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Actually an interesting collaboration would be with Aretha Franklin and Bryan Ferry.
That aside, and I hate to be such a party-pooper, but why do I have to pick between The Rolling Stones vs. The Beatles or Frank Sinatra vs. Nat King Cole or Bob Dylan vs. Phil Ochs, Paul McCartney vs. John Lennon (or Brian Wilson), Janis Joplin vs. Tracy Nelson, etc., etc. Why can't I just enjoy the music that all these people have put out? Why is our culture so hung up about making a contest out of everything?

The Smiths v. The Cure
"Sheila take a bow" without a doubt!
And, take an encore, too.

It's too bad Carmen Miranda and Bob Dylan never collaborated that I know of.

I'd also like to see Dave Brubeck team up with Prince, John Tesh with Megadeth, Elvis with Jay-Z, The Vienna Boys Choir with Trent Reznor, etc. And for some reason, any musician outside of Broadway seems hilarious when coupled with Carmen Miranda. But maybe it's just me. Guns N' Roses with Carmen Miranda, Coldplay with Carmen Miranda, The Cranberries with Carmen Miranda (this might work if she had a cranberry hat), Rick James with Carmen Miranda, Lyle Lovett with Carmen Miranda, Barry White with Carmen Miranda, Pavement with Carmen Miranda, Arcade Fire with Carmen Miranda, etc. To bad she's dead, but with the miracle of COMPUTERS, I do think it's possible. The finest minds in science, engineering, film, and programming can hopefully come together for this important work.

Frank Sinatra vs Nat King Cole
Winner: Nat Cole !!!!!
Frank is over rated and i'm tired of people's obsession with him. he didn't write, he wasn't a musician whereas nat did both and was a greatly respected jazz pianist before he let out one of the most beautiful voices of our time.

Metallica vs. Slayer
Slayer wins! Enter to the realm of satan...
hair maintenance, speed, and thrills.

Bootsy Colllins vs James Brown

Eminem vs Moby

Brawn vs Brain

Jimmy Hendrix vs Miles Davis

Johnny Cash vs Elvis

Sarah Vaughan - Ella Fitzgerald

Sarah for they way she sang ballads

Both electroacoustic bands with cult followings. Xiu Xiu wins for simultaneously mastering pop songcraft and delivering gut wrenching ballads.

To the caller who chose Mariah over Whitney: You need to watch this video of Whitney singing One Moment in Time--then let's see what you think!

http://www.youtube.com/watch?v=8EbYmMb4lR4

Phoebe Snow and Patti Austin

Willie Nelson vs Johnny Cash

Probably Johnny since he influenced more (and, er, he's dead, thus passed on into legend), but both iconic

michael jackson vs. janet jackson

Billie Holiday vs. Ella Fitzgerald.

It's basically Feeling vs. Thinking (when I was younger it was Billie, now it's Ella)

Metallica vs Megadeth.
Metallica wins due to longevity.

what about hip-hop!? Jay-Z vs. Nas?

My lord, this show is embarrassing. It's like a JHS debate. Please, some of us listen to the music without the need for essays on conflict.

Brittney Vs. Christina?

Throwing a few out there for the sake of discussion:

Mogwai versus Explosions in the Sky - I vote Mogwai (more versitle)

Echo and the Bunnymen vs. The Psychedelic Furs - Tough one. Ian McCullough is utterly impossible for my American ear to listen to when speaking but enunciates so clearly when singing. The opposite is true for Richard Butler. However, Echo and the Bunnymen is still creating more music that is good and new sounding. And singing along is more important than monologues at concerts. So, Echo and the Bunnymen win! Yes!!! (Besides, Ian has better new wave arms - a very important factor for sure)

I agree with Michael A. from Manhattan! Where does John Schaefer come down on Steve Reich vs. Philip Glass?

And yes, let's go Red Sox!

Tricky vs. Bjork (?)

Zappa vs. John McLaughlin (?)

Justice vs. Crystal Castles (?)

SUPERGRASS vs. Blur
(Supergrass for me)

The Smiths vs. The Cure
(The Smiths any old day of the week).

Depeche Mode vs. New Order (?)

Megadeth vs. Metallica
(Megaaaaaaaaaaaadeth)

A couple of my favorites: Wagner vs. Brahms (Brahms). Ellington vs. Basie (Ellington)

A different kind of rivalry was Guns N' Roses v. Public Enemy, and thereby heavy metal v. hip hop, which was just embarrassing for everyone involved, but GNR more than anyone else.

Blur vs. Oasis

davide byrne vs paul simon - africa, brazil, etc

Motown vs. Stax?

Basie vs Ellington?

Paul McCartney vs John Lennon?

Notorious B.I.G. vs. Tupac Shakur.
Definitely Biggie. Tupac just can't match the wordplay and storytelling.

Steve Reich vs. Philip Glass. And I want to hear John's decision on that one.

brian wilson vs. paul mcartney
brian by a LOOOOOOONG shot....