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.”
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.
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.
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.”
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.