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Toni Braxton’s “Un-Break My Heart”

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.

It could’ve gone wrong so many ways — not because it was risky but because it was not risky. Toni Braxton didn’t want to record “Un-Break My Heart,” easily the biggest hit of her entire career, because she thought she’d already made too many sad, melodramatic relationship songs. You can see why she wouldn’t want it. Braxton is a smooth, sophisticated R&B singer, and “Un-Break My Heart” isn’t smooth or sophisticated. It isn’t even really R&B. It’s grand and hammy adult-contempo balladry, and it came from the people most associated with grand, hammy adult-contempo balladry.

Diane Warren wrote “Un-Break My Heart.” David Foster produced the song. Earlier in 1996, the team of Warren and Foster had made Céline Dion’s “Because You Love Me,” another #1 hit. It’s easy to imagine “Un-Break My Heart” being sung by Céline Dion. It’s just as easy to someone like LeAnn Rimes or Gloria Estefan singing the song. If that had happened, “Un-Break My Heart” might’ve been a hit, but the song would’ve remained in the realm of waiting-room radios or customer-service hold music.

“Un-Break My Heart” is in the realm of waiting-room radios and customer-service hold music, but the song also transcends all of that. The next time you’re stuck on the phone for 45 minutes, waiting to talk to a human being about your health plan or about unexplained charges on your debit card, then “Un-Break My Heart” might, for a couple of minutes, make you forget the deep unpleasantness of whatever you’re doing. If anyone other than Toni Braxton had sung the song, “Un-Break My Heart” would just be one more deathly-boring minor trial. Braxton turns it into something else — maybe even into art.

There’s no big, exciting story behind “Un-Break My Heart.” One day, the title popped into Diane Warren’s head, and she wrote the song around that title. When she recorded a demo version of the song, Warren used a keyboard to mimic Spanish-guitar sounds. She played the song for Clive Davis, who didn’t like the way Warren rhymed “pain” with “rain” but who immediately thought of Toni Braxton anyway. Braxton was signed to the Arista subsidiary LaFace, and Warren’s friend David Foster took the song to LaFace boss Babyface at a video shoot. When he played the demo for Babyface, Foster said that he’d produce the song in a higher key for Braxton. Babyface disagreed, arguing that “Un-Break My Heart” would sound “really sexy” if Braxton sang it lower.

“Un-Break My Heart” discusses romantic devastation in deeply clichéd ways — not just the rhyming of “pain” with “rain” but also the total lack of specificity for this particular heartbreak. Maybe that’s why Toni Braxton didn’t want it. “Un-Break My Heart” is a Hallmark-card song, a collection of basic-ass phrases that could apply to just about any sad relationship situation: “Take back that sad word ‘goodbye’/ Bring back the joy to my life/ Don’t leave me here with these tears/ Come and kiss this pain away.” Even the Spanish guitars on the song were pretty overused at the time. David Foster had used that same kind of guitar on Madonna’s 1995 ballad “You’ll See,” and he specifically cited Bryan Adams’ “Have You Ever Really Loved A Woman?” as an inspiration for the sound of “Un-Break My Heart.” (“You’ll See” peaked at #6. It’s a 7.)

Despite all of its banalities, “Un-Break My Heart” is a solidly written song with a big hook. But David Foster’s canned-orchestra production style has buried a whole lot of solidly written songs with big hooks. He’s a historic master of arrangements that make it so that the banalities are all you can hear. By rights, “Un-Break My Heart” should be one more adult-contempo mediocrity, but Toni Braxton wasn’t willing to let that happen. Braxton might not have liked “Un-Break My Heart,” but she didn’t let that stop her from pushing the song into the stratosphere.

“Un-Break My Heart” is a textbook case of a singer elevating a song. Braxton starts “Un-Break My Heart” in deep-murmur torch-singer mode. She sounds like she’s softly coaxing someone back — less devastated, more persuasive, fully comfortable within the lower end of her vocal range. But when the chorus comes in, you can hear real hurt. Braxton doesn’t bother selling the cleverness of the imagery — a heart unbroken, tears uncried. Instead, she taps right into the raw ache of the sentiment. When she suddenly flies into a falsetto on the word “tears,” it almost sounds like her voice breaking. For the grand-finale key change, Braxton doesn’t sound like she’s forcing the melodrama. Instead, she sounds wracked and tortured — as if she’s just realizing the extent of her own pain while she’s trying to describe it.

Toni Braxton’s peers, singers like Whitney Houston and Mariah Carey, were essentially R&B singers who knew how to lock into pop-ballad mode. Braxton worked differently. When Braxton was in pop-ballad mode, she was still a full-on churchy R&B singer. That comes through in the final moments of “Un-Break My Heart,” where Braxton rasps and howls and really lets her voice loose. Braxton never sounds like she’s showing off on “Un-Break My Heart.” Instead, she sounds like the passion of the performance has seized her and told her what she needs to do. Her delivery turns choppy and feverish. At the end of the song, Braxton lets out a soft Ric Flair “wooo,” and she sounds slightly overcome with what she’s just done.

LA Reid came in to help with the “Un-Break My Heart” vocal arrangements, and maybe that’s why we get that nice little coda. While Braxton’s lead vocal goes supernova, the backing vocals keep things anchored, chanting quietly underneath her: “Say that you love me, say that you love me, tell me you love me.” The backing singers are Braxton herself and the former teenage phenom Shanice Wilson. (Shanice’s highest-charting single, 1991’s “I Love Your Smile,” peaked at #2. It’s a 6.) Those backing vocals and the Spanish guitars sound like they’re trying to console Braxton, and she doesn’t sound like she’s ready to be consoled by anything short of an unbroken heart.

For the “Un-Break My Heart” video, director Billie Woodruff, who’d also done Braxton’s “You’re Makin’ Me High” clip, had a fairly original take on the track. In the video, Braxton’s not sad because she’s been dumped. She’s sad because her main squeeze — played by supermodel Tyson Beckford as the type of guy who does handsome-man tai chi in silk pajamas on his immaculately manicured front lawn — dies in a motorcycle wreck.

Woodruff was inspired by the Barbra Streisand version of A Star Is Born, and he even had Braxton styled to look like Streisand. The video goes all-in on the operatics, with Braxton clutching Beckford’s body in the middle of the street and then wailing in front of a dramatically lit orchestra. It’s the kind of video where she does her mourning while wearing lacy lingerie, and the ultra-fake textures of the thing work for me completely. Last night, I probably watched the “Un-Break My Heart” video three times in a row while high. All that slick drama felt weirdly hypnotic.

With so many big, sad ’90s ballads, I felt like I could see the machinery at work, and it kept the songs from working on me. I was a teenager, so I felt like I was above all that manipulative pop product, and those songs’ producers and arrangers didn’t seem to care that they were smashing me with worn-out trope after worn-out trope. “Un-Break My Heart” pulled all the same sonic tricks as the others, but it felt different. The song was omnipresent. “You’re Makin’ Me High” needed record-label shenanigans to reach #1; “Un-Break My Heart” did not have that problem. Whenever I’d hear “Un-Break My Heart” in a grocery store or someone’s mom’s car, it felt both sad — really sad, not just demonstratively sad — and reassuring. It became a friendly sort of presence.

When “Un-Break My Heart” had its long run at #1, it was the early days of pop radio throwing house-music drums under every big ballad. Toni Braxton wasn’t like Mariah Carey, recording whole new vocals to radically reimagine her songs for the dancefloor. There were a lot of “Un-Break My Heart” remixes, and they all used the vocals from the original. But the house remix that I heard on the radio a lot came from house master Frankie Knuckles, and his version didn’t sound too terribly obvious. Instead, Knuckles decorated his house thump with shivery strings that paired nicely with the song’s outsized feelings. He made it sound like a disco song.

By the time “Un-Break My Heart” finally fell out of the #1 spot, Toni Braxton’s Secrets album had already gone quadruple platinum, and it would eventually move another four million copies. But Braxton wasn’t getting much in the way of royalties. She tried filing a lawsuit against Arista and LaFace, and it didn’t go forward. She declared bankruptcy, just as her LaFace labelmates TLC had done. Those Arista and LaFace contracts must’ve been terrible.

While she was trying to get paid, Braxton went to Broadway, taking the role of Belle in the Beauty And The Beast stage musical. Eventually, she signed a new deal with LaFace and followed Secrets with her 2000 album The Heat. R&B had changed a lot in the four years since Secrets, but Braxton navigated those changes just fine. For “He Wasn’t Man Enough,” the first single from The Heat, Braxton worked with then-dominant producer Rodney Jerkins, whose work will show up in this column soon enough. Braxton handled Jerkins bloopy bleeps and stop-start drum machines with aplomb, and “He Wasn’t Man Enough” peaked at #2. (It’s an 8.)

“He Wasn’t Man Enough” was Toni Braxton’s last top-10 hit. Braxton has kept working since then. She’s jumped around to a lot of labels and made a lot of music. Apparently, she and Babyface didn’t have any hard feelings; their 2014 collaborative album Love, Marriage & Divorce was a low-key gem. Braxton has acted onstage and in Lifetime movies. She had a Vegas residency for a while. She and her sisters have starred in a bunch of seasons of the reality show Braxton Family Values. Toni’s younger sister Tracy died of cancer last month at 50.

Toni herself has had some health problems over the years, including lupus and an angina. She also became a big advocate for people with autism after her son was born autistic. Braxton was briefly engaged to Cash Money Records boss Birdman — a celebrity couple that nobody saw coming. (As half of the Big Tymers, Birdman’s highest-charting single is 2002’s “Still Fly,” which peaked at #11.) Toni Braxton presumably won’t appear in this column again, but she’s always seemed cool, and she remains a great singer. “Un-Break My Heart” was a singular record for Braxton, and she deserves enormous credit for working within the sound of the moment and building something emotionally resonant out of what she was given. Nobody else could’ve done what she did with that song.

GRADE: 8/10

BONUS BEATS: Here’s the “Un-Break My Heart” cover that Weezer released in 2010, which is way better than it had to be:

(Weezer’s highest-charting single, 2005’s “Beverly Hills,” peaked at #10. It’s a 7.)

BONUS BONUS BEATS: Here’s footage of Jennifer Lopez covering “Un-Break My Heart” at a Las Vegas show in 2015, which is way worse than it had to be:

(Jennifer Lopez will eventually appear in this column.)

BONUS BONUS BONUS BEATS: Here’s Andy Samberg, Joe Lo Truglio, and Damon Wayans Jr. singing along with “Un-Break My Heart” on a 2016 episode of Brooklyn Nine-Nine:

(The highest-charting single from Andy Samberg’s group the Lonely Island, the 2010 Akon collab “I Just Had Sex,” peaked at #30.)

BONUS BONUS BONUS BONUS BEATS: Here’s the drag performer Willam’s video for the self-explanatory 2018 “Un-Break My Heart” parody “Unshart My Fart”:

BONUS BONUS BONUS BONUS BONUS BEATS: Here’s Little Dragon playing a slick, percolating “Un-Break My Heart” cover on Swedish TV in 2020:

THE NUMBER TWOS: En Vogue’s “Don’t Let Go (Love),” a wailing, snarling Organized Noize-produced show-stopper from the Set It Off soundtrack, peaked at #2 behind “Un-Break My Heart.” It’s a 9.

THE ASTERISK: When people talk about the Hot 100 being fucked up in the ’90s, the first thing that they usually mention is No Doubt’s chiming new wave dirge “Don’t Speak.” Because No Doubt never officially released “Don’t Speak” as a single, the song never charted on the Hot 100. But “Don’t Speak” did top the Billboard Radio Songs chart for an insane 16-week run, starting while “Un-Break My Heart” was at #1 on the Hot 100. If “Don’t Speak” had been able to compete, it absolutely would’ve appeared in this column. It’s a 7.

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