10 Times Popular Singers Made a Terrible Song Choice

Welcome to WatchMojo and today we’re counting down our picks for the songs by famous pop stars that were anything but a perfect match for their talents.

#10: “Hey You” (2007)

Madonna
Madonna became the “Queen of Pop” due to her reputation as a trendsetter. If there was ever a song that didn’t have a whiff of the Material Girl’s audacity, originality, or taste. It’s “Hey You.” “”Hey You” is a collaboration between Madonna and Pharrell Williams, but not exactly one that will get the dance floor popping. Instead, it’s a charity single ballad for the Live Earth benefit concerts. And the lyrics are mostly generic platitudes about staying positive. It's clearly well-intentioned, but that’s about the best we can say about it. While some singers can pull off this kind of achingly sincere lyricism, Madonna’s attempt just doesn’t click.

#9: “Yummy” (2020)

Justin Bieber
Food-as-sex metaphors are a tricky gambit for pop stars. If they miss the mark, what should be enticing can just become unappetizing - in multiple ways. That’s what happened with this Justin Bieber song. “Yummy” sees the pop superstar making what he may have intended as a bedroom jam. But any attempt at finding intimacy is ruined by the lyrics, which are ridiculous to begin with, as well as Bieber’s inability to make them remotely work. We’re not sure if anyone could pull off a chorus like “Yeah, you got that yummy-yum.” But it sure ain’t the Biebs. Of course, he’s not alone with this kind of misfire. A few years prior, Katy Perry released the undercooked misfire “Bon Appetit.” Can you say “yuck”?

#8:”Sometimes” (1999)

Britney Spears
Britney Spears’ debut single is so iconic that we don’t need to even bother with naming it. But can you name her follow-up single, from the very same album? “Sometimes,” an upbeat ballad about uncertainty in love, isn’t unlistenable. But it’s generic in a way that her previous single decidedly was not. Neither the lyrics nor the production give her much to work with, and Spears’ performance lacks the “wow” that made her a star right out of the gate. If you watch the music video, the charisma is clearly there. But it doesn’t make this song any less forgettable. Fortunately, there would be plenty more iconic singles to come.

#7: “Wooden Heart” (1961)

Elvis Presley
While many of the songs recorded by the "King of Rock 'n' Roll” have remained pop culture staples decades later, others have not. “Wooden Heart,” featured in “G.I. Blues,” is in the latter category. Based on a German folk song, it’s a polka-ish song that finds Presley crooning corny platitudes over an accordion-led instrumental, with some German in the mix towards the end. Despite being barely over two minutes, it’s not a breezy listen. The rebellious energy of his best songs is all but absent. Strangely, while Presley’s version topped the charts in numerous countries, he didn’t release it as a single in the U.S. Instead, pop singer Joe Dowell tackled it, with his version - which isn’t exactly an improvement - hitting number one.

#6: “Jewels n’ Drugs” (2013)

Lady Gaga feat. T.I., Too Short & Twista
Among Lady Gaga fans, her third album, “Artpop” has a somewhat complicated legacy, including a collaboration with disgraced singer R. Kelly that was later removed from streaming and future editions. Though Gaga had established herself as someone who wasn’t afraid to try new things, it didn’t always work out like she intended. Perhaps the best instance of this is the song “Jewels n’ Drugs,” which sees Gaga teaming up with an impressive lineup of rappers: T.I., Too Short, and Twista. But while the MCs all deliver quality performances, Gaga herself seems completely lost in her own song, with limp contributions It’s the unfortunate case of a star attraction not knowing how to work as a supporting player.

#5: “Keeps Gettin' Better” (2008)

Christina Aguilera
Speaking of Lady Gaga, as the 2000s winded down, Christina Aguilera made a shift towards electropop, a move seen by many as her trying to replicate then-rising star Gaga’s success. The earliest instance of this was “Keeps Gettin’ Better,” first released as part of a greatest hits compilation of the same name. But it did not enter the pantheon of Aguilera classics like “Genie in a Bottle” or “Beautiful.” Her stunning vocal range is inhibited by thumping programmed drums and robotic synths. Aguilera cited English synth-pop duo Goldfrapp as an inspiration. But the resemblance between it and their song “Ooh La La” was uncanny enough for it to seem like a pretty blatant ripoff. By trying to stay trendy, Aguilera completely missed the mark.

#4: “End Game” (2017)

Taylor Swift feat. Ed Sheeran & Future
There’s no question that Taylor Swift’s “Reputation” era was an interesting one. But was it a successful one? While it was the best-selling album of 2017 and still has plenty of supporters, some felt Swift was taking her sound in an incompatible direction. Perhaps the clearest example of this is “End Game,” a strange foray into trap-inspired pop rap and R&B. While the lyrics are about undying devotion to another, they’re overshadowed by how out of place Swift sounds on her own track, especially when juxtaposed with a verse from Future. Meanwhile, Ed Sheeran’s verse is another aspect of this track that could be charitably described as a “failed experiment.” Fortunately, Swift didn’t stay on this course.

#3: “My Name Is Not Susan” (1991)

Whitney Houston
Technical prowess is crucial to being a great singer. But it’s not the only part. What made so many of Whitney Houston’s best songs so good isn’t just how well she hit the notes but also how convincingly she conveyed every emotion. “My Name Is Not Susan,” from her album “I’m Your Baby Tonight,” sees Houston trying to shake up image by adapting to the new jack swing sounds of the era. The problem mainly lies in the lyrical content. Houston sings as a woman admonishing a partner who misnames her in bed. Her voice sounds as good as ever, but it feels like she’s trying to sound angry instead of embodying it. Her name is not Susan, and this is not one of her better-remembered songs.

#2: “Treat Her Like a Lady” (1999)

Celine Dion
On the one hand, it makes sense that a vocalist as captivating as Celine Dion would want to branch out. On the other hand, there’s a reason why no one associates Dion with reggae or dancehall. If you’re skeptical about how well that could work, just listen to 10 seconds of “Treat Her Like a Lady” for a clear answer. A cover of Jamaican singer Diana King's song, it has Dion making an ill-fated attempt at funk-filled female empowerment, completely with smoky vocals and howls that don’t fit her vibe, to say the least. Points for trying, though.

#1: “Whatzupwitu” (1993)

Eddie Murphy feat. Michael Jackson
Seeing the King of Pop as a featured artist in the early 90s is unexpected. Even more surprising is that the main artist is Eddie Murphy. The comedy superstar had an attempt at a music career that never exactly took off. On his third and final album, he enlisted the help of Jackson, a move that likely seemed a surefire way to create a hit. A befuddling mishmash of overproduction, Murphy half-heartedly singing half-baked lyrics about nature and humanity, and Jackson belting the chorus question ad nauseam, “Whatzupwitu” sees two of the biggest icons of the previous decade coming together for a song that’s truly inexplicable. It would be a mess no matter what, but Jackson’s appearance further underlines the “WTF” of “Whatzupwitu”.



What singer/song match do you think was a flop? Let us know in the comments!