1. Conor Oberst & Fiona Apple
Imagine: the two melodramatic geniuses of the early aughts getting together. I’m not sure our hearts could take it but, like, holy cow what if they did a duet? Someone get on a “Criminal”/”Lover I Don’t Have to Love” mashup, stat!
2. Kanye West & Beyoncé
Ok, so they would probably be the worst couple of all time, but imagine the POWER. Music would hault, love would become synonymous with the apocalypse. This would be the end of everything.
3. Billy Corgan & Ashlee Simpson
Billy gets around a lot: he’s dated Tila Tequila, one of The Veronicas, and Ashlee’s sister Jessica Simpson. Why he opted for the blonde bombshell instead of the “La La” pop-punk princess is beyond me. Is it too late? I know you’d have to invent a time machine for this to happen but come onnnn.
4. New Kids On The Block’s Jonathan Knight & Ricky Martin
The greatest ’90s couple that never happened. Why didn’t this happen? Two of the most handsome men on planet Earth and they didn’t date. Boo.
5. Morrissey & Kim Deal from The Pixies and The Breeders
Morrissey probably shouldn’t date anyone, but if he did, it would have to be bassist Kim Deal. She’s talented, I’m sure they’re fans of each others music, it would just make sense. Deal’s happily married these days, though, and I’m pretty sure Morrissey is engaged to himself. So it goes.
6. M. Ward & Zooey Deschanel
The only thing that would make indie folk duo She & Him more adorable would be if they actually dated. Think about it!
7. Aaron Carter & Demi Lovato
Mostly because Carter said he has a thing for Demi. But also because how great would this be? Bringing together generations of Disney stars!
8. Mark McGrath & Shania Twain
They made a song together, it’s called “Party For Two” (it’s not very good) and I’m going to believe it was actually them professing their love for each other. The early ’00s were all about frosted tips and men’s shirts (not to mention, short skirts) and they’re to blame… so why didn’t they see that they were a match made in heaven?
9. Miguel & Mariah Carey
Because their new summer jam #Beautiful is the sexiest thing I’ve ever heard, imagine if that heat existed between them. Move over, Nick Cannon.