Special Report

25 Bizarre Musical Collaborations

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A love of music can transcend genre boundaries and draw together all sorts of talented musicians who otherwise would never be seen or heard sharing a stage or a recording studio. Sometimes these collaborations make perfect sense, and other times they’re real head-scratchers.

To assemble a list of 25 particularly unlikely — in fact, bizarre — musical collaborations, 24/7 Tempo reviewed lists of curious pairings appearing on a wide range of general interest, culture, and music websites, including Rolling Stone, NME, BuzzFeed, The CheatSheetOpen CultureRiot Fest, Copper, Radio X, The Whisp, ListVerse, and Digital Spy.

There are a lot of reasons for musicians to collaborate. Crossovers can give artists the opportunity to experiment with their sound and explore new styles. They can also make headlines and draw in new fans and listeners. See, for instance, these top musical collaborations that hit No. 1.

One of the most common kinds of musical collaboration in recent years has been the appearance of hip-hop artists on country songs — the most famous, though hardly the first, example of which is “Old Town Road,” the megahit by Lil Nas X and Billy Ray Cyrus. But classical musicians sometimes like to work with rock or jazz performers, and old-school pop singers have had success doing duets with their modern-day equivalents. (These are the 25 most iconic musical duos of all time.)

Click here to see 25 bizarre musical collaborations

If you seek out some of the recordings listed here, chances are that sometimes you’ll end up asking yourself what the participants could have been thinking — but other times, maybe the majority, you’ll be pleasantly surprised at how well disparate musical talents can mesh. 

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Andrea Bocelli and Dua Lipa
> Song: If Only

Andrea Bocelli is an opera singer and master of multiple instruments. Dua Lipa is known for her big pop dance hits that have propelled her into stardom in recent years. The two team up for a slow and heartfelt ballad. The song is different from most of Lipa’s music and it shows that she can certainly sing and has more range than some would give her credit for.

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Beyoncé and the Dixie Chicks
> Song: Daddy Lessons

Beyoncé‘s 2016 mega album “Lemonade” included a collaboration with country pop group the Dixie Chicks. Beyoncé sings over the twang of a banjo and the women share their differing experiences growing up in Texas. The collaboration shows a new side of Beyoncé and is a good demonstration of her skills as a songwriter.

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Bob Dylan and Kurtis Blow
> Song: Street Rock

Kurtis Blow was one of hip-hop’s early pioneers in the 1980s and Bob Dylan was a pioneer of a lot of things in his heyday. While Dylan is known for spanning a lot of genres — and while he and Blow are both known for strong anti-establishment lyrics despite their differing styles — have you ever heard him rap? “Street Rock” treats us to a little of just that.

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David Bowie and Bing Crosby
> Song: Little Drummer Boy (TV appearance)

Bowie and Crosby teamed up for an intergenerational performance of this Christmas classic on Crosby’s 1977 Christmas TV special on CBS. Bowie was rumored to have partly taken the gig because his mom was a big Bing Crosby fan. While the song is a bit more of Bing Crosby’s style, Bowie showed that he could perform traditional music as well as his more signature stuff. (Crosby died just a month after the show was taped, and never saw the results of the collaboration.)

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Eminem and Bon Iver
> Song: Fall

Eminem, long considered to be the preeminent white rapper, is known for some angry and often pain-filled lyrics. Justin Vernon’s indie folk band Bon Iver is also known for emotional lyrics, but with a very different tone and delivery. Here, Bon Iver provides background vocals as Eminem expresses his problems with the music industry and the pressure and criticism he has endured since the debut of his biggest albums.

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Frank Sinatra and Elvis Presley
> Song: Witchcraft/Love Me Tender

In 1960, ABC aired “The Frank Sinatra Timex Special: Welcome Home Elvis,” to celebrate the return of Presley from his military service in West Germany. As part of the program, the two sang a medley of one of Sinatra’s biggest hits and one of Presley’s, trading verses. Women in the audience crazy screaming whenever Elvis opened his mouth, attesting to his massive popularity at the time. In Sinatra’s own early days of stardom, women did the same for him.

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Herbie Hancock and Trey Anastasio
> Song: Gelo No Montanha

In 2005, Hancock released his 45th studio album, “Possibilities,” featuring a range of pop artists including John Mayer, Christina Aguilera, Paul Simon, Sting — and the leader of psychedelic jam band Phish, Trey Anastasio. Their track, whose title is Portuguese for “Ice on the Mountain, a ballad featuring Anastasio’s guitar, won a Grammy nomination for Best Pop Instrumental Performance.

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Iggy Pop and Ke$ha
> Song: Dirty Love

Iggy Pop has always been known for an experimental style and for rocking the boat. Labeled the Godfather of Punk, he founded the influential band The Stooges and collaborated with David Bowie in West Berlin in the 1970s. Singer and rapper Ke$ha had numerous Billboard Hot 100 hits in the 2010s that would still be a hit with the right crowd today. She brought Iggy on to her third studio album, “Warrior,” to record this track for an exciting mix of genres.

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John Cale and Terry Riley
> Song: Church of Anthrax (album)

John Cale was a founding member of the Velvet Underground and Terry Riley is a composer best known for his minimalist works. The two combined their talents for this mostly instrumental art-rock album. Riley plays keyboards and soprano saxophone, while Cale handles keyboards and various string instruments.

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Lil Nas X and Billy Ray Cyrus
> Song: Old Town Road

The track that holds the record for longest amount of time ever in the No. 1 slot on Billboard’s Hot 100, “Old Town Road” was a sensation, combining country and hip-hop for a unique sound. When the track met resistance from the conventional country music world, Cyrus — father of Miley Cyrus and known for his 1992 country megahit “Achy Breaky Heart” — jumped on the remix to give the song unmistakable country credibility The song was remixed several more times with Young Thug, Mason Ramsey, and BTS, and launched Lil Nas X’s flourishing music career.

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Lou Reed and Metallica
> Song: Lulu (album)

Lou Reed of the Velvet Underground and Metallica made an entire album together, released in 2011. It was the final studio album for Reed before his death in 2013. Reed is known for his laid-back deadpan singing style, which contrasted with Metallica’s intense, in-your-face heavy metal musil. Critically the album didn’t do great, but it definitely has a unique sound.

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Louis Armstrong and Jimmie Rodgers
> Song: Standing on the Corner (Blue Yodel No. 9)

Many decades before collaborations between white country and Black rap or R&B musicians became commonplace, jazz legend Louis Armstrong lent his trumpet (and his wife, Lil Armstrong, her piano) to this bluesy song by the so-called “father of country music,” Jimmie Rodgers, known for his yodeling as well as his singing.

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Metallica and Lang Lang
> Song: One

The second time Metallica makes this list, this time collaborating with world renowned concert pianist Lang Lang. In their live performance in Beijing, China, the pianist meshes nicely with the band’s energetic musical style for this searing anti-war song. Lang has performed with a range of musicians, often with some of the world’s top philharmonic orchestras, but has also worked in more popular contexts, like collaborating with Mike (“Tubular Bells”) Oldfield on an album and tracks for the “Gran Turismo 5” video game.

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Mick Jagger and The Chieftains
> Song: The Long Black Veil

The Chieftains are a traditional Irish band formed in Dublin in the 1960s, often credited with helping popularize Irish music around the world. While they are among the leading exponents of Irish musical tradition, they have also recorded with a vast range of pop, country, and rock musicians, among them Jackson Brown, Madonna, Van Morrison, and Willie Nelson. One of their most successful tracks, from the album of the same name, was this 1959 country classic, with Jagger in full country mode.

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Paul McCartney and Michael Jackson
> Song: Say Say Say

Two of the biggest musical names of all time created “Say Say Say” in 1983. Michael Jackson was in the prime of his career and Paul McCartney was continuing to make music years after the breakup of the Beatles. As a result of this collaboration, Jackson learned that McCartney owned a lot of music from other artists’ catalogues and was making money from it. Ironically, Jackson would then go on to outbid McCartney for the Beatles’ catalogue in 1985.

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Run-DMC and Aerosmith
> Song: Walk This Way

In this landmark of early hip-hop-mainstream crossover, Aerosmith brought in Run-DMC to remix their hit song. In the music video, a mock conflict between the two sides seems to be brewing, but the barrier between the two is quite literally broken down and ends with the bands performing together. Run-DMC raps some of Aerosmith’s lyrics and then everyone jams out together.

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Slash and Fergie
> Song: Sweet Child o’ Mine

Slash originally found fame and success with Guns N’ Roses and Fergie with the Black Eyed Peas. Fergie went solo after several big hits with the Black Eyed Peas and Slash branched out for some solo work as well. They have collaborated several times including their song “Beautiful Dangerous” as well as a live performance of “Sweet Child o’ Mine.”

English: Distributed by Impulse! Records and ABC/Dunhill Records. Photographer uncredited on the publicity photo itself; most likely Francis Ing, who is credited for the photography on Astro Black (see Discogs link above)., Public domain, via Wikimedia Commons

Sun Ra and The Blues Project
> Song: Batman and Robin (album)

One of the unlikeliest of all musical collaborations is this one, featuring avant-garde Afro-futurist pianist and bandleader Sun Ra and members of his Arkestra and prolific rock and blues musician and producer Al Kooper’s group The Blues Project. This album, intended for children, and designed to cash in on the popular ’60s-era “Batman” TV series was originally credited to “The Sensational Guitars of Dan and Dale” for contractual reasons, but later released with the names of the actual performers. The music is original and not from the series, and much of it was based on classical works in the public domain.

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Photograph by Greg Gorman / Wikimedia Commons / Public Domain

Tom Waits and the Kronos Quartet
> Song: Tom Waits and the Kronos Quartet Live (concert and album)

Tom Waits was popular in the 70s and 80s for his blues and jazz music that often focused on the underbelly of society. The Kronos Quartet is a string ensemble out of San Francisco founded over 40 years ago and known not only for performing contemporary classical music but for collaborations with everyone from Björk to the Modern Jazz Quartet to the Mexican alternative band Café Tacuba. Waits and the quartet collaborated in a concert to raise money and promote peace. The concert also had performances by Tibet’s Gyuto Choir and India’s Anoushka Shankar.

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Tony Bennett and John Mayer
> Song: One for My Baby

Tony Bennett is a legendary singer of traditional pop standards, jazz, and show tunes. He is known for collaborating with many modern artists and continues to be active at the age of 95, and despite a diagnosis of Alzheimer’s disease. John Mayer has produced countless albums and is well known for his vocals as well as ability on the guitar. The two sing this Johnny Mercer-Harold Arlen standard, made famous by Frank Sinatra, on Bennett’s “Duets II” album. The album features several other great performances with artists like Amy Winehouse, Willie Nelson, and Mariah Carey.

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Trace Adkins, Stevie Wonder, and Keb’ Mo
> Song: Memory to Memphis

Trace Adkins is a country musician who’s been active for almost 40 years. Keb’ Mo’ is known for his own original style of postmodern blues. And Stevie Wonder is, well, Stevie Wonder — one of the great and most versatile musical talents of our age. “Memory to Memphis” is sung by Adkins with Keb’ Mo on guitar and Wonder on harmonica.

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“Weird Al” Yankovic and Kate Winslet
> Song: I Need a Nap

Yankovic is known for his parodies of popular songs and for creating wacky new ones of his own. Winslet is known for her acting career, encompassing everything from “Titanic” to “Mare of Eastown.” She and Yankovic sing this song from the CD accompanying Sandra Boynton’s book “Dog Train: A Wild Ride on the rock-and-Roll Side.” While musically it may not be the most astounding work, “I Need a Nap” focuses on a message that we can all get on board with.

Anthony Quintano / Wikimedia Commons

Willie Nelson and Wynton Marsalis
> Song: Two Men With the Blues (album)

Willie Nelson, one of the originators of “outlaw country” and both an actor and an activist, is famous for long hair, weed, and a disdain for authority. Wynton Marsalis is a jazz legend who has won just about every accolade a musician can, including the first Pulitzer Prize in Music given to a jazz musician. The two teamed up to create an entire album that combines both of their unique styles on a range of blues, country, and pop songs. Marsalis even sings a bit.

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Yo Yo Ma and Elmo
> Song: Elmo’s fiddle lesson, Sesame Street (TV appearance)

Two icons came together to make music for the entire family when cello legend Yo Yo Ma — who has appeared on “Sesame Street” numerous times to help inspire the younger generations to take up music — tried to teach Elmo how to play the fiddle while showing off a little of his own talents.

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