Well Purple People Prince and Miles Davis to me and most of us collaborating is awesome, truth be told a lot of hardcore Miles fans I know really think a lot of his work during the 80's and early 90's not as great as classics like Birth Of The Cool or Bitches Brew. I think hardcore Miles fans look at it as a decline, me I think it was great, the birth of this cool union came about in late 1985 or early 1986 when Prince sent Miles Davis a tape with Can I Play With U?, and a note to go ahead and play what he wanted over it. According to the liner notes of The Last Words Tommy LiPuma chose Can I Play With U to appear on The Miles Davis Album Tutu, but by Prince's own omission he removed the track cause he felt like it didn't fit with the rest of the music on the album. Now I have listen to Tutu I think it would have fit well.
Something else I found interesting was the Marcus Miller track Full Nelson being referenced to the Miles track Half Nelson from the 50's "a bridge with the Prince track" and Prince's last name being Nelson. Prince and Miles also performed on New Years Eve at Paisley Park 1987, Miles also performed the Prince track Movie Star in the 80's often in concert, also if you notice in Under The Cherry Moon there is a copy of Miles Davis album You,re Under Arrest in the scene after the Girls and Boys performance. There was a Bootleg that surfaced called Crucial that was suppose to be Prince tracks with Miles playing trumpet, well that was debunked with the only track on the CD with Prince and Miles being Red Riding Hood AKA Can I Play With U? Claims also being maybe it was Altanta Bliss playing trumpet on the other songs.
In 1991 Prince did send Miles 8 instrumentals 3 which was played during his 1991 tour Jail Bait, A Girl And Her Puppy, and Penetration. I believe at one time I heard Warner Bros. actually courted Prince for Tracks he did with Miles for official release and Prince declined but the jury is still out on that. None the less if these 2 power house artists hooked up or had the chance to hook up this would have been Legendary.