I think we can officially say that Willie Nelson has worked with absolutely everyone in his long career.
A while back I came across a blurb somewhere that mentioned that Willie Nelson had once recorded a song with Sinead O'Connor. You may remember Sinead as the bald Irish chick who pissed off Catholics by trash talking the Pope and ripping his picture up while performing on Saturday Night Live. She had that addictive song Nobody Compares 2 U back in the 90s.
Despite all her craziness, Sinead has a very interesting voice so after reading that she and Willie had once recorded a song together, I had to go find the proof. I ended up finding the official video for Don't Give Up, a song from Willie's 1993 "Across the Borderline" album.
Here's part of what it says about the song on Wikipedia:
"Don't Give Up" is a song written by Peter Gabriel and recorded as a duet with Kate Bush for Gabriel's album So. The single version was released as the second from the album in the UK in 1986 and fifth in the United States in 1987. It spent eleven weeks in the UK Top 75 chart in 1986, peaking at number nine. The verses, sung by Gabriel, describe a man's feelings of isolation and despair; the choruses, sung by Bush, offer words of hope and encouragement.
The song was included on Willie Nelson's Across the Borderline album, produced by Don Was, Paul Simon, and Roy Halee. Kate Bush's parts are sung by Sinéad O'Connor.
It was reported that funds raised by sales of the single were in excess of $300,000.