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.
There is something truly beautiful about histrionic teenage heartbreak — about a kid curling up on the floor and sobbing because a two-week relationship has come to an end. Anyone who’s been alive for long enough knows that these little soul-deaths are incidental and necessary and maybe even good. They’re learning experiences, rites of passage. But if you’re 14 years old, you’re not trying to hear that. You know that the world has completely crumbled beneath your feet, that nothing will ever be OK again. Maybe you’re just playacting the drama you’ve seen in movies or heard on pop songs, but that doesn’t mean you feel it any less viscerally.
Pop songs are great vehicles for that sort of drama. Pop songs don’t need to be nuanced or thoughtful. They don’t need to have grounded, mature perspective. In fact, maybe it’s better if they don’t have grounded, mature perspective. A pop song is three or four minutes long. In that tiny blip of time, a songwriter has to convey a feeling at its most intense. So a song about histrionic teenage heartache should itself be histrionic. It should come out sounding like a gut-level howl.
“Could’ve Been,” the second and final #1 hit from the pop singer Tiffany, isn’t really a song about histrionic teenage heartache. “Could’ve Been” songwriter Lois Blaisch was in her twenties when she came up with “Could’ve Been,” and she wrote the song for herself, not for Tiffany. “Could’ve Been” isn’t an especially great pop song, either; it’s a sturdy adult-contempo breakup ballad marred by some deeply canned ’80s production. But there’s still something wonderful about a 16-year-old kid making a #1 hit with a song about how this breakup has ruined the glorious future she had all planned out in her mind.
Lois Blaisch was not a professional songwriter. She was a session singer — one of many who existed on the periphery of LA’s music business in the ’80s. Blaisch, an LA native, started making her living as a singer when she was a teenager, but Blaisch never became a star the way Tiffany did. Instead, Blaisch worked as a singing waitress. She worked Bob Hope USO shows. She sang on Disney-distributed children’s records like the 1982 album Mousersize. She sang on demos for songwriters like Diane Warren. She sang commercial jingles. She worked.
Blaisch wrote “Could’ve Been” after the end of a short relationship with an oral surgeon. A few years ago, Blaisch told Songfacts, “The oral surgeon guy was full of bullshit and led me to believe he was going to finance my career and all this stuff. And I bought the whole thing… What I fell in love with was not necessarily him but all the things that he promised — all the big lies and the bullshit. He probably was just trying to score. I don’t know.”
One night in 1983, Blaisch sang “Could’ve Been” at the Hungry Hunter, a steakhouse in the San Fernando Valley town of Thousand Oaks. Two people who worked for George Tobin, the studio owner who would later become Tiffany’s manager and producer, heard the song, and they brought her in to sing it for Tobin. Tobin loved “Could’ve Been” and asked her to play it three times in a row. Soon afterwards, Tobin brought in a bunch of session musicians who were working with past Number Ones artist Kim Carnes, and he recorded Blaisch singing the song. (Tobin co-produced Carnes’ 1980 cover of Smokey Robinson’s “More Love,” which peaked at #10. It’s a 6.)
Tobin bought Blaisch’s publishing, and he got her an offer to sign with MCA, but she turned it down. Three years later, Tobin still owned the rights to “Could’ve Been.” In 1986, Tobin signed the 14-year-old Tiffany Darwish, and he recorded her singing “Could’ve Been.” For the Tiffany record, Tobin actually used the original instrumental track from the Lois Blaisch demo; he just took Blaisch’s voice off of the song and made a few changes, speeding the track up a bit and adding a guitar solo. When he recorded the Tiffany version, Tobin still thought of the song as a demo. He sent Tiffany’s version of the song to different singers — Dolly Parton, Crystal Gayle, Natalie Cole — but none of them wanted it. When Tiffany released her own self-titled debut album a couple of years later, “Could’ve Been” was the last song on it.
Nobody was expecting big things from that Tiffany album, but her cover of the Tommy James And The Shondells oldie “I Think We’re Alone Now” was an out-of-nowhere #1 smash. After that hit, Tobin released “Could’ve Been” as Tiffany’s next single. (Blaisch says that the contract she signed said that Tobin wouldn’t have to split the publishing if the song came out as a single, so maybe that had something to do with the decision.) Tiffany herself was happy that “Could’ve Been” became a single because she thought that the song, more than “I Think We’re Alone Now,” showed what she could do as a singer. She was not wrong.
On the original “Could’ve Been” demo, Lois Blaisch sounds smooth and breathy. She sounds like an adult, which is what she was. Blaisch’s version is probably more technically precise, but Tiffany actually sounds more viscerally connected to the track — a weird thing, considering that Tiffany didn’t write the song and didn’t experience the things she was singing about. Tiffany didn’t sound like a teenage singer. Her voice was husky and intense and professional. She sounded like she was in her thirties, and that was always part of the whole Tiffany sales pitch. But there’s still a rawness to Tiffany’s “Could’ve Been” vocal that I find weirdly appealing. She has to strain for some of those notes, but she also sounds genuinely wounded.
“Could’ve Been” is a simple, well-written song. With just a few words, Blaisch captures the stung feeling of the freshly dumped: “The flowers you gave me are just about to die/ When I think about what could’ve been, makes me want to cry.” (Blaisch says that she was looking at actual non-metaphorical dying flowers when she wrote that line.) The imagery is a bit obvious, but it also resonates. The hook — “could’ve been so beautiful, could’ve been so right” — has a sharp, clean melody. “Could’ve Been” could’ve been a country song. Probably should’ve been.
The real problem with “Could’ve Been” is the production. Tiffany, who’d tried to make it as a country singer before signing on with Tobin, puts her weight into the song, and the tinkly piano sounds nice enough. But every other element on “Could’ve Been” — the gloopy synth-strings, the booming drum-thuds, the replacement-level guitar solo — sounds cheap and chintzy and hacky. None of it serves the song. When “Could’ve Been” reached #1, the recording was already years old, and you could tell; it’s pure early-’80s cheese. But the vocal and the song itself are both pretty nice, and Tiffany already had momentum.
Kids could appreciate the idea of this girl their age singing about the life she’d never get to live with someone else. Parents could buy the tape for their kids for Christmas without worrying about there being anything objectionable on it. So “Could’ve Been” became Tiffany’s second straight #1 hit. (The song also topped Billboard‘s Adult Contemporary chart, which is pretty funny considering that the person singing it was not an adult.)
“Could’ve Been” never had a proper music video; in her Songfacts interview, Lois Blaisch theorizes that nobody thought that teenage Tiffany could be expected to act out the grown-up heartbreak depicted in the song. Instead, MCA used footage of Tiffany singing the song live, with the audience swaying all around her, as the official video. The audio on that live video isn’t great, but I guess it meant that MTV had something to play.
Blaisch never wrote another hit after “Could’ve Been.” She wrote songs for ’90s cartoons like Sailor Moon and Street Sharks. She got a Grammy nomination for co-writing a song for Quincy Jones protege Ernestine Anderson. She has nice things to say about Tiffany’s version of the song.
Tiffany had more hits after “Could’ve Been,” but those hits didn’t last for long. After “Could’ve Been,” Tiffany’s next single was a gender-flipped cover of the Beatles’ “I Saw Her Standing There.” (Her version of the song is a 3. The Beatles’ 1964 original, released as a B-side in the US, got enough airplay to peak at #14.) The self-titled Tiffany album sold four million copies, and she spent the summer of 1988 on tour, with opening act New Kids On The Block, a group that will eventually appear in this column. That same year, George Tobin and Tiffany’s mother got into a court battle over control of her career. Tiffany petitioned the court to become an emancipated minor, but her petition was shot down, and she went to live with her grandmother.
In 1989, Tiffany released her Tobin-produced sophomore LP Hold An Old Friend’s Hand. The album went platinum, and lead single “All This Time” peaked at #6. (It’s a 4.) That was Tiffany’s last top-10 hit. Her next two albums were commercial failures, and MCA dropped her in the early ’90s. In 1992, at the age of 20, Tiffany got married and became a mother, and she stepped away from public life.
Tiffany returned in the ’00s, doing the sorts of things that once-famous people did in the ’00s. She posed for Playboy. She competed on reality shows like Celebrity Fit Club and I’m A Celebrity…Get Me Out Of Here! She acted in the made-for-cable movies Mega Piranha and Mega Python Vs. Gatoroid, the latter of which also starred Tiffany’s late-’80s teen-pop peer Debbie Gibson. In that one, Tiffany and Gibson had a fight scene. Later on, they toured together as part of a big ’90s-nostalgia package, even though they both technically had their biggest hits in the ’80s. (Debbie Gibson will eventually appear in this column.)
The life of a former teenaged hitmaker does not seem especially glamorous, but Tiffany is still touring and recording today, and she seems like a nice person who’s grateful that she got to be a part of so many people’s lives. When you think about how things went for so many of the other people who made hits in the ’80s — how many of them just aren’t alive today — that doesn’t seem so bad.
BONUS BEATS: Here’s eventual winner Carrie Underwood singing an impressive version of “Could’ve Been” on a 2005 episode of American Idol:
(Carrie Underwood will eventually appear in this column. So will Idol judge Paula Abdul.)
THE NUMBER TWOS: The Bangles’ razor-edged, hard-stomping, Rick Rubin-produced cover of Simon & Garfunkel’s “Hazy Shade Of Winter” peaked at #2 behind “Could’ve Been.” It’s a 9.
THE 10S: Prince’s majestic, euphoric real-talk put-down “I Could Never Take The Place Of Your Man” peaked at #10 behind “Could’ve Been.” I said bay-baaay, it’s a 10.