Top 10 Cringiest Celebrity Duets

#10: “Booty” (2014)

Jennifer Lopez feat. Iggy Azalea

It sounds like a parody, but somehow it’s not. This song from Lopez’s album “A.K.A.” is a very straightforward dance track written by multiple artists, including Chris Brown and Pitbull. This makes the repetitious and rhymeless lyrics even more strange - and the male gaze-y aspect is disturbing. With its clichéd Middle Eastern flavor and generic rhythm, you might hope Iggy Azalea’s involvement would help - oh, but no. Azalea’s verse repeats the same idea as the rest of the song. At least she and Lopez look good, and the song was a modest hit, but there is a reason why Lopez was so reluctant to record it in the first place.

#9: “Dooo It!” (2015)

Miley Cyrus & The Flaming Lips

Cyrus has been known for her controversial performances, especially her salacious rendition of “Blurred Lines” with Robin Thicke at the 2013 MTV Video Music Awards. But in terms of cringe, this collaboration with rock band The Flaming Lips takes the cake. The original hip hop song about loving peace and smoking marijuana is nothing special. It even comes with a nigh-unwatchable music video. At the 2015 MTV VMAs, though, The Flaming Lips got involved, which added further insult to injury. Add in the random drag queens from “RuPaul’s Drag Race,” and you get a very puzzling display indeed. Let’s not.

#8: “TROLLZ” (2020)

6ix9ine & Nicki Minaj

Following the rapper’s release of the garishly awful “Gooba” after his stint from prison, 6ix9ine upped the ante with this song. This time, however, Nicki Minaj would sing and contribute a verse. With the same M&M-style colors, “TROLLZ” is a dull rote rap trap track with the usual self-aggrandizing clichés and digs at other rappers. Yawn, but also…no. Minaj’s two verses don't make matters any better, sounding bland and lazily-written. Minaj comes across as lethargic and even bored. Perhaps having to perform without her signature machine gun fire rapping style killed her buzz. Whatever the case, these two are not lit.

#7: “The View” (2011)

Lou Reed & Metallica

This songwriter’s last single is a disappointing one. Reed’s flat talk-sing delivery paired with Metallica’s heavy metal flair is an unsuccessful juxtaposition almost painful to listen to. The black-and-white music video, directed by Darren Aronofsky of all people, fails to justify the song. Although some critics gave the collaboration positive reviews, perhaps because of its riddling but eloquent lyrics, the fans were not as pleased. Unfortunately Reed died in 2013, so this single will just have to be his last word. As it is, this duet mostly repels us, and Metallica should not have gone there.

#6: “Sweet Child O’ Mine” (2011)

Fergie & Slash

Watching the Super Bowl halftime show had never been so painful. For the 2011 show, members of the Black Eyed Peas were invited to perform, with Guns N’ Roses guitarist Slash as a special guest. During the show, Fergie and Slash performed “Sweet Child O’ Mine.” We say performed, but it was really Fergie singing a very warbly rendition and dancing sensuously while Slash stood stoically playing guitar. If there is such a thing as negative chemistry, these two had it. The halftime show in general got negative reviews all around, but Fergie and Slash’s “duet” was certainly a low point.

#5: “Walk This Way” (2001)

Aerosmith, N’Sync & Britney Spears

Speaking of embarrassing Super Bowl halftime shows, we’d be remiss if we didn’t talk about this chaotic motley. In 2001, Aerosmith and NSYNC headlined the show with a guest appearance by the Princess of Pop herself. At the end of the medley, Spears joined NSYNC and Aerosmith in singing the latter’s “Walk This Way,” joined by Nelly and Mary J. Blige. It’s a blast from the past, all right, but it’s also a mess of genres that never really cohere. Spears especially looks out of place with the rock bands and the rap artists. Perhaps this is a bit of nostalgia we’ll just not partake in.

#4: “Sweet Lovin’ Friends” (1984)

Dolly Parton & Sylvester Stallone

You heard right. We’re not sure who was the one to suggest pairing these two together, but they were undoubtedly wrong. The film was a flop, and offering Dolly Parton and Sylvester Stallone in a duet is one reason why. Stallone is no singer, much less a country one, and he is woefully outclassed by Parton in his cotton-mouthed rendition of this original song. Even Parton is not at her best here. The song was nominated for a Golden Raspberry Award for Worst Original Song and the film in general was nominated for Worst Musical. What a mismatch.

#3: “Do What U Want” (2013)

Lady Gaga feat. R. Kelly

We’re not happy these two did what they wanted. A synth-pop, R&B-infused number written by Gaga, the song insists that the world can only have the singer’s body, and not her thoughts and opinions. When she performed it at the American Music Awards, seeing a breathy-voiced secretary Gaga singing “Do what you want with my body” to R. Kelly was stomach-curdling on its own. It became even more so over time as more and more assault allegations about Kelly became common knowledge. Gaga ended up pulling the song from music streaming services, which is a good call.

#2: “Strut” (2004)

Steven Seagal feat. Lady Saw

Now this was an odd pair indeed. Controversial actor Steven Seagal actually co-wrote this song with Jamaican singer Lady Saw in one of the most unexpected duets in music. Seagal’s melodic part and his voice contrast sharply with Saw’s aggressive rap creating a very jarring effect. Also known as “Me Want The Punani” due to the repeated phrase, listeners were not happy with Seagal’s fake Jamaican accent. The witless lyrics failed to redeem the song, either. Why this action film star would even try his hand at dancehall is a mystery for the ages. Talk about cringe.

#1: “Accidental Racist” (2013)

Brad Paisley & LL Cool J

This country song stirred quite a lot of controversy with its tone-deaf lyrics defending wearing a t-shirt of the Confederate flag as Southern pride. Yeah. Even more confusingly, Paisley co-wrote the song with rapper LL Cool J. This means we get to hear Paisley’s earnest country ballad vocals along with LL Cool J’s rap. It’s hard to tell which is worse, Paisley’s uneasy lines or LL Cool J earnestly rapping, “If you don't judge my durag, / I won’t judge your red flag.” Those are red flag lyrics, all right. Paisley and LL Cool J were obliged to explain the meaning of their song, which is not a good sign at all, to the embarrassment of all of us. Now this is cringe.

Which other mismatched musical duet made you shrivel up inside hearing or watching it? Let us know in the comments down below!