The Academy Awards are the biggest night of the year for Hollywood, and finding the perfect dress can be tough... we understand. Most nominees have already hit up the Golden Globes, the SAG Awards, the BAFTAs, and so on... they may be experiencing couture gown fatigue by this point, yet there's no carpet more significant than the Oscars.
Every year, a few celebs make questionable choices when it comes to their dresses, but sometimes things are taken to a whole other level. In honor of this Sunday's Academy Awards, we're bringing back the wrost Oscar dresses of all time! Can you believe Sandra Bullock and Charlize Theron made this list?
Click after the jump to see why!
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Cher has got to be the all-time worst-dressed at the Oscars. So much so, in fact, that she makes our list three times for her dresses in 1988, 1989 and 1998. Her 1988 look (left) is one of the most memorable and talked about Academy Awards dresses of all time, since she looks like an ostrich that's into S&M. Cher didn't learn her lesson about showing too much skin in her sheer ensemble (middle) the next year, either. And her last look just shows why you shouldn't ask Spider-Man do design your red carpet look.
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It's hard to believe that the gal who looked like this at last year's Academy Awards could've ever done something so... wrong. However, the proof is in the picture. Angelina wore this boring gothic-inspired look to the show in 2000, when she won the award for Best Supporting Actress. The only problem: her win was for Girl, Interrupted rather than The Addams Family.
Yep... homegirl wore a swan to the Academy Awards. That's all. In this case, we're going with worst in the BEST way, because this is awful/awesome/we love you Bjork, don't change.
4. Celine Dion
Where in the world is Carmen Sandiego? Oh look, here she is, at the Oscars. One thing we can all take away from Celine's red carpet look at the 1999 Oscars is this: there is never an appropriate occasion for a backwards white satin tuxedo.
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Are we looking at Charlize's breasts, or are they looking at us? Besides the fact that Charlize's 2010 Oscar dress is extremely unflattering on her, those awkwardly placed floral designs lead into the dress's even more awkward train. This might not make the Worst of All Time list if worn on someone else, but we know gorgeous Charlize can do way better.
Runaway bride gone wrong? How many poodles had to be sacrificed for this one? Luckily, Sandra learned her lesson for future Academy Awards and we haven't been disappointed since.
Sometimes a little Oscars leg is a good thing (see: Angelina circa 2012). But Uma's 2004 ensemble is a like an ill-fitting wedding dress... with an out-of-place vest. It's confusing and just so, so bad.
If J.Lo was trying to make everyone at the 2012 ceremony fall into a trance with her rather hypnotic dress, we're not sure if she succeeded. But she definitely did not succeed in dressing well. As usual, Jennifer likes to bare ample cleavage, and that's fine. But those stripes scream "no!" and what happened to her sleeves? Were her arms just too big for the dress?
9. Sophia Loren
Oh, Sophia. The Italian legend was a sex goddess in her day, but by the 2009 Oscars, that day had come and gone, so maybe we didn't need quite so much cleavage. Of course, the real problem is that it looks like Sophia is headed to the junior prom... underwater... and got attacked by gold jellyfish on the way. A mustard-colored dress would've looked wrong on her in almost any cut, but this one is particularly horrifying.
Oops. Gwyneth bared her breasts playing her Oscar-winning role in Shakespeare in Love, so at the 2002 Oscars, she figured: why not flash 'em again? But not even Shakespeare could be in love with this look, from the oddly hippie no bra choice to the braided hair and overall dark, dour ensemble she's got going on here. This look is only appropriate for a The Craft 2 audition. We bind you Gwyneth, from doing harm...
So let's be real: who had the absolute worst dress in Oscar history?
Photos Courtesy of Getty Images