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.
“Falling in love is so bittersweet,” Whitney Houston wails. “This love is strong. Why do I feel so weak?” But falling in love doesn’t sound bittersweet, and Whitney Houston doesn’t sound the slightest bit weak. Instead, she sounds like an volcano of joy, an unstoppable natural force of pure exhilaration. At least on paper, “How Will I Know,” Houston’s second chart-topper, is a song about uncertainty — about feeling your way around in the dark, trying to understand if someone else feels the same way you do. But that’s not how Houston sings it. Instead, Houston sings “How Will I Know” as if she can barely contain the excitement that comes along with that uncertainty. She sings it like she already knows.
“How Will I Know” only fell into Houston’s hands because Janet Jackson said no. The song came from George Merrill and Shannon Rubicam, a married couple from Seattle who sang backup on Deniece Williams’ 1984 chart-topper “Let’s Hear It For The Boy” and who recorded as the duo Boy Meets Girl. Boy Meets Girl had just signed to A&M, and they’d released their not-that-successful self-titled debut in 1985. (Later on, Boy Meets Girl peaked at #5 with 1988’s “Waiting For A Star To Fall.” That one is a 7.) Merill and Rubicam wrote “How Will I Know” specifically with Janet Jackson in mind, so when her managers turned it down, they were severely bummed. (Janet Jackson will make her first appearance in this column pretty soon.)
Gerry Griffith, an A&R exec at Arista, heard Merrill and Rubicam’s “How Will I Know” demo, and he was convinced that it was perfect for Whitney Houston. Clive Davis agreed. Griffith and Davis were putting a ton of resources into assembling Houston’s debut album. They had smooth R&B tracks for the album. They had gloopy adult-contempo love songs. They had show-stopping ballads. But they didn’t have a bright, anthemic pop song that could help cross Whitney Houston over to the young and largely white audiences who watched a whole lot of MTV. They knew that “How Will I Know” was the song that would make her takeover complete.
At first, Merrill and Rubicam didn’t want to give “How Will I Know” to Houston. They’d never even heard of Houston. Arista had the same problem when the label tried to recruit Narada Michael Walden to produce the song. Walden was a former mid-level R&B star who’d become a producer. (Walden’s highest-charting Hot 100 single, 1979’s exuberantly funky “I Don’t Want Nobody Else (To Dance With You)” peaked at #47.) At the time, Walden was working on Who’s Zoomin’ Who?, the slick 1985 comeback album from Whitney Houston’s old family friend Aretha Franklin. Walden knew that was an important album, and he didn’t want to take time out to work with some unproven talent. But the Arista execs managed to convince Merrill, Rubicam, and Walden that they should make Whitney Houston a priority.
Walden wanted to rewrite the song, and after some back-and-forth, Merill and Rubican agreed. Walden punched up the beat, switched the chord progression, and tinkered with some lyrics; he ended up getting co-writer credit. Walden produced “How Will I Know” and Aretha Franklin’s “Freeway Of Love” in the same session. (“Freeway Of Love” peaked at #3. It’s a 7.) On “How Will I Know,” Whitney’s mother Cissy Houston sang backup, and future American Idol judge Randy Jackson played bass.
“How Will I Know” is the only Walden production on Houston’s self-titled debut, and it jumps right out. Where most of the album seems concerned with selling the 22-year-old Houston as a mature, adult artist, “How Will I Know” is bubbly and giddy and immediate. The song is prime mid-’80s dance-pop, synthy and zippy and full of precise little machine-tooled hooks. Where most of Houston’s early songs are built around showing off Houston’s miracle of a voice, “How Will I Know” forces Houston to serve the song, to keep up with the bright but unforgiving techno-pop pace.
Ultimately, though, “How Will I Know” probably does a better job showing off Houston’s voice than anything else on that first album. Houston just goes off on this thing. It’s amazing to behold. Houston sells the emotion of the song, sounding like she’s utterly caught up in this dazzling, exciting, world-ending crush. She also nails every little melodic turn. Singers with Houston’s insane gifts sometimes get so caught up in their voices that they can lose the thread of the song. Houston even does that sometimes. On “How Will I Know,” though, she nails it.
But even in the context of a song as fast and bubbly as this one, you can still hear the power and control in her voice. There’s a lot of gospel in her delivery, in the unearthly joyous yelps and whoops and out-of-nowhere high notes. (There’s a whole lot of gospel in those backing vocals, too.) And while Houston never fully cuts loose on “How Will I Know,” she also keeps her abilities in full view. You can hear that voice bursting its way out of the song, ready to dive and curl and soar. The biggest note — the “how will I knoooooow” just as the sax solo kicks in — is enough to give a motherfucker goosebumps.
For the “How Will I Know” video, Houston worked with director Brian Grant, who’d already made videos for hits like M’s “Pop Muzik” and Olivia Newton-John’s “Physical.” Grant’s “How Will I Know” video is ludicrous, with Houston roaming around a psychedelic-pastel hall of mirrors and looking genuinely taken aback everytime the ridiculous ’80s dancers pop out at her. (Arlene Phillips, a future host on various UK dance-competition shows, did the choreography.) It’s pure, overwhelming ’80s cheese, but Houston’s movie-star smile does a whole lot to make it work.
Near the end of the video, Aretha Franklin shows up for a second on a video screen, so that’s fun. With Franklin’s cameo and with the line “I’m asking you cause you know about these things,” I think we have to consider the possibility that Whitney Houston is singing this whole song to Aretha Franklin, asking her for advice. I hope that’s what’s going on, anyway. It’s a shame we never got to see the full jukebox-musical version of that scene.
“How Will I Know” had a job to do, and it accomplished its mission. Houston had already landed her first #1 pop hit with the ballad “Saving All My Love For You,” but “How Will I Know” is her first true crossover moment — the point where it becomes obvious that she’s an unstoppable no-shit pop phenomenon. I can’t help but admire the meticulous logic of Arista’s whole project with that first Houston audience. First, they made sure R&B fans knew what Houston could do. Then, with “Saving All My Love For You,” they turned her into an adult-contempo titan. Finally, Arista made kids love Whitney Houston, too. Those kids embraced “How Will I Know,” and the track knocked “That’s What Friends Are For,” the big hit from Houston’s cousin Dionne Warwick, out of the #1 spot. (If Warwick had made “That’s What Friends Are For” six months later, Houston absolutely would’ve been on it, and the song might have been even bigger.)
As songwriters, George Merrill, Shannon Rubicam, and Narada Michael Walden will be in this column again. As a producer, Walden will also return to the column. And Whitney Houston will, of course, be back in the column many more times. We’ll see her again soon.
BONUS BEATS: In 1996, the Lemonheads released a mostly-acoustic, gender-flipped cover of “How Will I Know” as a B-side. Their version starts off deadpan and sardonic, but midway through, you can almost pinpoint the moment where Evan Dando realizes that it’s a great fucking song and gets into it. Here’s the Lemonheads’ take on the song:
(The Lemonheads’ highest-charting single, 1993’s “Into Your Arms,” peaked at #67.)
BONUS BONUS BEATS: Here’s Toro Y Moi’s video for the 2013 single “Rose Quartz,” which has a subtle “How Will I Know” sample:
BONUS BONUS BONUS BEATS: Here’s the soft, tender “How Will I Know” cover that Sam Smith released in 2014:
(Sam Smith’s highest-charting single, 2014’s “Stay With Me,” peaked at #2. It’s a 6.)
BONUS BONUS BONUS BONUS BEATS: Here’s Kelly Clarkson singing “How Will I Know” on her talk show last month:
(Kelly Clarkson will eventually appear in this column.)