Kanye and McCartney, mostly because of how old people responded to the "Look at 'Ye giving these up and coming artists a shot" tweets.

Metallica & Lou Reed/Lulu...

I made myself like this album simply because everyone else hates it...:banghead:

 

Junior Dad

In 1995 while taking a break from his British band James (The band that did the song "Laid"), lead singer Tim Booth hooked up with older dude film composer Angelo Badalamenti releasing a project entitled "Booth and the Bad Angel"

 

This was actually a decent collaboration spawning a handful of nice tracks, but IMO they were tunes that were consistent with, and could easily have been James tunes.

 

Here are two of those songs being performed in 1996 on Later with Jools Holland.

 

Though it's hard to distinguish his voice, the 2nd tune in this video actually shows Badalamenti singing backup while jamming on his keyboard.

 

Metallica & Lou Reed/Lulu...

I made myself like this album simply because everyone else hates it...:banghead:

 

Junior Dad

 

Whew it's a hard listen, but regardless it's still crazy interesting that they hooked up.

David Allan Coe and Pantera-Rebel Meets Rebel