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.
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.
“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.
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.
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:
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:
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.)