Special Report

25 Bizarre Musical Collaborations

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Atlanta-based rapper Lil Nas X had an unexpected hit with “Old Town Road” — a sub-two minute rap song that gained widespread popularity on social media platforms. Perhaps even more unexpected was the subsequent remix of the track featuring a verse from “Achy Breaky Heart” by country singer Billy Ray Cyrus, the man behind one of the most popular country albums of all time.

It wasn’t long before the single reached No. 1 on the Billboard Hot 100.

Popular music has a history of unexpected bedfellows. Musicians often team up to reach potentially new fans, especially if the artist they’re partnering with works in a different genre. They may also simply be a fan of one another’s work and desire the opportunity to collaborate on a creative process.

Some of the world’s most famous musicians — including Michael Jackson, Taylor Swift, and Elton John — have taken part in unexpected musical alliances. Frequently, it’s to record a single track, but sometimes artists ultimately produce an entire album of work together. With all of the talent involved, it’s no surprise that many of these collaborations were highly successful, obtaining critical and commercial success. Some, however, were less fortunate.

Click here to see 25 of the most bizarre musical collaborations.

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1. Aerosmith and Run-DMC
> Collaboration: Walk This Way
> Year: 1986

When Boston-based hard rockers Aerosmith hooked up with Run-DMC, the rappers from Queens, for the cover of the Aerosmith song “Walk This Way,” it made musical history. The collaboration lifted Aerosmith out of a slump and helped mainstream the career of Run-DMC. The video of the two acts rehearsing in adjacent studios that shows Aerosmith frontman Steven Tyler busting through the wall symbolizes the breaking down of boundaries between musical genres.

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2. Alice in Chains and Elton John
> Collaboration: Black Gives Way To Blue
> Year: 2009

Alice in Chains was among the most popular “grunge” bands of the 1990s. The group met with tragedy when lead singer Layne Staley died of a drug overdose in 2002. Seven years later, the remaining members teamed up with Sir Elton John — who lent his piano playing skills — to record the song “Black Gives Way to Blue” in tribute to Staley.

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3. Alicia Keys and Jack White
> Collaboration: Another Way To Die
> Year: 2008

R&B singer/songwriter Alicia Keys and accomplished rock-and-roller Jack White teamed up in 2008 to record the duet “Another Way to Die” for the James Bond film “Quantum of Solace.” Unfortunately, the track was blasted by many critics for being a jumbled mess.

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4. Anthrax and Public Enemy
> Collaboration: Bring the Noise
> Year: 1991

The unlikely collaboration between heavy metal headbangers Anthrax and hip-hop act Public Enemy for the song “Bring the Noise” became the subject of a Smithsonian Museum of American History mini-documentary in its Places of (Musical) Invention video series. The collaboration led to a joint tour, and each show ended with Public Enemy and Anthrax on stage performing the song.

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5. Bone Thugs-n-Harmony and Phil Collins
> Collaboration: Home
> Year: 2003

Many hip-hop artists sample a wide variety of music. The relationship between Cleveland rap group Bone Thugs-n-Harmony and English musician Phil Collins goes even deeper, however. After using Collins’ “Take Me Home” as the basis for their song “Home,” Bone Thugs flew to Switzerland to meet with Collins, shot a music video together, and inducted Collins into the group as an honorary member, bestowing upon him the nickname “Chrome Bone.”

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6. Brad Paisley and LL Cool J
> Collaboration: Accidental Racist
> Year: 2013

Country artist Brad Paisley and rapper LL Cool J joined forces in 2013 to record the song “Accidental Racist.” Around the time of its release, Paisley told USA Today that the song, which deals with race-related issues, was meant to spark discussion. Paisley also appeared on LL Cool J’s single “Live for You,” released that same year.

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7. Bryan Adams and Jennifer Lopez
> Collaboration: That’s How Strong Our Love Is
> Year: 2019

Canadian rocker Bryan Adams had already recorded “That’s How Strong Our Love Is” for the album “Shine the Light,” but felt the song needed something more. Adams had met the multi-talented Jennifer Lopez in Spain years before, and he wanted her to collaborate on the song. He called her manager and requested that she sing on the song, and she agreed.

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8. Celine Dion and R. Kelly
> Collaboration: I’m Your Angel
> Year: 1998

Long before R. Kelly’s publicized allegations of sexual misconduct, he and Celine Dion collaborated on the single “I’m Your Angel” that vaulted to the top of the Billboard Hot 100 chart. The song was nominated for Best Pop Collaboration With Vocals at the 1999 Grammy Awards. Following a documentary about the allegations against Kelly, Dion has removed the song from streaming services earlier this year.

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9. Ed Sheeran and Andrea Bocelli
> Collaboration: Perfect Symphony
> Year: 2017

British pop star Ed Sheeran wanted an operatic tone to his song “Perfect,” and he wanted Italian tenor Andrea Bocelli to provide it. It helped that Bocelli’s sons were big fans of Sheeran’s. So Sheeran flew to Bocelli’s home in Tuscany, Italy, last year, and the two recorded the track for Sheeran’s album “Divide.”

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10. Eddie Murphy and Michael Jackson
> Collaboration: Whatzupwitu
> Year: 1993

Eddie Murphy and Michael Jackson, who could do no wrong in movies and music in the 1980s, had already collaborated on the music video for Jackson’s song “Remember the Time” in 1992 before they teamed up to record “Whatzupwitu.” Jackson was interested in doing the song because of its positive message. The song, however, was a rare misfire for Jackson. “Whatzupwitu” rose to No. 74 on the Billboard Hot R&B/Hip-Hop Songs chart, and its music video is regarded as one of the worst ever.

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11. Eminem and Bon Iver
> Collaboration: Fall
> Year: 2018

Some musicians are less enthusiastic about their collaborations than others. Indie crooner Justin Vernon of Bon Iver fame publicly denounced the Eminem song “Fall,” which features his vocals and for which he’s listed as a co-writer. Vernon claims not to have been in the studio when Eminem recorded the lyrics for the song — which include a homophobic slur — and that he asked that the track be changed upon hearing it.

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12. Janet Jackson and Cliff Richard
> Collaboration: Two To The Power Of Love
> Year: 1984

Pop diva Janet Jackson and creaky British rocker Cliff Richard formed an unlikely duo to record the forgettable “Two To The Power Of Love” in 1984. For Jackson, 18 years old at the time, the song marked her first chart appearance. She would go on to record 10 No. 1 hits.

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13. Jay-Z and Linkin Park
> Collaboration: Collision Course
> Year: 2004

This celebrated mini-album mashup of music genres worked because of the artists’ mutual respect. The collaboration brought together hip-hop performer Jay-Z, who already had eight No. 1 albums, and rockers Linkin Park, authors of diamond-certified “Hybrid Theory.” The “Collision Course” pairing debuted at No. 1, went platinum, and produced a top 20 Hot 100 hit in “Numb”/”Encore” that won Best Rap/Sung Collaboration at the 2005 Grammy Awards.

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14. Justin Bieber and Busta Rhymes
> Collaboration: Drummer Boy
> Year: 2011

Canadian tween heartthrob Justin Bieber teamed with rapper/record producer Busta Rhymes for the remake of the Christmas chestnut “Drummer Boy” for Beiber’s first Christmas album, “Under the Mistletoe,” in 2011. The album also included pairings with Mariah Carey, Boyz II Men, and Usher.

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15. Kiss and Michael Bolton
> Collaboration: Forever
> Year: 1990

Aside from the single “Beth,” Kiss’s most successful single on the pop charts was “Forever,” a song co-written by soft-rock crooner Michael Bolton. “Forever” peaked at No. 8 on the Hot 100 for the New York City-based glam metal band. Bolton was no stranger to hard rock; in 1983, he auditioned for British metal group Black Sabbath.

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16. Lil Nas X and Billy Ray Cyrus
> Collaboration: Old Town Road
> Year: 2019

Rapper Lil Nas X’s western-themed rap song “Old Town Road” initially charted on Billboard’s country charts but was removed for not being sufficiently “country.” Billy Ray Cyrus attempted to fix this by appearing on a remix of the track. It’s not Cyrus’s first time collaborating with a hip-hop artist, having worked with rapper Buck 22 on a remix of his 1992 hit song titled “Achy Breaky Heart 2.”

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17. Lou Reed and Metallica
> Collaboration: Lulu
> Year: 2011

Critics are divided when it comes to this full-length album made by the late art rocker Lou Reed and metal legends Metallica. The 77 minute-long record is dark, grueling, and far from either act’s most accessible work.

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18. Michael Jackson and Eddie Van Halen
> Collaboration: Beat It
> Year: 1982

“Beat It” was among the biggest hits ever for Michael Jackson, spending three weeks atop the Billboard Hot 100. For the song’s signature guitar solo, Jackson’s producer Quincy Jones contacted rocker Eddie Van Halen. The Van Halen guitarist thought he was being pranked, but when he found out the request was genuine, he performed the solo for free.

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19. Nelly and Tim McGraw
> Collaboration: Over and Over
> Year: 2004

Before LL Cool J and Brad Paisley collaborated, rapper Nelly and country musician Tim McGraw worked together on the song “Over and Over” in 2004. The song peaked at No. 3 on the Billboard Hot 100. In 2013, Nelly would also collaborate with country duo Florida Georgia Line on a remix of their song “Cruise.”

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20. Paul McCartney and Michael Jackson
> Collaboration: Say Say Say
> Year: 1983

One of the more famous of Michael Jackson’s collaborations was with Paul McCartney for “Say Say Say.” The pop dream team had worked on the song “The Girl is Mine” on Jackson’s blockbuster album “Thriller.” On “Say Say Say,” Jackson wrote most of the lyrics, and McCartney played several instruments. The single shot to No. 1 on the Billboard Hot 100 in December 1983 and stayed there for six weeks.

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21. Santana and Rob Thomas
> Collaboration: Smooth
> Year: 1999

Soulful guitar master Carlos Santana joined with Matchbox Twenty frontman Rob Thomas to produce “Smooth,” a single that was No. 1 on the Billboard Hot 100 for 12 weeks. Thomas wrote the lyrics, referencing songs written by Elton John and Ben E. King. “Smooth” was Santana’s first No. 1 single.

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22. Snoop Dogg and Willie Nelson
> Collaboration: My Medicine
> Year: 2008

Forty-seven-year-old rapper Snoop Dogg and 86-year-old country legend Willie Nelson may not seem likely to jive when it comes to music but there is one thing both performers enjoy immensely — marijuana. Perhaps inspired by the drug, the two worked together on Snoop’s country-tinged song “My Medicine.”

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23. Sting and Shaggy
> Collaboration: 44/876
> Year: 2018

English rocker Sting, who dabbled in reggae when he fronted The Police in the 1970s and 1980s, joined Jamaican fusion performer Shaggy on the collaborative album “44/876” in 2018. During an interview before the 2018 Grammy Awards, Sting said the “entire album was based on fun and rapport.” It was not one of Sting’s greatest successes; the album peaked at No. 40 in May 2018 on the Billboard 200, though it did win the Grammy Award for Best Reggae Album in 2018. 44/876 refers to the country calling codes for the United Kingdom and Jamaica.

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24. Taylor Swift and Zayn
> Collaboration: I Don’t Wanna Live Forever
> Year: 2017

Hit machine Taylor Swift collaborated with Zayn Malik for the single “I Don’t Wanna Live Forever.” The song, which was on the “Fifty Shades Darker” soundtrack, climbed to No. 2 on the Billboard Hot 100 in March 2017. Swift might be expected to more likely collaborate with her ex-flame Harry Styles, one of Malik’s mates in the boy band One Direction. However Swift is close friends with Malik’s girlfriend, model Gigi Hadid.

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25. Young Thug and Elton John
> Collaboration: High
> Year: 2018

Venerable English rocker Elton John liked the work of rapper Young Thug (aka Jeffery Lamar Williams), and producer Stelios Phili wanted to find a project that would involve both performers. He reviewed Elton’s discography, about 50 years of music, and found an a capella version of his 1972 hit “Rocket Man” online. That ended up on a tune what would become “High,” recorded in early 2016. Young Thug played a version of it for Elton when they met in London later that year. “High” was included on Young Thug’s “On The Rvn” EP that peaked at No. 17 on the Billboard 200 in October 2018.

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