Top 50 Embarrassing Celebrities Photos All Time

Paris and Nicky Hilton 


Paris Hilton enjoyed her summer holiday a bit too much, as this picture shows. At least save it till you're under the water, eh Paris?

 




Cheryl Cole

 When she thinks you're not looking, Cheryl Cole is a secret bogey-picker! Who'd have thought it, eh?

Coleen Rooney

 It happens to the best of us... the riding-up-of-the-underpants catastrophe! Coleen Rooney gets stuck in, and operation de-wedgie is complete.

Fergie (Black Eyed Peas)

 Back in 2005, Black Eyed Peas singer Fergie famously relieved herself while on stage. Unfortunately, that wet patch on her crotch was a giveaway.

Robert Pattinson

 Even vampires get hot and sweaty sometimes. We still think Robert Pattinson is hot though, even with sweat patches.

Liv Tyler

 This kind of unladylike activity is best kept behind closed doors, Liv! It's not something you do in the middle of a busy street...

Justin Bieber

 Justin Bieber is the latest in a line of stars to take crotch-grabbing to new extremes. He looks pretty pained...

Miley Cyrus

 ...as does fellow teen star, Miley Cyrus.

Emma Watson

 Even Harry Potter starlet Emma Watson is getting in on the action. We're shocked!

Victoria Beckham

 Ah, the good old days, when Victoria Beckham didn't take herself so seriously and dressed like a pirate and pulled silly faces while attempting to sing.

Christina Aguilera

 Christina Aguilera clearly loves the taste of her lipstick.

Britney Spears

There are so many pictures of Britney Spears pulling faces (she's a pro) but this is one of the best! Something about the way her eyes are slightly crossed, and her chins are multiplied by three...

Kim Kardashian

 Yes, this is Kim Kardashian. No, she hasn't been possessed. We think.

Cameron Diaz and Tom Cruise

 Given that we know we'll never ever see a picture of Cameron Diaz looking bad in a bikini, or any form of fashion for that matter, we'll settle for this less-than-photogenic moment while nattering to Tom Cruise.

Charlotte Church

 And the prize for the biggest celebrity gob goes to... Charlotte Church

Lady Gaga


 Lady Gaga is pretty 'out there', so we're sure she doesn't really care that she looks like the lovechild of Rod Stewart and Liza Minnelli in this unfortunate picture.

Jennifer Aniston and Owen Wilson

 Jennifer Aniston barely puts a foot wrong, but sometimes her face does a funny and we have to laugh at it.

Olly Murs

 See, this picture would be embarrassing for most people, but X Factor hunk Olly Murs chose to take his kit off. He is clearly the man who cannot be mortified.

Rihanna

 e're not sure who should be more embarrassed in this picture: Rihanna, or the bodyguard who accidently grabbed her breast while guiding her through a throng of fans. Oops!

Bradley Cooper

 Bradley Cooper is sexy, period. But even he makes beauty errors - this time around it was his fake man tan on his face. Bradey... didn't anybody ever teach you how to blend?

Lindsay Lohan

 Someone should really teach young female celebs how to get in and out of cars gracefully...

Frankie Sandford

 ...no, seriously. Even though Frankie Sandford of The Saturdays has a perfect backside, it's still not the best angle, is it?!

Kate Moss and Florence Welch

 Kate Moss is one of the world's most beautiful and most photogenic women, but she still takes a corker of a picture sometimes. At least she can take solace in the fact that she will always be fabulous, no matter how many unruly paps are waiting at every unfortunate angle.

Amy Winehouse

 Who knew Amy Winehouse was this flexible? An attempt to cover up what looks like an embarrassing cleavage spill leaves Wino looking like she's frozen in an awkward yoga position. Tres uncomfortable, non?

Michelle Keegan

 Corrie star Michelle Keegan has a dig.

Kerry Katona

 Kerry! Weren't you ever told to eat with your mouth closed?

Cheryl Cole

 In the days before Cheryl Cole was uber-famous, she hadn't quite yet mastered the art of dealing with paparazzi flashes. Or styling.

David Arquette

 We wonder if David Arquette is ever going to look back at this picture in regret. We would. Purple and yellow velour do not a good outfit make.

Alex Reid

The gold one-piece will never be the same again. We're not sure why Alex Reid thought it was a good idea to dress up as his then-girlfriend Katie Price... and it still gives us chills just looking at it.

Michelle Heaton

Former Liberty X star Michelle Heaton hit a bum note with this bottom-cleavage showing dress.

Kate Winslet

Somehow we don't think this picture is hanging up in Kate's house. Thankfully, the Oscar-winning actress has now learned how to dress herself and protect her body parts from the glare of the paparazzi camera flashes.

Julia Roberts

Julia Roberts shocked the showbiz-loving world when she revealed her hairy armpit at the Notting Hill premiere back in 1999.

Boris Johnson

We know London mayor Boris Johnson is a man of many, many words - but perhaps he'd better consider not trying to talk and eat at the same time? Manners maketh the man, Boris.

Katie Price

Katie Price spends so much time and money on her appearance, she probably wouldn't want us looking at this particular picture. But we are. And we're laughing at her duck-face.

Keira Knightley

When Keira Knightley had a pixie crop, she also had a strange array of faces for the red carpet. This was just one of many. Eek.

Peter Andre

Let's take some time to reminisce and look back at pictures of celebs from years gone by... We know it was the 90s, but come on Peter! What were you thinking?

David Beckham

We actually think this picture of baby Beckham is rather cute, but still pretty funny too. Check out the hair!

Justin Timberlake

Oh dear... back in the day Justin Timberlake thought bleached hair was chic. And don't get us started on that fake ghetto stance. No, Justin, a big no.

Eva Longoria


Either Eva Longoria was really scared of the sun and whacked on a bit too much factor 50, or she had issues in make-up application.

George Clooney

George Clooney was, back in the 80s, the king of the mullets. It's weird to think he's an international heart throb when you take this picture into account...

Nicole Kidman

No. Seriously? This is Nicole Kidman?

Elizabeth Hurley

And don't even get us started on this picture! It is actually the elegant and glam Elizabeth Hurley, but from the 80s. She was a bit more alternative back then.

Matt Damon

Bourne actor Matt Damon ended up wearing this odd outfit back at school in the 80s. Please don't ask us what it is: we're just as confused about it as you are. As is he, apparently.

Janet Jackson and Justin Timberlake

Poor Trousersnake. We don't think we'll ever forget the moment back in 2004 when Janet Jackson had a wardrobe malfunction during Super Bowl half time. Neither will Justin Timberlake. In fact, the day shall forever be known as Nipplegate.

Kate Middleton

We guess Kate Middleton can be glad she took this tumble prior to her big day, otherwise it'd have been a right royal spill.

Lady Gaga

Well, really, did Lady Gaga expect not to trip wearing those impossible shoes? We love our heels as much as the next girl, but those are just crazy. They defy the laws of physics.

Sharon and Ozzy Osbourne

This picture isn't really embarrassing for Sharon and Ozzy, but we're sure it's mortifying for their kids! If they were our parents, we'd have locked them away by now. Parents shouldn't be cupping!

Sarah Jessica Parker

We're relieved to see that even slender celebs wear huge control pants.

Tom Cruise

We thought it was Top Gun that made him famous. Then, in 2005, Tom Cruise went and jumped on Oprah Winfrey's couch on live TV as a symbol of how much he loved Katie Holmes. And we can't look at him the same way ever again. Luckily couch jumping hasn't caught on as a national sport.

Davina McCall

Anyone other than Davina McCall would probably have a double chin or three to show off, so if you look at it from that perspective, it's not really that bad.

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