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.

I think I’ve been more than fair to Fergie. Stacy Ann Ferguson, the former child actor and girl-group singer, joined the Black Eyed Peas in 2003, and she helped turn that group into a pop-rap colossus. Then, a few years later, Fergie went solo, and she did better for herself than anyone could’ve anticipated. Fergie’s first two chart-toppers, “London Bridge” and “Glamorous,” are trashy, fun trifles. “Fergalicious,” the #2 hit that Fergie released in between those two singles, is trashier and more fun than either of them; it’s also a genuinely good song. (“Fergalicious” is an 8.) In previous columns, I’ve had some pretty nice things to say about Fergie. But when it comes to Fergie’s third chart-topper, I’m sorry. I can’t do it. It’s time to be a big critic now.

Fergie was able to achieve solo pop stardom in part because she was so adaptable. She could dance better than most power-belter singers, and she could belt harder than most pop stars who did a whole lot of strenuous choreography. She could rap, too — not as well as most actual rappers, but better than most pop singers. Fergie was into her thirties when she found solo stardom, but she happily embraced a bright-plastic teen-pop aesthetic. On those early singles, Fergie refused to take herself too seriously. But “Big Girls Don’t Cry” works against all of that. It’s a sincere adult-contempo ballad about growing up enough to realize that you have to break up with someone. Who wanted that from Fergie?

“Big Girls Don’t Cry” is written in deeply childish language, but it’s a song about not being a child, about recognizing the moment that you need to move on. Underneath Fergie, the music goes for acoustic singer-songwriter grace, and it doesn’t get anywhere near that. The song also requires Fergie to sing big notes in tender, sensitive ways, and she doesn’t get anywhere near that, either.

“Big Girls Don’t Cry” represents a big left turn for Fergie, and there’s nothing wrong with that. But this is one of those left turns where the car skids out and plows through a barricade. The track works against most of Fergie’s strengths, but it’s not like another singer could’ve saved it. “Big Girls Don’t Cry” is just a bad song. But someone clearly wanted this particular bad song from Fergie, since it made her the rare pop star to notch three #1 hits from one album.

Fergie has said that she wrote “Big Girls Don’t Cry” before she joined the Black Eyed Peas and that the song, like all the songs on her debut LP The Dutchess, is based on something that happened to her in real life. (I would love to hear more about why “Fergalicious” is a true story, but who am I to cast doubt on the idea of boys lining down the block just to watch what she got?) Fergie hasn’t said more about the story behind “Big Girls Don’t Cry,” but the story doesn’t really matter. Lyrically, it’s a rote and and leaden version of the standard sensitive breakup song. It’s as mawkish as any of the songs in that category, and it’s more awkward than most of them.

“Big Girls Don’t Cry” might have been slightly ahead of its time in the way that it uses self-help terminology, which wasn’t quite so prevalent in pop music at the time. Fergie sings that she has to be on her own and gives her ex a variation on the old “it’s not you, it’s me” line: “I hope you know, I hope you know/ That this has nothing to do with you/ It’s personal, myself and I/ We got some straightening out to do.” Sure. Makes sense. But then the chorus turns literally childish: “I’m gonna miss you like a child misses their blanket/ But I’ve got to get a move on with my life/ It’s time to be a big girl now, and big girls don’t cry.”

I’ve been trying to put my finger on why I find the “Big Girls Don’t Cry” chorus so aggravating. Maybe it’s the way that Fergie seems to be asking for sympathy and understanding while dumping someone. Maybe it’s the little-kid imagery, which carries the whiff of grown-ass adults complaining about the cold realities of adulting. Or maybe it’s just that Fergie sounds fucking annoying — reaching for big notes without leaving her breathy vibrato, as if she can’t let go of the idea that her empowering breakup anthem should still be somehow seductive.

Like most of Fergie’s big hits, “Big Girls Don’t Cry” follows the precedent of another big hit from the same era. Fergie released The Dutchess only a few weeks after Beyoncé came out with B’Day, so there’s no way that “Big Girls Don’t Cry” is an actual “Irreplaceable” ripoff. The two songs don’t really sound alike, and the messages are almost diametrically opposed. But I’m sure Fergie and her handlers noticed that Beyoncé had just scored an earthshaking success with a single that drew on the aesthetic and lyrical style of ’90s singer-songwriter pop. I’m sure that played into the decision to release “Big Girls Don’t Cry” as a single.

It’s probably unfair to compare “Big Girls Don’t Cry” to “Irreplaceable,” but both songs stomp around in the same sandboxes, and the results are so dramatically different. “Irreplaceable” isn’t one of my favorite Beyoncé singles, but it’s sharp and hard and finely observed. The construction is laser-precise, and the hooks land hard, but Beyoncé really sells the song’s toughness. “Big Girls Don’t Cry” goes for vulnerability instead of strength, but the vulnerability comes out sounding like a pose, and the hooks just get on my nerves.

Fergie is one of the two credited songwriters of “Big Girls Don’t Cry”; the other is Toby Gad, a German-born pop professional who started off as a protege of Milli Vanilli svengali Frank Farian. Gad had some success as a young man in the European pop world, and then he moved to New York in the early ’00s. There, he did a lot of work with also-ran pop artists like Willa Ford and Sita. “Big Girls Don’t Cry” was Gad’s first real hit, but he would help write more. His work will appear in this column again.

Black Eyed Peas leader produced “Big Girls Don’t Cry.” He hadn’t really made a big pop ballad before that. Talking to Billboard around the time that The Dutchess came out, will said that the song “really pushed” him as a producer and that he “did an Edie Brickell type of production” for the track, which is some real goofy shit. Maybe aimed too low, or maybe he just didn’t know what the fuck he was doing. Either way, there is very little of Edie Brickell’s charming loopiness on “Big Girls Don’t Cry.” Instead, the song hits all the usual generic-ballad notes, with its “More Than Words“-ass acoustic session-hack guitars and its obvious string-swells. (Ron Fair, the guy who signed and produced Christina Aguilera, arranged the strings and sang backup on “Big Girls Don’t Cry,” and those strings definitely sound like some Ron Fair shit.)

Fergie’s vocals on “Big Girls Don’t Cry” are all breathy and flirty, even when she’s singing about moving on and being by herself. There’s a distinct self-satisfaction when Fergie sings on the first verse about her need to “be with myself and center/ Clarity, peace, serenity.” When the song suddenly swells up on the chorus and Fergie goes for desperate sadness, the transition is jarring, and it’s even more jarring when she goes back to let’s-play-house stuff: “Like the little schoolmate in the schoolyard, we’ll play jacks and Uno cards/ I’ll be your best friend and you’ll be my Valentine/ Yes, you can hold my hand if you want to.” I don’t even know why that stuff is in there, unless it’s to introduce the idea that Fergie needs to go back home after playing around with the guy.

“Big Girls Don’t Cry” is just a terribly incoherent song, and I’m not sure that it even knows what it wants to be. You probably can write a playful-but-sensitive breakup song, but this ain’t it. The basic idea comes across just fine: Fergie will always have warm feelings toward this person, but she needs to fix herself before she can commit to anything. The problem is that the song can’t commit to anything, either. It wants to be charming and childlike, and it also wants to be strong and grown-up. Rather than walking a line between those extremes, the track swings wildly from one side to the other, and its hook is way too slickly self-pitying to engender any real empathy. When I hear breakup songs, I usually feel band for the person singing, or the target of the lyrics, or sometimes both. With “Big Girls Don’t Cry,” I just want all these people to go away.

The “Big Girls Don’t Cry” video at least gives a concrete reason why Fergie needs to break up with this guy. Director Anthony Mandler, who’d also done Beyoncé’s “Irreplaceable” clip, pairs Fergie up with Milo Ventimiglia. These days, Ventimiglia is best-known as the doomed dad from This Is Us. In 2007, though, Ventimiglia was just starting his run on Heroes, and he was just wrapping up his time as Jess, the absolute best of Rory’s boyfriends on Gilmore Girls. (Don’t even come at me with that Logan bullshit. I truly don’t want to hear it.) Ventimiglia had also just played the whiny and obnoxious Rocky Balboa, Jr. in Rocky Balboa, which stood as the fun-but-absurd end to the Rocky franchise before Creed came along nine years later. Busy guy!

In the “Big Girls Don’t Cry” video, Milo Ventimiglia has cholo tattoos painted on, and I can’t tell if he’s supposed to be Latino or not. (He’s definitely, absolutely a white guy.) Fergie and Milo spend blissful afternoons draped all over each other or playing acoustic guitars, but their happiness fades when Fergie sees Milo doing a drug deal with some other sketchy-looking dudes. So she packs a bag, hugs him goodbye, and then drives her muscle car off to some warehouse, where she sings the song with her session-musician buddies. When Fergie sings, she wears a big hat. I guess you have to dress like a singer-songwriter if you’re singing a singer-songwriter song.

“Big Girls Don’t Cry” sold a lot of downloads, and the single eventually went quadruple platinum. With this one, though, radio made all the difference. “Big Girls Don’t Cry” was one of the most-played songs of the year. It did especially well on adult-contempo radio. I have to imagine that programmers were happy to get a song from a rap-adjacent pop star that didn’t sound anything whatsoever like rap music.

A couple of months after “Big Girls Don’t Cry” had its one week at #1, Fergie got engaged to her boyfriend, the radically basic actor Josh Duhamel. They’d met a few years earlier, when the Black Eyed Peas made a cameo on Las Vegas, the NBC show that Duhamel starred in. In 2007, Duhamel had been in the first Michael Bay Transformers movie, which was a huge hit. For a minute there, Fergie and Josh Duhamel looked like some kind of it couple. They got married in 2009, and they had a kid and stayed together until 2017, when they got separated. The couple divorced two years later.

“Big Girls Don’t Cry” wasn’t even the last big hit from The Dutchess. Fergie followed that single with “Clumsy,” a starry-eyed love song driven by producer’s Little Richard sample. That song got as high as #5. (It’s a 6.) Eventually, The Dutchess went platinum five times over. Fergie wasn’t in any rush to make another solo album. Instead, she returned to duty as a Black Eyed Pea. The Black Eyed Peas will eventually appear in this column, so we’ll see Fergie again in that capacity. Fergie also starred in the 2009 musical Nine with Daniel Day-Lewis. I’ve never seen that movie, but I’m fairly certain that I would not like it.

Fergie didn’t get around to releasing another solo album until 2017, when she finally came out with Double Dutchess, more than a year after releasing its lead single. That album flopped badly, but I think Fergie deserves some kind of credit for refusing to make it any less trashy than its predecessor. In her forties, Fergie was still perfectly willing to release a song called “M.I.L.F. $” and to give it a video where she and Kim Kardashian take baths in milk and strike weird horny-housewife poses. (That song peaked at #34. The album’s biggest hit, the not-bad YG collab “L.A. Love (La La),” peaked at #27.)

Fergie hasn’t been on the Hot 100 since 2016, which makes sense; she hasn’t released any music since Double Dutchess. Fergie left the Black Eyed Peas around then, and she spent a couple of years hosting The Four: Battle For Stardom, a Fox singing-contest show of absolutely no consequence. Fergie has mostly been out of the public eye for the past few years, with one big, glorious exception. In 2018, Fergie sang a truly strange Jessica Rabbit-esque version of the National Anthem at the NBA All-Star Game. Every few months, I’ll be in the shower or something, and I’ll think of Fergie’s National Anthem and just bust up laughing for no reason. Someone should’ve won an Emmy for the Draymond Green reaction shot.

In the past year, Fergie has been a little bit back in the conversation, thanks to a Jack Harlow song that’ll eventually appear in this column. I’m not expecting any kind of Fergie Fergaissance anytime soon, but I wasn’t expecting her to run up three chart-toppers from a single album, either. Sometimes, people can surprise you.

GRADE: 2/10