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.
Pop-chart history makes no sense. I have now written more than 700 of these columns, and that’s my main takeaway. In tracing the history of #1 hits on the Billboard Hot 100, I’ve watched new sounds and movements grow and then shrink back, and I’ve seen massive superstars rise and then fall. But there’s no real narrative to this whole thing. There is only chaos. Plenty of #1 hits are beloved classics. Plenty are fun little reminders of bygone pop-culture moments. And a whole lot of them are just absolute non-entities — songs that might as well not exist.
“She Ain’t Worth It,” the sole chart-topper from the Hawaiian teen idol Glenn Medeiros, belongs in that last category. This song came out when I was 10 years old, a brand-new and enthusiastic fan of pop music, and I have no memory of it ever existing. If there wasn’t hard-copy evidence of the song’s status, I would’ve never believed it was a #1 hit.
Really, though, “She Ain’t Worth It” has minor-landmark status in the history of #1 hits. It’s the first #1 hit that made use of a featured guest rapper — someone who could come in, knock out a few bars on the song’s bridge, and give it some extra pop juice. That wasn’t really a thing before “She Ain’t Worth It.” You could argue that Paula Abdul’s “Opposites Attract,” which reached #1 five months before “She Ain’t Worth It,” really deserves that distinction. But MC Skat Kat, the rapping guest on “Opposites Attract,” doesn’t have a featured-guest credit on the song. On top of that, MC Skat Kat wasn’t a real person — or, for that matter, a person at all. He was a fictional character, invented entirely so that Paula Abdul could dance with a cartoon character in the “Opposites Attract” video. Bobby Brown on “She Ain’t Worth It” is another story.
Bobby Brown’s guest credit on “She Ain’t Worth It” is a weird one. Brown was never a rapper; he was a singer who occasionally added little rap verses to his own songs. But Brown carried himself as a rapper, and that’s the role that he plays on “She Ain’t Worth It.” He doesn’t sing on the song. He just raps.
Brown was at the height of his fame when “She Ain’t Worth It” came out, and he was definitely way more famous than Glenn Medeiros. Brown was coming off of Don’t Be Cruel and “My Prerogative“; he couldn’t have been hotter. Even though Brown’s verse on “She Ain’t Worth It” is just eight bars — barely a cameo — he’s almost certainly the main reason why the song blew up the way it did. In the years after “She Ain’t Worth It,” plenty more hits would follow that same formula — giving pop songs an extra edge by bringing in a zeitgeisty rapper for a quick appearance.
Glenn Medeiros was lucky to get Bobby Brown on a song. Medeiros had gotten his start on Amherst Records, a small indie label based in Buffalo. By 1990, Medeiros had a joint deal with Amherst and MCA, which made him sort-of labelmates with Bobby Brown, but that’s not why Brown is on “She Ain’t Worth It.” Leonard Silver, the head of Amherst, was friends with Rick James, the troubled funk superstar. (James’ highest-charting single as lead artist, 1978’s “You And I,” peaked at #13.) Rick James, meanwhile, was friends with Bobby Brown, and I can really only imagine how skeezy those hangout sessions must’ve been. At some point, James convinced Brown to get on a song with this Glenn Medeiros kid. “She Ain’t Worth It” was already done before Brown jumped on it, but that Bobby Brown verse is presumably the only reason why the song went anywhere.
Really, though, Glenn Medeiros was lucky to have a pop career at all. Medeiros has one of those great random-connections career stories. Medeiros had grown up on the Hawaiian island of Kauai, and he was a kid when he entered a local radio station’s talent contest. (When Medeiros was born, the #1 song in America was the Beatles’ “The Long And Winding Road.”) In that 1986 talent contest, the 16-year-old Medeiros sang a version of “Nothing’s Gonna Change My Love For You,” a drippy Michael Masser/Gerry Goffin ballad that George Benson had recorded a year earlier. Benson’s original recording was not a hit, but Medeiros liked the song, and he used it to win the contest. Medeiros got to fly to Honolulu, and he was awarded $500 and a chance to record his version of the song.
A Honolulu radio station added Medeiros’ version of “Nothing’s Gonna Change My Love For You” to its playlist, and Guy Zapoleon, a Phoenix radio station’s program director, heard the song while he was on vacation in Hawaii. As a programmer, Zapoleon had an independent streak; he’s the guy who rescued UB40’s “Red Red Wine” from obscurity and set it on a path to reaching #1. Back in Phoenix, Zapoleon added “Nothing’s Gonna Change My Love To You” to his rotation, and the people of Phoenix were into it, even though they couldn’t buy the single anywhere. Amherst Records head Leonard Silver heard the song while he was at a record convention in Phoenix, and when he found out that Glenn Medeiros didn’t have a record out, he flew to Hawaii and signed the kid.
“Nothing’s Gonna Change My Love For You” fucking sucks; it’s a prime example of flavorless ’80s balladry. Maybe Medeiros’ fun backstory helped. The song became a pretty big adult contemporary hit, and it peaked at #12 on the Hot 100. In the UK, for whatever reason, “Nothing’s Gonna Change My Love For You” was huge; it sat at #1 for four weeks in 1987. Bobby Brown liked the song, too, and he sang it in some of his live shows. That’s partially why Brown decided to work with Medeiros.
After “Nothing’s Gonna Change My Love For You,” a couple of other songs from Medeiros’ self-titled 1987 debut stalled out in the lower rungs of the Hot 100. Medeiros’ 1988 sophomore album Not Me pretty much disappeared without a trace; lead single “Long And Lasting Love,” another Masser/Goffin ballad, peaked at #68. The teenage-balladeer thing wasn’t working for Medeiros anymore. In between “Nothing’s Gonna Change My Love For You” and “She Ain’t Worth It,” Medeiros’ biggest moment was probably a quick cameo in The Karate Kid Part III.
Medeiros’ 1990 album was also self-titled — the guy had three albums, and two of them were self-titled — and it was mostly written by the team of Antonina Armato and producer Ian Prince. Armato had co-written Brenda K. Starr’s 1988 hit “I Still Believe,” which peaked at #13. (In 1999, Starr’s former backup singer Mariah Carey covered “I Still Believe,” and she took the song to #4. Carey’s version is a 4.) Prince was a keyboard player and drum programmer who’d produced one song on Karyn White’s debut album.
Armato and Prince did their best to give Medeiros’ sound a bit more of a uptempo edge, bringing some of the clatter of new jack swing. Getting Bobby Brown, the king of new jack swing, on the single was a major coup. Ian Prince co-produced “She Ain’t Worth It” with Denny Diante, a former Columbia exec who’d just become vice president of A&R at MCA, and the song definitely sounds like a white record exec telling a drum programmer to make a new jack swing record. (Ian Prince didn’t do anything big after “She Ain’t Worth It, but Antonina Armato stuck around, later doing a lot of work with teenage stars like Miley Cyrus and Selena Gomez. Armato co-wrote a #1 hit last year, so she’ll be in this column again.)
“She Ain’t Worth It” fits into an ancient pop-song category: the track where one guy warns another guy not to get involved with a girl. Medeiros sings that this particular unnamed girl just got an attitude; she leads you on and leaves you blue. The lyrics are simplistic and extremely basic, and they don’t seem to describe an actual human being. Instead, they exist in the realm of pure cliché: “One day, she’ll treat you nice/ Then she turn as cold as ice.” The lyrics aren’t even interesting enough to read as actual misogyny. At one point, Medeiros mentions that he’s been through all of this with her, so this is all jealous-ex stuff.
When Bobby Brown shows up, he pretty much reiterates everything that Glenn Medeiros just said: “The girl’s jazzy, but she’s nothing but trouble.” (It’s a shame that “jazzy” never caught on. That’s a fun word.) When he opens his verse, though, Brown reveals something about his own dating habits: “One thing I hate is when a girl plays fake and tries to make me late for another date.” That makes Bobby Brown sound like a sitcom teenager, trying to juggle two dates at once. I have never had this problem, but sitcoms have taught me that it never works out. The girls eventually find out, and they inevitably realize that he ain’t worth it.
The Bobby Brown verse on “She Ain’t Worth It” is supremely goofy, but it’s the one moment where the song really crackles to life. Brown might not be a rapper, but he’s got serious charisma, and he’s got the confidence to deliver those ridiculous lines. Glenn Medeiros is another story. I really like new jack swing in general, and “She Ain’t Worth It” isn’t an offensive version of the sound or anything. But when you compare it to the music that Bobby Brown was making on his own, “She Ain’t Worth It” is thin and forgettable. Medeiros is a big blank at the center of the song. There’s nothing technically wrong with his vocal, but it’s got no excitement or charisma or conviction. He could be anyone.
Glenn Medeiros never got anywhere near the top 10 again after “She Ain’t Worth It.” He followed the single with “All I’m Missing Is You,” a collaboration with former Number Ones artist Ray Parker, Jr., and that song peaked at #32. In 1991, Medeiros recorded the title song for the Richard Grieco movie If Looks Could Kill, but that didn’t do much for either him or Grieco. Eventually, Medeiros went back to Hawaii and became a history teacher, then a vice principal. Later, Medeiros earned his doctorate and became the head of a private school in Honolulu. He apparently also hosts a luau at a hotel in Waikiki. I wonder how often Medeiros tells the kids in his school about his time as a teen-idol pop star.
Bobby Brown’s career went a different route. Brown married Whitney Houston in 1991, when he was 22 and she was 27. This did not turn out well for either of them. Brown was abusive, and both he and Houston spiraled into addiction. Houston maintained her pop stardom for a long time, but Brown’s was more fleeting. Brown didn’t follow up Don’t Be Cruel until 1992, when he finally released his album Bobby. Lead single “Humpin’ Around,” which still gets stuck in my head all the time for no reason, peaked at #3. (It’s a 7.) Follow-up single “Good Enough,” which peaked at #7, was Brown’s last top-10 hit. (It’s another 7.) Bobby sold two million copies, less than a third of what Don’t Be Cruel had done.
In the early ’90s, Brown collaborated with the other former members of New Edition on a few tracks. In 1996, New Edition got back together and released the reunion album Home. Brown was in a bad way at the time, and he only sang on a couple of the tracks from the album, but one of those tracks was the single “Hit Me Off,” which peaked at #3. That’s the highest that any New Edition track has ever charted. (It’s a 7.)
The New Edition reunion tour went badly. All the members of the group had their own solo sets. One night, Brown wouldn’t get offstage. Brown and Michael Bivins got into a fistfight onstage, which turned into a brawl between their security people backstage. Brown left the tour and the group, and his career languished for years. He almost signed with Death Row just as that label was falling apart. He did sign with Murder Inc., just as that label was falling apart. He got arrested again and again — spousal abuse, drunk driving, nonpayment of child support. In 2005, Brown and Whitney Houston appeared in a single season of the Bravo reality series Being Bobby Brown, an infamous trainwreck that mostly made it clear that these two people were not living healthy lives. People made a lot of jokes about that show at the time. In retrospect, it’s just profoundly sad.
Brown and Houston divorced in 2007, and when Houston died, a lot of the people close to her blamed her addictions on Brown. Brown has suffered more terrible losses in the year since; two of his children, daughter Bobbi Kristina and son Bobby Jr., both died very young. But Bobby Brown is still working. He’s done a few more New Edition reunions and a few more reality shows. Earlier this year, he was on The Masked Singer. He’s remained in the public eye.
I love a lot of Bobby Brown’s music, but at this point, I’d rather be Glenn Medeiros than Bobby Brown. It’s an old story. More often than not, the transcendent stars are self-destructive monsters who bring misery to themselves and everyone around them, while the forgotten mediocrities turn out to be decent people with real lives. That’s rock ‘n’ roll, baby. Neither Glenn Medeiros nor Bobby Brown will appear in this column again.
BONUS BEATS: “She Ain’t Worth It” has not lingered in popular culture at all. There are no prominent covers, no big remixes, no soundtrack appearances that I can find. The song has just disappeared into the ether. So instead, let’s go to the extreme other end of the Bobby Brown featured-artist timeline. The last time Brown had a prominent appearance on another artist’s single, it was on Ja Rule’s 2002 track “Thug Lovin’.” In that song’s video, Bobby Brown wears a Len Bias jersey. He also exits a helicopter by jump-kicking and then humping the air. Here’s that video:
(“Thug Lovin'” peaked at #42. Ja Rule will eventually appear in this column.)
THE NUMBER TWOS: En Vogue’s elegantly layered, deeply funky debut single “Hold On” peaked at #2 behind “She Ain’t Worth It.” It’s a 9.