1) Michael Jackson on “Somebody’s Watching Me” by Rockwell (1984)
Hearing that song on the radio nowadays you would think to yourself, “That really really sounds like Michael Jackson, but why is he on this song?” Well, that song was the one hit by Rockwell. How does an unknown singer [affecting an English accent] get THE Michael Jackson to sing uncredited backup for him? Simple: just be the son of Motown CEO Berry Gordy. What, did you think they just met at a Dairy Quen and started hanging out?
2) Prince on “A Love Bazaar” by Sheila E (1985)
Wikipedia calls it a duet. Nah. It’s on her album, and although he wrote it, played on it and is singing the hook, it’s one of those occasions when a major artist is there to boost his protege.
3) Sting on “Money for Nothing” by Dire Straits (1985)
Sting provided both the signature falsetto introduction and the backing chorus of “I want my MTV,” as well as backing vocals throughout. For the “I want my MTV” melody, Sting borrowed from his own song “Dont Stand So Close to Me.”
4) Michael McDonald on “Peg” by Steely Dan (1977)
Two yacht rock powerhouses join forces on one iconic song, and the world is a better place because of it. Here’s an interesting fact: “Peg” was heavily sampled by De La Soul on “Eye Know” in 1989.
5) Chaka Khan on “Higher Love” by Steven Winwood (1986)
Not only did Chaka Khan absolutely rock it on this huge hit, she (and Nile Rodgers, btw) appeared in the MTV VMA-nominated music video as well.