The 50 Most Memorable Red Carpet Fashion Moments

We look back at the good, the bad, and the ugly from past award shows to prepare for the Oscars this Sunday.

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Image via Complex Original
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The OscarsThe 50 Most Memorable Red Carpet Fashion Moments...

#50. Sacha Baron Cohen

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Year: 2009
Event: MTV Movie Awards

Complex Says:

We get it, you're trying to make a point about fur-wearing in the gay community, but can we save the leopard-print Underoo sets for cougar-in-training tykes instead of full-grown men?

#49. LeBron James with Kobe Bryant

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#48. Flavor Flav

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#47. Ice-T and Coco

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Year: 2005
Event: Body English Las Vegas party

Complex Says:

Since it wasn't Wet Wednesday or Thong Thursday, it's fair to guess that it must have been Fishnet Bodysuit Friday in Coco's world. And Ice-T went with a Dick Tracy look, probably because he's one of only a handful of heroes that comes complete with a penis joke.

#46. Christina Aguilera

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#45. Busta Rhymes

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Year: 1997
Event: MTV VMAs

Complex Says:

Just cause you're presenting with Martha Stewart, doesn't mean you need to bring your own table cloth dude. Can you believe this guy has his own fashion line?

#44. Tommy Lee and Pamela Anderson

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Year: 1999
Event: MTV VMAs

Complex Says:

Between Tommy Lee dressing like a flasher and the Easter bunny dying on Pamela Anderson's head, it kinda makes you long for naked sex tape moments. Clothes apparently aren't the answer for these two.

#43. Trey Parker and Matt Stone

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Year: 2000
Event: Academy Awards

Complex Says:

Approximately six-years later, the "South Park" creators admit that they were on acid after dressing in drag in homage to dresses previously worn by Gwyneth Paltrow and J. Lo. That doesn't excuse bulging metallic shorts though.

#42. Nicki Minaj

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Year: 2010
Event: American Music Awards

Complex Says:

This is exactly what would happen if Skeletor fell into a vat of acid and decided to enact his revenge by becoming an otherwise hot woman's outfit.

#41. T.I.

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#40. Robert Downey Jr.

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#39. Justin Timberlake and Britney Spears

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#38. Pharrell Williams

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#37. Perez Hilton

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#36. Nas and Kelis

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Year: 2008
Event: Grammy Awards

Complex Says:

There is a time and place to promote your album. It's not the Grammy's. Not to mention the fact that you're making all the racists super uncomfortable.

#35. Dennis Rodman

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Year: 2005
Event: Comedy Central Roast of Pamela Anderson

Complex Says:

It just seems redundant to make fun of Dennis Rodman's errors in fashion, but the Roast of Pamela Anderson is a classy event dude, pull it together!

#34. Michael Pitt

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#33. David Lee Roth

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Year: 1984
Event: MTV VMAs

Complex Says:

It's one thing when you go on vacation and you've already puked on all your shirts and still want to get leied at the luau, so you pick up a shirt at the gift shop... it's another one to don a Hawaiian-printed suit. I don't care if it was 1984 and you're David Lee Fucking Roth, there's no excuse.

#32. Tara Reid

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#31. Mark Ronson

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#30. Daniel Day Lewis

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Year: 2009
Event: "There Will Be Blood" premiere

Complex Says:

I guess one way of ensuring all of the milkshakes go to you is to convince everyone that you're nuts by dressing like a really dapper homeless dude all the time.

#29. Rose MGowan and Marilyn Manson

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Year: 1998
Event: MTV VMAs

Complex Says:

For the first time ever, no one gave a shit what Marilyn Manson was wearing because Rose McGowan's bead curtain-draped derriere was like an eclipse. Can't. Look. Away.

#28. Jon Hamm

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#27. Rihanna

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#26. M.I.A.

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#25. Madonna

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Year: 2009
Event: Met Ball

Complex Says:

Madonna looks a bit like a personification of the evil rabbit dude, Frank in "Donny Darko" but she's capable of causing way creepier nightmares with those sinewy arms of destruction.

#24. Mickey Rourke

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#23. Quentin Tarantino and Melanie Laurent

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Year: 2009
Event: Cannes film festival

Complex Says:

Tarantino generally does a good job of coming off like a bad-ass with his movies but then he did a tribute to the "Pulp Fiction" dance on the red carpet and it was like dad at your Bar Mitzvah all over again.

#22. Pete Wentz

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Year: 2006
Event: MTV VMAs

Complex Says:

Wentz rolled up to the red carpet with a literal monkey on his back. He was also wearing a cape, but no one noticed because he had a frickin Capuchin touching his face. It's like he didn't even watch "Outbreak"!

#21. Antonio Banderas

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Year: 2010
Event: Academy Awards

Complex Says:

Good ol' Greybeard is looking pretty good considering he's prolly not getting any booty tonight. Those hair dye for men commercials finally make sense!

#20. David Arquette

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Year: 2000
Event: 6th Annual Blockbuster Entertainment Awards

Complex Says:

Arquette never misses a chance to don a velvet suit and for this, he should be admired and feared. Just don't step on his blue suede shoes.

#19. Jared Leto

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#18. Jack White

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#17. Trey Songz

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Year: 2010
Event: MTV VMAs

Complex Says:

In homage to "Jurassic Park," Trey Songz sported a green, frill-necked Dilophosaurus jacket to the 2010 VMAs. Fortunately, no Newmans were harmed in this reenactment.

#16. Zoe Saldana

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Year: 2010
Event: Academy Awards

Complex Says:

Zoe proved that she's not above stepping on a few innocents to make it to the top and obviously, the victim here was Grimace. Unfortunately for everyone, Givenchy then made the poor guy into a flamenco gown.

#15. Carmelo Anthony

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#14. Russell Brand and Katy Perry

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#13. 50 Cent

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#12. Ray-J

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Year: 2010
Event: Soul Train Awards

Complex Says:

Despite starting at a high point in his career, Ray-J is still trying to prove he's a bad-ass and if that means wrestling a shark with his bare hands and having it made into a gunmetal sharkskin suit, he's gonna take it there.

#11. Bjork

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#10. Michael Jackson

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Year: 1984
Event: Grammy Awards

Complex Says:

Jackson gets a pass on any would-be fashion mistakes because man can dance and it's bad karma to speak ill of the dead, but he really brought it to the 1984 Grammy Awards. The bedazzled marching band suit and singular white glove were truly inspired and he totally deserved all eight awards he took home that night.

#9. Kanye West and Amber Rose

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#8. Christina Hendricks

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#7. Woody Harrelson

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#6. Brad Pitt and Angelina Jolie

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Year: 2009
Event: "Inglorious Basterds" LA premiere

Complex Says:

When all else fails, black on black and black leather on babe will usually win. If you happen to be two of the most attractive people in the world— double win. At least until that leather comes off and you realize it's like a greenhouse in there.

#5. Marques Houston

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#4. Lady Gaga

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#3. R. Kelly

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#2. Lil Kim

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#1. P. Diddy and Jennifer Lopez

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