I'm wondering what songs coulda/shoulda been a good duet between any two artists.

I was listening to Pandora tonight, and GM's "Careless Whisper" was on, and followed by Madonna's "Take A Bow". It hit me that "Take A Bow" could have been a great duet between her and GM. It was also a time when GM was relatively out of sight for personal reasons. It might have served as a good medium to keep him in the U.S.'s market's view.

Have you ever had a similar idea when hearing a song and thought "Wow, _______ should have sang on this, too."?

Well, Michael Jackson had a few...

Bad (with Prince)
I Just Can't Stop Loving You (with Barbra Streisand)
In The Closet (with Madonna)

The only one that could have worked was ITC, but even that would have seemed a bit desperate on both their parts.

I read in the liner notes of her reissued self-titled album that Marvin Gaye told Donna Summer backstage at the 1983 Grammy Awards show that he wanted to collaborate with her. However he was killed before anything could proceed further. Another one she had in the works was with Bruce Springsteen on the song Protection. The two tried it initially as a duet but came to the agreement that since the song wasn't written that way, it would best work as a solo number.

Robert Palmer's "Addicted To Love" was originally recorded as a duet with Chaka Khan but WB and her manager scrapped it because they were about to release her "Destiny" album and didn't want her over-saturating the market. Also, Dennis Edwards "Don't Look Any Further" was intended as a duet with Chaka but she wasn't available so they went with the female on the demo, who was Siedah Garrett.

kitbradley said:

Robert Palmer's "Addicted To Love" was originally recorded as a duet with Chaka Khan

That would have been pretty great, actually.

Wasn't Prince the first choice for "Knew You Were Waiting For Me" with Aretha Franklin, then George Michael eventually took the gig?

namepeace said:

Wasn't Prince the first choice for "Knew You Were Waiting For Me" with Aretha Franklin, then George Michael eventually took the gig?

I doubt that. IKYWWFM was specially written as an opportunity for George to sing with Aretha.

I don't know if it would have been considered a duet, but Michael Jackson requested to work with Kraftwerk in the 1980s. He was turned down because they didn't want to give their sound away and they have refused other collabs. There was also a rumor that Mike & Boy George were going to do a duet.

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Although they have recorded duets together, Don't Look Any Further was first offered to Jermaine Jackson & Whitney Houston. They recorded it, but it never got released. Dennis Edwards & Siedah Garrett put it out. Another unreleased collab was We Be Ballin' which features Ice Cube, Shaq, & Michael Jackson.

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I don't know if there would have been any duets, but Morris Day was asked to produce Evelyn "Champagne" King.

Donny Osmond said in an interview that he & Michael Jackson were planning to do a duet around 2003 or 2004. Then Martin Bashir happened and Mike was not really in a mood to record anything. So that fell through.