancer. The video gave him a chance to showcase what his dancing skills.

The “Kiss Kiss” video is no masterpiece, but it’s a whole lot more retable than the vampire-fantasy thing that he tried to do on “Wall To Wall.” Brown worked with “Run It!” director Erik White, who would later make the Bow Wow vehicle Lottery Ticket. The clip takes place at a bright, sunny high school, and it involves two different Chris Browns competing for the affections of a girl — the same gimmick that Avril Lavigne used in her “Girlfriend” video earlier that year. Brown plays the dual roles of a hopeless, Urkel-looking nerd and an asshole jock, and the nerd naturally gets the girl.

The whole storyline of the “Kiss Kiss” video doesn’t really click, since Chris Brown is a whole lot more convincing as the asshole jock than as the sympathetic nerd. But the video works a whole lot better as a showcase for Brown’s dancing, which is just ridiculous. The guy was always an athlete, and the sight of him backflipping across a school-bus roof is honestly impressive. T-Pain can’t dance like Chris Brown, but he’s got a silly, irrepressible energy, and the video comes to life a whole lot more whenever he’s onscreen. He’s onscreen a lot.

“Kiss Kiss” became the hit that Chris Brown needed — the song that established he’d last longer than one album. The week after Brown’s Exclusive album came out, “Kiss Kiss” ascended to #1, beating out all those other songs with T-Pain features. That album eventually went quadruple platinum, selling better than Brown’s debut or any of the albums that he’s since released. Brown followed “Kiss Kiss” with the fluffy Stargate-produced love song “With You,” and that single made it to #2. (It’s a 7.)

During that whole stretch, Chris Brown never got raunchier than he did on “Kiss Kiss.” He presented a clean, approachable image to the world, and that image worked for a while. While “With You” was still thriving on the charts, Brown duetted with the former American Idol winner Jordin Sparks on her love song “No Air,” and that song became another huge hit, peaking at #3. (It’s an 8.)

In 2008, Chris Brown was popular enough to do TV commercials. Wrigley hired Brown, his team, and Polow Da Don to come up with a new jingle for Doublemint gum. That jingle sounded just like an actual Chris Brown song, and Brown quickly released a version of the jingle that was a full Chris Brown song. “Forever” came out on a deluxe version of Exclusive, and it went all the way to #2. (It’s a 6.)

Chris Brown got all these big looks because he came off as a cute, talented kid. That image didn’t last. The night before the 2009 Grammys, Chris Brown and Rihanna went to Clive Davis’ pre-Grammy party. After the party, Rihanna found a text message from another woman on Brown’s phone, and she confronted him. Brown went into a rage, trying to push Rihanna out of the car and then repeatedly punching her in the face while driving. When she tried to call the police, he choked her and bit her fingers. When someone finally called 911, Brown fled the scene and turned himself in to police that evening.

In the aftermath of that assault, someone leaked a photo of a bloodied, battered Rihanna to the media, and the sight was shocking and horrific. It would have a huge impact on both Chris Brown and Rihanna’s careers. Rihanna will appear in this column with many more songs, including one that Chris Brown co-wrote. (It came out and hit #1 before the beating.) Chris Brown hasn’t been back to #1 since then, but his career has endured. In a strange and troubling way, that terrible moment might’ve extended Brown’s shelf life, giving him a bad-boy antihero power that he never would’ve had otherwise.

Chris Brown tried to keep going like nothing had happened. He was charged with assault, but a judge let him off with probation and community service. Later in 2009, he released his album Graffiti. It tanked, and none of its singles went top-10. But Brown followed that with a storm of music — three mixtapes over the next year — and kept his foothold at R&B radio with songs like “Deuces.” In 2011, Brown made it back into the top 10 when “Look At Me Now,” a dazzling fast-rap display with Busta Rhymes and Lil Wayne, peaked at #6. (It brings me no joy to report that “Look At Me Now” is a 10.)

If the beating of Rihanna was an isolated incident, that would be bad enough. But it wasn’t. Brown kept doing shitty, violent things. There was a bottle-throwing nightclub brawl with Drake, an artist who will appear in this column a lot of times. Tony Parker, the Spurs player, got broken glass stuck in his eye during that fight, and he needed surgery. Brown also got into a physical fight with Frank Ocean over a parking space. There was the hit-and-run in Los Angeles. There was the fight in DC with the fan who wanted a photo. There have been a lot of lawsuits, too. Brown has gone through rehab and been diagnosed with bipolar disorder, and he still comes off as an overwhelmingly unpleasant human being. Just last month, Brown went off on an Instagram tirade about the people who still bring up the Rihanna beating: “If y’all still hate me for a mistake I made as a 17-year-old, please kiss my whole entire ass.” (He was 19, but who’s counting?)

Chris Brown actively steered into the whole outlaw image during that whole stretch, flaunting his gang affiliation and carrying himself more and more like a rapper. Maybe that lent him some transgressive appeal. Maybe people really saw him as being embattled and sympathetic. In 2011, I moved to Virginia, not too far from Chris Brown’s hometown, and I noticed a lot of Team Breezy shirts out in the world. To his fanbase, Brown’s genuine human shittiness seemed to make him more appealing.

Chris Brown and Rihanna eventually got back together and dated for a while, and she pronounced him “a good man.” The hits kept coming, too. In 2012, Brown’s EDM tracks “Turn Up The Music” and “Don’t Wake Me Up” both peaked at #10. (“Turn Up The Music” is a 3. “Don’t Wake Me Up” is a 4.) On the 2013 single “Loyal,” Brown teamed up with Lil Wayne and Tyga to discuss the question of whether these hoes are loyal, and the song peaked at #9. (It’s a 4.) In 2018, Brown got together with comedy-rapper Lil Dicky for the body-switching skit-song “Freaky Friday,” and the whole joke there seemed to be Lil Dicky wanting to be allowed to use the N-word. Somehow, that song made it to #8. (It’s a 1.)

You’d like me to stop now, wouldn’t you? Nope! Too many Chris Brown hits. In 2019, Brown deaded his beef with Drake, and the two of them got to #5 with the collaboration “No Guidance.” (It’s a 3.) A year later, Brown and Young Thug made a collaborative mixtape, and they got to #3 with their song “Go Crazy.” (It’s a 6.) Last year, Brown released his album Breezy, and it was a genuine flop; none of its singles made it out of the lower rungs of the Hot 100. But while that album was languishing, the 2019 album track “Under The Influence” went viral on TikTok and became an out-of-nowhere hit, peaking at #12 earlier this year.

Right now, as I’m writing this, Chris Brown has two songs on the Hot 100. One of them is “Under The Influence,” which is still lingering around the top 20. Late last year, Brown also appeared alongside Future on rap super-producer Metro Boomin’s track “Superhero (Heroes & Villains),” which is all about being seen as a villain. That one peaked at #8 when Metro’s album came out, and it’s still in the top 40. (It’s an 8. Future will eventually appear in this column, and so will Metro Boomin’s production.)

Chris Brown is enormously talented. He’s good-looking and charismatic, and he’s got the instincts to stay on top of a changing pop-music zeitgeist, whether that’s meant collaborating with T-Pain or with Metro Boomin. I like a lot of Brown’s music, but the whole Chris Brown saga is depressing as all hell. His continuing commercial relevance is more evidence for the argument that cancel culture doesn’t exist. There’s a good chance that Brown will appear in this column again before everything is said and done. I’m not rooting for him.

GRADE: 6/10