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. Book Bonus Beat: The Number Ones: Twenty Chart-Topping Hits That Reveal the History of Pop Music.
The Coen brothers’ 2016 movie Hail, Caesar! is a supremely silly farce about the workings of ’50s Hollywood, and one of its best scenes is about a date that’s not really a date. Josh Brolin plays a behind-the-scenes fixer who keeps his studio moving, and one of his jobs is to feed the gossip press. At one point, he sets Hobie Doyle, the fresh-faced young singing-cowboy star played by Alden Ehrenreich, up on a date with Veronica Osorio’s Carlotta Valdez, a starlet who’s pretty obviously supposed to be Carmen Miranda. Hobie and Carlotta have a cute moment together at dinner; he charms her by doing rope tricks with his spaghetti. They seem to like each other just fine, but they’re not together because they like each other. They’re together so that two twin-sister gossip columnists, both played by Tilda Swinton, can see them out together. Their date is theater, and they’re both happy to play a part.
A few years after Hail, Caesar! came out, the foxy young pop stars Shawn Mendes and Camila Cabello released “Señorita,” a supposedly-steamy duet that had the same vibe as that date scene. Mendes and Cabello went public as a couple at the same time that “Señorita” came out, which led plenty of people to believe that the two of them were together entirely for publicity purposes. The way the world works now, we’re all twin-sister gossip columnists showing up to the restaurant to hear that these two adorable kids are fixin’ to be friendly. Mendes and Cabello were visibly together for a couple of years before announcing an amicable breakup on Instagram, and Mendes has said that they really were a couple. Maybe they were, to the extent that two people can be in a relationship when they’re both jetting all over the world to play arenas and film commercials or whatever. But “Señorita” never felt like two hot young people singing about being into each other. It felt like a strategic decision, a triangulated bid for maximum appeal.
And that’s fine! Couples get together out of convenience all the time, and Mendes and Cabello were both at a point where it was convenient for them to get together, whether publicly or otherwise. When a pop-star couple publicizes its relationship status, that’s the pop machine at work. It happens all the time. When it happened with “Señorita,” though, that machine was in a moment of crisis. For most of 2019, the songs that ruled the Hot 100 were made by kids in bedrooms, not by the pop industry that worked so hard to make music precision-tooled for the widest-possible swaths of the population. Lil Nas X’s “Old Town Road” and Billie Eilish’s “Bad Guy” were twin left-field triumphs that suggested pop music was moving in bold new directions. Shawn Mendes and Camila Cabello are generational peers of Lil Nas X and Billie Eilish, but “Señorita” was not a weird, inexplicable young-folks genre fusion like the two songs that preceded it at #1. Instead, “Señorita” was the machine back at work.
Eight people are credited with writing “Señorita,” and at least some of those writers have histories of making their own weird, exciting left-field pop music. That’s not what they did with “Señorita,” though. Instead, “Señorita” is the pop machine’s attempt to approximate another outsider wave — this time, the Spanish-language Latin music that started to have a serious Hot 100 impact a few years earlier. None of the people involved with making “Señorita” came from that world, and the song isn’t really Spanish beyond its title. Instead, it’s glossy pop product without much personality. Again: Nothing wrong with that. This column couldn’t exist if I didn’t like glossy pop product; a lot of that stuff is fucking awesome. “Señorita” isn’t fucking awesome, but it’s a perfectly solid example of the machine at work.
Still, after “Old Town Road” and “Bad Guy,” it felt like such a buzzkill to see a song as flavorless as “Señorita” back on top of the Hot 100. Even if the two artists were roughly the same age as Lil Nas X and Billie Eilish, it felt like the adults were back in charge — even to the point where they’d tell these two that they had to be a couple for a little while. I’m not saying that’s what happened. I’m just saying that’s how it felt.
This column has already been over the backstory of Camila Cabello, the Cuban-born girl who first got famous as a contestant on the American X Factor, was pressed into service as a member of the fun but short-lived girl group Fifth Harmony, and who reached #1 with the well-timed breakout hit “Havana” in 2018. But this is probably the only time we’ll talk about Shawn Mendes, an artist whose route to fame was different but who served a similar function once he arrived. Mendes, like Lil Nas X and Billie Eilish, was an internet kid. He found an audience by playing acoustic cover songs on Vine, the now-defunct app that preceded TikTok. Mendes might’ve come up through social media, but his star persona had none of the spiky, absurdist quality of the other pop-star kids who developed their personas online. He was just a nice young man who wanted to be liked.
Shawn Peter Raul Mendes grew up in the Toronto suburb of Pickering, and he was a cute and talented kid who wanted to be famous. (When Mendes was born, the #1 song in American was Brandy and Monica’s “The Boy Is Mine.” In Canada, it was the Goo Goo Dolls’ “Iris.”) Neither of Mendes’ parents are Canadian. His British mother sold real estate, and his Portuguese father owned a restaurant supply business. Mendes played soccer and hockey, and he auditioned for some Disney Channel show at some point. That would not be his route to fame. Instead, he taught himself to play guitar by watching YouTube tutorials, and he started posting videos of himself singing acoustic cover songs. In 2013, the 15-year-old Mendes went viral with a video where he covered fellow Ontario teen idol Justin Bieber’s “As Long As You Love Me” for a small crowd of kids on a Toronto street, and all the other kids did the Big Sean verse. (“As Long As You Love Me” peaked at #6. It’s a 3.)
It makes perfect sense that Shawn Mendes first blew up thanks to an acoustic Justin Bieber cover. Musically, he might as well be a crossbred lab clone of Bieber and John Mayer. He plays florid acoustic guitar, and he sings high-pitched melodies in his best white-R&B voice. That’s his whole thing, and he’s never developed much of a thing beyond that. Soon enough, Mendes had a huge base of followers on Vine. You can pull up a YouTube compilation and watch Mendes singing six-second covers of pretty much every non-rap song that blew up in the early ’10s. He sang all those songs in the exact same way — making sincere faces directly into the camera, strumming a couple of guitar chords, doing sincere and quavery melisma with occasional lapses into falsetto, singing the title of the song and almost nothing else because that’s all that could fit in a Vine post. I am not the target audience for this stuff, and I never have been, but plenty of people were apparently into it.
Mendes found a manager, and that manager got him signed to Island. In 2014, the 15-year-old Mendes released his debut single, the ultra-generic ProTooled power ballad “Life Of The Party,” and it peaked at #24. Soon after that, Mendes released his debut EP, cleverly titled The Shawn Mendes EP, and toured with a couple of other teen-idol types. His full-length debut Handwritten came out in 2015, and it debuted at #1 and went double platinum. Its big hit was “Stitches,” which sounds like what might happen in the alternate universe where Justin Bieber joins Imagine Dragons and which peaked at #4. (It’s a 3.) Mendes co-wrote “Stitches” with Teddy Geiger, someone who found temporary teen-idol status a decade earlier playing a young musician on the TV show Love Monkey. (Geiger’s only Hot 100 hit, 2006’s “For You I Will (Confidence),” peaked at #29.) Geiger went on to become Mendes’ main songwriting collaborator in the years ahead.
Shawn Mendes and Camila Cabello met for the first time in 2015, when Mendes was just coming off the release of Handwritten and Cabello was still in Fifth Harmony. Mendes was the opener on Taylor Swift’s 1989 tour, and Cabello and the rest of Fifth Harmony were there to make a surprise guest appearance at the Santa Clara show. (That was when Swift had guest appearances pretty much every night.) The official story is that Mendes and Cabello wrote their duet “I Know What You Did Last Summer” on a whim backstage at that particular show, even though the track officially has a few other co-writers. Mendes and Cabello released “I Know What You Did Last Summer” as a single in November 2015, and it showed up as a bonus track on the deluxe edition of Handwritten. That was the first time that Cabello recorded anything outside the larger context of Fifth Harmony, and that song and a few others helped estrange her from the rest of the group. (“I Know What You Did Last Summer” peaked at #20.)
What the fuck is “I Know What You Did Last Summer,” anyway? It’s got strummy folk guitars, like one of the Mumford-type bands that were big at the time. When its drums come in, they’re vaguely funky, like what you might find on a Bruno Mars track. Mendes sings his parts in a keening tenor with just a hint of R&B note-bending. He’s technically accomplished, but I hear no verve in his voice at all. Even when his songs are superficially catchy, as they sometimes are, they keep me at arm’s length. I can’t get a purchase on him. He’s too slippery, in a bad way. His songs glide past without ever making any real impression on me, and this is my least favorite version of pop music. At least an extravagantly bad pop song stands out in some way. Maybe that’s why Mendes tracks become more memorable with the addition of Camila Cabello. On “I Know What You Did Last Summer,” her vocal performance is like an Alanis Morissette impression from a gifted but slightly cruel tenth grader. That’s something, but it’s not enough to push the track into memorably bad territory. It’s just bad.
I’m just beating up kids here, and I don’t feel good about it. So it’s nice to be able to say that 18-year-old Shawn Mendes managed to generate at least some level of spiky frisson on Illuminate, his 2016 sophomore album. The songs on Illuminate are still fundamentally flavorless, but their pan-genre pastiche has at least a little bit of swagger working for it. Singles like “Treat You Better” and “There’s Nothing Holdin’ Me Back” — both co-written with Teddy Geiger, among others — exist at some strange intersecting point between pop and rock. If you squint your ears hard enough, they could be half-decent ’80s radio fare, and “half-decent ’80s radio fare” neatly sums up Shawn Mendes’ ceiling. Both songs were decent-sized hits, with “Treat You Better” peaking at #7 and “There’s Nothing Holdin’ Me Back” going one spot higher. (The former is a 6, and the latter is a 5.) Illuminate, like Handwritten before it, went double platinum, though it took a few years to rack up that certification. Shawn Mendes wasn’t quite in the A-list, but when you make multiple double-platinum albums during your teenage years, you’re doing something right.
If Illuminate was a slight step forward, then Mendes’ self-titled 2018 album was a much bigger step back. It feels ridiculous to pit Shawn Mendes albums against one another, since we’re really just talking about degrees of mediocrity here, but there’s no progress on Shawn Mendes — not that I can hear, anyway. Is it progress that Mendes started singing about mental health issues on songs like the lead single “In My Blood“? On paper, sure, I guess. But I don’t think it’s enough to address issues when you can’t channel them into compelling art. I don’t think “In My Blood” is compelling art. It’s just another mediocre song, and I wish co-writer and former Number Ones artist Avril Lavigne had been the one to record it. (“In My Blood” peaked at #9. It’s a 5.)
None of the other Shawn Mendes singles reached the top 10, and the album only went platinum rather than double platinum. Shawn Mendes was still hugely successful, but things were slowing down, and they needed to be charged back up somehow. In May 2019, Mendes released “If I Can’t Have You,” a faintly dance-flavored track that he wrote and recorded with regular collaborators like Teddy Geiger and Scott Harris. That song actively sucks, but it had a little more commercial juice than anything else that Mendes had done to that point. “If I Can’t Have You” was one of many that debuted at #2 behind the unkillable “Old Town Road” beast. (It’s a 3.) The world evidently wanted frothy, uptempo pop music from Shawn Mendes. Later in 2019, Mendes gave the people what they wanted.
“Señorita,” the biggest song of Shawn Mendes’ career, did not start with Shawn Mendes. Instead, the song came out of a songwriting session that involved four people. One of them was Andrew Watt, the Post Malone producer who seemed to have an iron grip on the Hot 100 in the days before “Old Town Road.” Watt, whose credits include Camila Cabello’s “Havana,” must’ve been stressed when he went a whole five months without a #1 hit, between the Jonas Brothers’ “Sucker” and “Señorita.” Another writer at the session was Ali Tamposi, the Florida-born songwriter who’s already been in this column for her work on Kelly Clarkson’s “Stronger (What Doesn’t Kill You).” At the time, Watt and Tamposi were regularly working with former Number Ones artist Charli XCX. Charli, Watt, and Tamposi were writing together a few days a week. A little bit earlier, they wrote Charli’s 2019 track “White Mercedes” together. “White Mercedes” didn’t chart, and it’s pretty peripheral to this particular column. But I’m including it here anyway, since I’ve decided that we have to have at least one genuinely good song and video embedded in this column.
At the session where they came up with “Señorita” together, those three writers were joined by a fourth: Jack Patterson, a member of Clean Bandit, the British dance-pop group who made a few breezy, summery hits in the mid-’10s. (Clean Bandit’s highest-charting Hot 100 hit, the 2016 Sean Paul collab “Rockabye,” peaked at #9. It’s an 8.) The day of the “Señorita” session was Patterson’s first time working with Watt and his collaborators, and he was jet-lagged when he got in. The four of them spent the day working together, taking breaks for the arrival of a nail tech (they all got pedicures) and a vintage T-shirt dealer (Tamposi says she bought “a Minor Threat sweater”). All this was happening at Andrew Watt’s house. Here’s how he describes the genesis of “Señorita” in a Billboard oral history:
I was sitting in my backyard before the session, and four aliens landed in my backyard and sat with me. I had this guitar and I said, “I don’t know what to do about the session,” and they touched me and put this riff up my ass — this fingerpicking somewhere between Fleetwood Mac and José Feliciano. Then I went into the session and played the riff for Ali and Jack and Charli.
Perhaps I was simply naïve here, but I didn’t expect Andrew Watt to talk like such a fucking weirdo. If someone has zero public profile but credits on dozens of massive hits, I expect that person to talk like an accountant. Shows what I know. If Andrew Watt is a little more bugged-out and self-impressed than that, I simply must respect it. I don’t think the “Señorita” riff really sounds anything like Fleetwood Mac or José Feliciano, but it’s not a bad little riff. Watt brought the riff to his collaborators, and Tamposi says that they all sang melodies over it until they landed on the one that became “Señorita”: “We latched on to the emotion of the phrase, ‘I love it when you call me señorita.’” How could they not? It’s such an emotional phrase.
Once that original crew had a basic version of “Señorita” together, Andrew Watt sent the track to Shawn Mendes. Charli XCX apparently didn’t even consider keeping the track for herself, and I don’t think this is one of the situations where she might regret giving away a hit song to someone else. I hear absolutely zero Charli on the song, which I guess means that she’s a songwriting professional, though the song might be better if her touch was a little more evident. Watt told Mendes that he thought the song could be a duet, and Mendes agreed, but only if he could make it with Camila Cabello. Charli and Cabello were opening acts on Taylor Swift’s Reputation tour together, and then they became roundabout collaborators with this song. Mendes and Ali Tamposi recorded a “Señorita” demo, and then the song sat on the shelf for a while. First, Cabello wasn’t sure that she wanted to record it. Then she was ready, but Mendes wasn’t sure. While all this was going on, Andrew Watt brought the song to two other hitmaking producers, Benny Blanco and Cashmere Cat.
Benny Blanco has been in this column a bunch of times. Cashmere Cat has not. Magnus Høiberg is a former battle DJ from Norway who started making giddy, experimental electronic records in the early ’10s. When he started to bubble, Blanco invited him out to the US to work on tracks, and the two of them quickly became friends and collaborators. Blanco co-produced Cashmere Cat’s only Hot 100 hit as lead artist, the 2015 Ariana Grande collab “Adore,” which peaked at #93. Cashmere Cat co-produced Benny Blanco’s biggest hit as a credited artist, the 2018 Khalid/Halsey collab “Eastside,” which peaked at #9. (It’s a 7.) Cashmere Cat entered the song-machine orbit, and he worked on a lot of hits, some with Blanco and some without. We’ll see his work in this column again.
Andrew Watt always had a hard time impressing Cashmere Cat. In that Billboard article, Watt says, “I have played him song after song, and he’s been like, ‘It’s cool, but I hate it,’ every time.” So when Cashmere Cat liked “Señorita,” Watt said that he was “honored” and that he wanted Cashmere Cat to do something, anything, with the track. Benny Blanco and Cashmere Cat did some production work on the song, though it seems like they didn’t do too much to alter the demo. Cashmere Cat insists that his input was minimal: “They let me sprinkle a tiny bit of truffle salt on it. They did all of the heavy lifting. I Postmated us coffee. That’s really all I did.” Watt begs to differ: “Cashmere took it from just being really kind of simple and put some nuances in there — the ambient stuff that you hear is all Cashmere.” I don’t actually hear much ambient stuff, but if I did, maybe it wouldn’t be ambient.
For a while, Shawn Mendes, Camila Cabello, and all their collaborators didn’t make the time to finish “Señorita.” Eventually, both artists got to working on the song, both making enough changes that they got songwriting credits. They FaceTimed each other with lyrical ideas, and Cabello changed the song’s key. While Mendes was on tour, Watt flew to the UK to get him to re-record his vocals. Mendes was annoyed about it, since he didn’t want to wear out his voice before a run of London shows, but he went along with it anyway. Eventually, Mendes and Cabello got into the studio together to finish the track. When the song was being mixed, Cabello came up with a line that she really wanted to add: “You say we’re just friends, but friends don’t know the way they taste” — genuinely the sexiest lyric on the entire song. Mendes had to come back in and record extra harmonies just for that line. Eventually, the people involved all finished up the track when both Mendes and Cabello were inconveniently between album cycles.
When you hear “Señorita,” you can kind of tell that it’s a song made by committee. Lots of interesting artists had a hand in “Señorita,” but none of them brought anything interesting to the track, which feels like an intentional choice. “Señorita” isn’t built to be interesting. It’s built to float pleasantly by on the radio and maybe to evoke memories of “Despacito,” and it mostly does its job. The production is sleek. The melodies are solid. The lyrics are dumber than fuck. Camila Cabello’s character loves it when Shawn Mendes’ character calls her señorita, and she wishes she could pretend she didn’t need him. They’re in Miami, and they’re hot for each other, and that’s it. That’s the whole story. Mendes rhymes “sapphire moonlight” with “tequila sunrise.” Both of them rhyme “ooh la la la” with “it’s true la la la.” If the hooks didn’t sparkle quite like they do, then “Señorita” would be the sort of pop song that somebody might write to make fun of pop songs.
I don’t have a problem with cheese. Cheese has always had a place in pop music, and it should always have a place in pop music. For the most part, “Señorita” is perfectly passable cheese, but it never ascends to the level of good cheese. The song seems expressly written to draft on the momentum of the actual Spanish-language pop that’s become an increasingly huge Hot 100 presence in the past decade or so, but what it really recalls is the Y2K moment when a bunch of vaguely Latin-adjacent song-machine hits were getting major TRL burn. A true cheesemeister like Enrique Iglesias would’ve sold the absolute hell out of “Señorita,” but a nice Canadian boy like Shawn Mendes doesn’t have that level of commitment in him. He doesn’t smolder. Neither does Cabello, really, though she tries a little harder.
Maybe the video was supposed to take care of that aspect. Video veteran Dave Meyers directed the “Señorita” clip, and he’s the same guy who did Billie Eilish’s “Bad Guy” video, though you absolutely can’t tell. The “Bad Guy” clip is a visual feast, while the “Señorita” video is a handsomely photographed retreat into cliché. Cabello is a diner waitress, Mendes is a boy on a motorcycle, and the two of them make out sweatily in dumpy hotel rooms. They are both extremely attractive people, but they don’t generate a ton of heat together. Maybe that’s why so many were convinced that they were a fake publicity-stunt couple. Maybe they were one of those real couples who can’t convincingly portray a real couple on camera. It happens.
“Señorita” came out in June 2019. Like “If I Can’t Have You” before it, the song debuted at #2 behind “Old Town Road.” But “Señorita” had the good fortune to come out closer to the end of the “Old Town Road” run, and it hung around in the top five, keeping the right combination of streams, digital sales, and radio airplay. As the “Old Town Road” summer drew to a close, “Señorita” had its brief run at #1 in the week that Mendes and Cabello sang it together at the VMAs. Eventually, the single went quintuple platinum.
Neither Shawn Mendes nor Camila Cabello has threatened to return to the #1 spot in the time since “Señorita.” Between the two of them, they’ve only managed one more top-10 hit. In 2020, Mendes teamed up with Justin Bieber, the guy who provided so much of his blueprint, on the #8 duet “Monster.” Bieber sings rings around him on that one. (It’s a 5.) Once pandemic restrictions lifted in 2021, Mendes booked a tour to support Wonder, the album that he released the previous year. After a few shows, Mendes canceled the rest of the tour to focus on his mental health. He took some time away from the spotlight, and he played the singing voice of the titular reptile in the 2022 kids’ film Lyle Lyle Crocodile. Why did the titular reptile need to have a singing voice, you ask? Good question! I don’t know! Lyle doesn’t sing in the damn books! Crocodiles, even anthropomorphic friend-to-children ones, don’t typically sing! Last year, Mendes returned with Shawn, an acoustic singer-songwriter album that mostly leaves pop-star trappings behind. Lead single “Why Why Why” peaked at #30, and the LP flopped.
Camila Cabello released her second solo album Romance at the end of 2019, and it eventually went platinum without setting the world on fire. For a long time, that LP’s biggest hit was “Liar,” which stalled out at #52. Eventually, Cabello released a remixed version of the LP track “My Oh My” with an appearance from DaBaby, a rapper who will eventually appear in this column. That came out during the brief stretch when DaBaby could turn anything into a hit, and the remix reached #12. Cabello starred in an absolutely abysmal 2022 straight-to-streaming jukebox-musical Cinderella movie, which has entered internet infamy as the kind of thing that can make you cringe so hard you might break your face. It’s got James Corden voicing a CGI mouse, if you’re into that sort of thing.
Cabello’s next album, 2022’s Familia bricked pretty hard. Its biggest single was the Ed Sheeran duet “Bam Bam,” which may have been about Shawn Mendes and which peaked at #21. Last year, she attempted to lurch out of the B-list by riding the hyperpop wave on her LP C,XOXO. It didn’t work, but it was fun to watch her try. Lead single “I Luv It” tried a ton of different shit at once — a busy beat from Rosalía producer El Guincho, a Gucci Mane sample, a verse from future Number Ones artist Playboi Carti — and made for a fun little mess. It stalled out at #81. It wasn’t really a good song, but I appreciated its moxie. I’d rather hear a flaming trainwreck than a sensitive folk record. Follow-up single “He Knows” paired Cabello up with her 2019 chart rival Lil Nas X and didn’t even make the Hot 100. The biggest hit from C,XOXO turned out to be the Drake collab “Hot Uptown,” which had the cursed luck to come out amidst Drake’s feud with Kendrick Lamar; this column will get to that whole kerfuffle. It peaked at #62.
During the pandemic, Shawn Mendes and Camila Cabello quarantined together, doing some remote performances and marching in some protests. They adopted a dog together. They released a duet version of “The Christmas Song.” They announced their breakup in 2021, and then they were spotted together a few times in 2023 before breaking up again. They continue to say nice things about each other. About six months ago, after years of people speculating about his sexuality, Mendes said that he’s “just figuring it out like everyone.” Mendes and Cabello are both still young and hot, and I wouldn’t be shocked if one or both of them eventually return to this column, together or separately. If that never happens, they’ll always have “Señorita.”
GRADE: 5/10
