The teams of stylists, makeup artists and hairdressers used by our favorite stars usually ensure that they look fabulous when they hit the red carpet. Occasionally, though, something goes awry. Heidi Montag is currently holding it down for the year's worst street style, but tell us — who had the worst red carpet moment of 2008?

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Lyie Van Rycke
Herve Leger
Ashley Brooke
How the heck did I miss this Madonna pic this year!?! It looks like a bad Tinkerbell costume!
1Call me crazy or something, but I don't really think Gwyneth really deserves to be on this list... I can think of worst candidates.
2I voted Lucy! She is crazy, but I love that. Yeah Gwyneth looks cute.
3Madonna!!!
4well i thought that sharon's moment there was the worst.
5Gwyneth's dress isn't NEARLY as bad as that black lace and white satin combo Katie Holmes "designed" harem pants/jumpsuit she wore to her play premiere. That was seriously FUG.
From this list, the worst is definitely Madonna in my opinion.
6they all look equally stupid
7Um. Where is Solange Knowles on this list?
And I agree with Shannolyn that Katie Holmes' jumpsuit was AWFUL.
Out of these, I'd have to choose Madonna.
8Why are Sienna and Gwyneth on this list? There were worse people dressed this year!
I actually loved Sienna's outfit. Shame that boring people like Jennifer Garner always get praised, but Sienna, who takes fashion risks, get slammed.
9Gwen!!!!! Hated that dress. What was she thinking...it was ever so tacky.
10Definitely Gwyneth! The entire look was horrible.
11Madonna always looks like a train wreck to me. She looks exactly like Oscar the Grouch here. All the other ladies at least sometimes look nice.
12Um, old woman wearing the grassy knoll
13All these looks were horrible, but Madonna got my vote because that outfit was beyond tacky!
14I voted Madonna but Sharon Stone's was pretty bad too...
15Some of these were just one-time missteps (like Gwyneth), but Madonna ALWAYS looks horrible.
16wow, so much ugliness to choose from. I picked Madonna, but Gwyneth is a close second!
17hard, oh so hard..
18Definitely Madonna.Her dress is horific.
19Sharon and Rachels aren't that bad imo but the rest? Sorry, but if I can't vote for all of them but those two I can't vote for any of them.
Madonna does make me think of that Carol Burnett skit where she made a dress out of the curtans ala GWTW, accept with astroturf.
20MADONNA!!!! WHAT THE FFFF
21Where's the choice of "All of the Above" button? These "outfits" (for lack of a better term)are ALL truly HIDEOUS... But I guess Madonna's IS the WORST of the WORST.
Sugar - Please consider adding "All of the Above" and/or "None of the Above" buttons where appropriate. Thanks!
22Madonna-the dressed up Oscar the Grouch look really isn't working for her. Also, her legs are way too muscular to wear such a short dress. She looks disgusting.
23Yeah, I go for the "All of the above" option, too. Geez, do these girls not have real friends who tell them like it is?
24Madonna a la Oscar from Sesame Street.
25lol sorry, missangelique, you beat me to it.
26All Worst. but one vote for Madonna.
27I'm sorry but Madonna looks absolutely ridiculous...WTF?
28They're all pretty horrifying, but Madonna's the only one wearing an unmowed lawn for a dress.
29Madonna
30Madonna=train wreck
31Madonna definately worst, but Gwyneth close behind.
32These were all pretty bad. But I have to go with Gwyneth because she usually looks so great that this was a shock. The other women tend to look hideous more frequently.
33i think Sienna looks good.....Madonna on the other hand is far from looking good
34Madonna! She looks like a bird... a parrot maybe.
35Madonna. Rachel and Gwyneth's arent nice, but are definitely not the worst 5 of the year. Can't think of any names rightaway, but I'm fairly sure there're many others not featured as options here
36R-Bils needs to lose those bangs, they're like eating her face
37Out of these, Madonna. But what Katie Holmes wore for the premiere of All My Sons was horrendous!
38It's hard to choose they're all awful, but I'll say Madonna's is the worst.
39I don't like Sharon's dress but I think it looks good on her
madonna
40I'd have to say Madonna, she looks like she rolled around on the lawn and tied all the grass down its hysterical
41ya know there is unique but this is just ugly...lets wrap some fake grass on ya Madonna it will be the newest rage..
42Madonna looks like an sesame street monster in that outfit.
43What helwa1988 says is EXACTLY what I thought when I saw this awfulness. Ooh and loved the A-Rod jab, Sugar.
44Gwyneth always looks terrible.
45Oh and LMAO! @ pinkprincess1101 comment.
So true.
Hands down Madonna. What was she/her stylist thinking?
46Love Maddy, but this time she beat Bjork´s swan dress!
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