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26 Odd Pairings Of VMAs Past

One of the best things about the Video Music Awards is how famous people who are complete opposites will end up hanging out or collaborating on a skit at the awards. Here are 26 fantastic examples.

1. Coolio and Bjork

Mark Cardwell / Reuters

2. Shaq and Cindy Crawford

Fred Prouser / Reuters

3. David Letterman and Madonna

Mark Cardwell / Reuters

4. Dennis Rodman and Toni Braxton

Mike Segar / Reuters

5. Drew Barrymore and Courtney Love

Mike Segar / Reuters

6. Ricky Martin and Chris Rock

Peter Morgan / Reuters

7. Madonna and Lenny Kravitz

Sam Mircovich / Reuters

8. Mick Jagger and Bono

Ferran Paredes / Reuters

9. Tommy Lee and Christina Aguilera

Brad Rickerby / Reuters

10. Aerosmith and Kid Rock

Jeff Christensen / Reuters

11. Susan Sarandon and Lauryn Hill

Jeff Christensen / Reuters

12. N Sync with Marlon and Shawn Wayans

Jeff Christensen / Reuters

13. Madonna and Paul McCartney

Jeff Christensen / Reuters

14. Fatboy Slim, Spike Jonze, and Christopher Walken

Gary Hershorn / Reuters

Remember this?

15. Britney Spears and Christina Aguilera

Jeff Christensen / Getty Images

16. Gwen Stefani, Moby, and Eve

Gary Hershorn / Reuters

Remember this collaboration? Or this and this?

17. Michael Jackson and Joey Fatone

Gary Hershorn / Reuters

18. P. Diddy and Ben Stiller

Gary Hershorn / Reuters

19. Avril Lavigne and Lisa Marie Presley

Gary Hershorn / Reuters

20. Mark Wahlberg and DMX

Gary Hershorn / Reuters

21. Rudy Guliani and Jennifer Lopez

Gary Hershorn / Getty Images

22. David Spade and the Olsen twins

Win McNamee / Reuters

…We could still to Mary-Kate and Ashley as “the Olsen twins” in 2003, right?

23. Jimmy Fallon and James Brown

Gary Hershorn / Reuters

24. Naomi Campbell, Bruce Willis, and Diddy

Stringer USA / Reuters

25. Mandy Moore and Marilyn Manson

Stringer USA / Reuters

26. Eminem and a f*cking Crank Yanker

Win McNamee / Reuters

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