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.
Imogen Heap: What a name, right? If you’re born with a name like Imogen Heap — and it is, in fact, her real name — then you almost have to become a culty art-pop star. It’s the only thing that makes sense. Imogen Heap was kicking around the fringes of the music business for a long time before she made any real tangible pop-culture impact. I saw her open for Rufus Wainwright at a little upstairs club in Baltimore in 1999, and I don’t remember much about it. British lady, big pile of curly hair, keyboard. She seemed cool? That’s all I got.
At the time, Imogen Heap was touring on her 1998 debut album I Megaphone. The title track was on the I Still Know What You Did Last Summer soundtrack. In the years ahead, Heap would form the short-lived arty synthpop duo Frou Frou. They’d land a song on the Garden State soundtrack and cover Bonnie Tyler’s “Holding Out For A Hero” for Shrek 2. When Frou Frou broke up, Imogen Heap would mortgage her apartment to write, record, engineer and self-release 2005’s Speak For Yourself, her second solo album. That LP would feature a strange, beautiful, disorienting song called “Hide And Seek” — a song that featured nothing other than Heap’s robotically distorted singing voice.
Imogen Heap has never said what “Hide And Seek” is about, but she has given the song’s technical backstory. When she was working in the studio one day, her computer crashed. She saw a synthetic harmonizer known as the DigiTech Vocalist Workstation on a shelf, so she took it down and plugged her minidisc recorder into it, and then she sang this song that she’d written. It’s a magnetic, beautifully strange piece of music — a mood created through nothing but this blurry and pixelated voice. Heap didn’t use Auto-Tune, but “Hide And Seek” must’ve been a huge influence on the Auto-Tune experiments that people like Bon Iver would make a few years later.
A song like “Hide And Seek” never had any shot at becoming a pop hit. Instead, “Hide And Seek” found more indirect ways into mass consciousness. Shortly after the song’s release, The O.C., a beautifully ridiculous show that habitually crammed its soundtrack full of almost-famous songs, used “Hide And Seek” to score what might be its most beautifully ridiculous moment. Ben McKenzie’s Ryan Atwood, the troubled teen who’s gone to live with a rich family, is fighting with his no-good brother Trey, and Trey is strangling Ryan, maybe about to kill him. Then Mischa Barton’s Marissa Cooper, Ryan’s love interest, bursts in, grabs a gun that’s sitting nearby, and tearfully shoots Trey. “Hide And Seek” suddenly blares on the soundtrack while Trey falls in histrionic slow motion. It’s fucking insane. I love it.
In that episode of the The O.C., we hear the bridge of “Hide And Seek,” the bit where Imogen Heap sings to the person who’s presumably tearing her narrator’s life apart: “Mmm, whatcha say, mmm, that you only mean well? Well, of course you did. Mmm, whatcha say that it’s all for the best? Of course it is.” That’s the “Hide And Seek” bit that immediately lodged in a whole lot of people’s heads. Two years later, an SNL Digital Short parodied that scene from The O.C., and that bit from “Hide And Seek” once again soundtracked some histrionic murder business. (The highest-charting single from Andy Samberg’s group the Lonely Island is the 2010 Akon collab “I Just Had Sex,” which peaked at #30.)
“Hide And Seek” never made any headway on the UK singles charts, and it never landed on the Hot 100, either. But the song was in the air. The context surrounding “Hide And Seek” was funny, but the song itself was full of strange, hypnotic pathos. As aggressive Auto-Tune became part of the pop landscape, lots of other people tried to capture their own strange, hypnotic pathos; it’s more or less what Kanye West did with 808s & Heartbreak. Maybe it was inevitable that someone would sample “Hide And Seek,” that they’d turn it into a pop song. Someone did. That someone was the 20-year-old Florida singer Jason Derulo, and that sample helped power his debut single “Whatcha Say” all the way to #1.
Jason Desrouleaux — I can’t believe that’s his real name — grew up in Mirimar, a small Florida city near Miami. (When Desrouleaux was born, fellow Floridian Gloria Estefan’s “Don’t Wanna Lose You” was the #1 song in America.) Desrouleaux’s parents were Haitian immigrants who spoke Creole at home. As a kid, Desrouleaux went to performing-arts high schools, acted in musicals, and tried his hand at writing songs. In 2006, the cornrowed 16-year-old Desrouleaux won an amateur-night contest on Showtime At The Apollo. A year later — and I can’t quite figure out how this happened — Desrouleaux co-wrote and sang the hook on “Bossy,” an album track from the Cash Money Records co-founder Birdman. (Birdman’s highest-charting single, the 2006 Lil Wayne collab “Stuntin’ Like My Daddy,” peaked at #21.)
For a while, Jason Desrouleaux worked as a songwriter. He’s got a credit on “Playing With Fire,” an album track from former Number Ones artist Lil Wayne’s 2008 blockbuster Tha Carter III. Desrouleaux supposedly also wrote a bunch of other tracks for a bunch of other pop stars, though those might’ve been uncredited or unreleased, since none of them are listed on his Discogs. Eventually, JR Rotem, the big-deal pop producer who’s already been in this column for his work on Rihanna’s “SOS” and Sean Kingston’s “Beautiful Girls,” signed Desrouleaux to his Warner Bros. imprint Beluga Heights. Somewhere in there, Jason Desrouleaux became Jason Derulo — or, depending on which record cover you’re looking at, Jason Derülo.
The people involved in Beluga Heights all worked together closely. Jason Derulo and Sean Kingston both have writing credits on “Replay,” a massive reggae-adjacent hit for Iyaz, a singer from the British Virgin Islands who was also signed to Beluga Heights. (“Replay” peaked at #2. It’s a 6.) Sean Kingston also has a writing credit on “Whatcha Say,” the song that Jason Derulo eventually took to #1. In fact, there’s evidence that “Whatcha Say” was going to be a Sean Kingston song at some point. A version with Kingston’s vocals has been on YouTube since 2010. It’s not very good.
In both its Jason Derulo and its Sean Kingston forms, the first voice that we hear on “Whatcha Say” belongs to Imogen Heap. JR Rotem, co-producing with a German guy named Alexander “Fuego” Palmer, chops up Heap’s voice. On the intro, he turns her into a stutter that bounces back and forth between speaker channels. The producers speed up Heap’s voice a bit and surround it with all the accoutrements of late-’00s pop: busy drum programming, triumphal synth-horns, smeary rave keyboards, echoing heyyy chants — all that “Live Your Life” stuff. Even with those sounds slathered on top of it, the bittersweet regret of Imogen Heap’s voice still shines through, and it helps prevent the song from becoming fully generic.
On some level, “Whatcha Say” wants to be a fully generic song. Most of the production choices are chained to that discrete moment in chart-pop history. Jason Derulo, a perfectly flexible singer with a nice falsetto, doesn’t need Auto-Tune to stand out, but he uses a ton of it anyway. The lyrics all come from the viewpoint of a guy who’s cheated on his girlfriend and who wants to be forgiven — one of the most clichéd pop-song concepts in existence.
When “Whatcha Say” was still bubbling, Jason Derulo told Digital Spy that he brought JR Rotem the Imogen Heap CD after randomly buying it in a record store and that he wrote the song after his brother told him that he’d cheated on his girlfriend and that he wanted her back. Derulo said that he found his brother’s story “really compelling” and that it had a happy ending: “She did take my brother back, though, and they’re actually engaged now, so it all worked out good in the end.”
The reality was probably both messier and more boring than that, as “Whatcha Say” has seven credited songwriters: Derulo, Rotem, Sean Kingston, Imogen Heap, and three guys I’ve never heard of: Achraf Baachaoui, Leff Row, J-Lex. Those other guys don’t even have any other credits, or any existence that I can find online. It’s weird. I don’t know what’s going on there. (If I had to guess, I’d say Sean Kingston wrote the line “I know what I did wasn’t clever.” I like the idea that Kingston is secretly behind all the weird uses of the word “clever” on #1 hits.)
So “Whatcha Say” is one of those weird, mysterious song-machine products that exists entirely to fill some hole in radio programmers’ playlists. I’ll tell you what, though: “Whatcha Say” goes. As an artist, Jason Derulo has managed to avoid anonymous-professional status mostly because he’s desperately, audibly eager to please at all times. He takes this goofy nothing of a song, a song that otherwise only has that Imogen Heap sample going for it, and he launches himself into the breach. You can practically picture this guy falling to his knees and pulling Usher moves in the studio while recording. He sounds energetic and vulnerable at the same time, a rare combination, and he hits the sturdy melodic turns with real panache. I like his delivery on the bit about when the roof caved in and the truth came out and he just didn’t know what to do. He sells it.
The narrator of “Whatcha Say” is a total dog. He admits it. He wasn’t thinking about his relationship at all when he cheated, and he doesn’t offer any good reasons for her to take him back. His best sales pitch is that he’s about to become famous and that he’ll treat her better then: “When I become a star, we’ll be living so large, I’ll do anything for you.” He asks her to tell him what to say, which is some lazy shit. But he sounds so boisterous that he’s hard to resist.
The way that “Whatcha Say” is constructed, it sounds like Jason Derulo going back and forth with the Imogen Heap sample. The chorus is nothing but that moment from Heap’s “Hide And Seek,” and Heap does not sound especially amused by Derulo’s protestations. Maybe Derulo’s side of the conversation is bound to fail. Maybe he knows that but feels like he needs to make his case anyway. Somehow, this whole romantic-betrayal situation makes for an above-average club-pop song. Nobody seems that torn up about what’s going on. All the people involved, including the sampled voice of Imogen Heap, sound like they just want to dance.
There’s an intriguing push-and-pull dynamic at work on “Whatcha Say.” As a songwriter and a performer, Jason Derulo has always been driven to please as many people as possible. That’s his internal engine. He’s a pop-music golden retriever, and his neediness has helped him stay intermittently relevant for longer than anyone could’ve guessed. But “Whatcha Say,” the first Jason Derulo song that anyone ever really got to hear, has that Imogen Heap sample giving it a sense of faraway, bittersweet headiness. “Hide And Seek” is plainly not a song made for the biggest-possible audience, and even in this warped and chopped-up form, the sample lends an interesting tension to “Whatcha Say.”
As fate would have it, Jason Derulo was early on the Imogen Heap sample train. A couple of years later, Imogen Heap samples would become one of the sonic building blocks of the hazy, psychedelic subgenre known as cloud-rap. A$AP Rocky, Lil B, and Main Attrakionz have all rapped over Imogen Heap samples. Clams Casino, the producer who defined the style, essentially built his whole sound off of Imogen Heap samples. At this point, Imogen Heap’s voice only really sounds right to me when it’s a bed for some mind-blown rap expansiveness.
Imogen Heap seems perfectly happy to hear her voice sampled and refracted in all kinds of unexpected ways. She’s never become a pop star, and she’s never had a song on the Hot 100, but “Hide And Seek” and the Speak For Yourself album both went gold years after release. Heap co-wrote and co-produced the Taylor Swift song “Clean,” and she composed the music for the Broadway show Harry Potter And The Cursed Child. She’s got a great career.
Jason Derulo’s got a pretty impressive career, too. He’s also a Taylor Swift collaborator, by way of the movie Cats. But the careers of Jason Derulo and Imogen Heap have moved in opposite directions. Derulo released his self-titled debut early in 2010, after “Whatcha Say” had already gone #1. JR Rotem produced the entire LP, and it’s way more jammed with hooks than I would’ve guessed from “Whatcha Say” alone. After “Whatcha Say,” Derulo made it to #5 with the brisk, efficient “In My Head.” (It’s a 7.)
Derulo spent part of 2010 on tour as Lady Gaga’s opener, and you couldn’t ask for a more instructive contrast between artists. Gaga and Derulo were both making dance-pop hits, but Gaga was using those hits as a way to play around with pop iconography. Derulo, on the other hand, just wanted to keep making unchallenging jams that sounded great on the radio. Both of them achieved their objectives. After “In My Head,” Derulo made it to #9 with the dancehall-adjacent banger “Ridin’ Solo,” which sounds fucking awesome in the car on a sunny day. (It’s a 9.) Derulo’s self-titled album went platinum, and all three of its singles are now multi-platinum.
Jason Derulo’s boldly titled 2011 sophomore album Future History stalled out at gold, and none of its singles made the top 10. But Derulo stuck around radio playlists, and he continued to show just how shameless he could be. “Don’t Wanna Go Home,” the biggest Future History hit, is a giddy EDM track that manages to sample the Robin S classic “Show Me Love” and interpolate the Harry Belafonte touchstone “Day-O (The Banana Boat Song).” (It peaked at #14.)
Derulo’s career had some rough moments in the early ’10s. He suffered a couple of dance-induced back injuries, and he served as a judge on an Australian dance-competition show that was cancelled almost immediately. While attending the Cannes Film Festival in 2011, Derulo fell down some stairs, and the photo goes viral again and again, usually because someone falsely claims that it happened at that year’s Met Gala. But Derulo was not willing to let his moment end. Derulo forged a partnership with rising producer Ricky Reed, and he came back strong with the infernally catchy 2 Chainz collab “Talk Dirty,” which made it to #3 in 2013. (It’s an 8, and not just because 2 Chainz rhymes “sold-out arenas” with “Gilbert Arenas” and “suck my penis.”)
A year later, the “Talk Dirty” format — horny lyrics, energetically catchy Ricky Reed production, grizzled but funny guest-rapper — scored Derulo another major hit. On 2014’s “Wiggle,” Derulo teamed up with former Number Ones artist Snoop Dogg and sang that your booty is like two planets. (“Wiggle” peaked at #5. It’s another 8.) Despite the goony poetry in some of Derulo’s horniest lines, nobody was going to confuse him for a serious artist. But Derulo was a craftsman, and he just kept serving the dancefloor. Through sheer consistency, he became an oddly intriguing figure.
Jason Derulo’s 2014 album Everything Is 4 was full of big, weird swings. With that record, Derulo probably became the first person to put Stevie Wonder and Keith Urban on a song together. Those thirsty combinations didn’t always work, but Everything Is 4 also had “Want To Want Me,” an absolute monster of a pop song that went all the way to #5. (It’s a 9.) Over five years of hits, Derulo never really nailed down a persona or a sonic template, but he came up with banger after banger. Until I really sat down and looked at Derulo’s discography, I don’t think I really knew that most of his jams were his. The man just made anonymous sonic sunbeam after anonymous sonic sunbeam. I respect it.
If greatest-hits albums were still a viable commodity, Jason Derulo would have a very good one on his hands. As it is, nobody has ever regarded a Jason Derulo album as an artistic masterpiece, but the man quietly became one of his era’s most consistent singles artists. His string of hits didn’t really last, especially as the pop charts made the transition into the vibes-based playlist bait that tends to dominate today. But Derulo found a second act when he figured out that he really, really loves TikTok. Implausibly enough, we’ll see Jason Derulo in this column again.