18 Most Embarrassing Celebrity Moments Of All Time. Especially Number 3

Embarrassing Celebrity Moments

April 1st, 2017   |   Updated on February 28th, 2024

We’ve all had our share of embarrassing moments, but celebrities often have it worse. With the whole world watching their every move, they can find themselves in some pretty awkward situations. Here are some of the most embarrassing celebrity moments of all time that will make you cringe!

1. Justin Bieber Falling On Stage: In 2016, Justin Bieber was performing at a concert and attempted to jump from one side of the stage to another when he ended up slipping and falling flat on his face in front of thousands screaming fans! He quickly got back up like nothing happened though – what a pro!

2. Britney Spears Attacking Paparazzi: In 2007, an altercation between paparazzi and Britney Spears resulted in her attacking them with her umbrella outside her home – not exactly something she would want people to remember about her career…

3. Mariah Carey’s NYE Performance Fiasco: During Mariah Carey’s New Year’s Eve performance in Time Square 2017 things went terribly wrong as none of the sound equipment worked properly resulting is an extremely awkward moment for everyone involved – especially poor Mariah who tried desperately trying to get through it without too much embarrassment..

4. Kanye West Interrupting Taylor Swift At The VMAs: We can never forget this iconic moment when Kanye West interrupted Taylor Swift during her acceptance speech at 2009 MTV Video Music Awards claiming that Beyonce deserved better recognition than what she was receiving – talk about cringeworthy..

Being a celebrities and living in the limelight does come with its downsides. No matter where you are and what you’re doing, there’s usually someone nearby documenting your every move through the eye of a lens.

The awkward moments caught on camera came dangerously close to ruining their careers.

1. Fergie Pees Her Pants

Fergie Pees Her Pants: embarrassing celebrity photo

During a 2005 show, songstress Fergie could not ignore nature’s call. During her performance, a growing wet spot was clearly visible on the singer’s pants. Fergie admitted afterwards that she had peed herself. To cover it up, she quickly doused herself with champagne.

2. Kanye West Slams Head Into Metal Sign

Kanye West Slams Head Into Metal Sign

There is one good reason why walking away from the paparazzi with your head down is not a bright idea.The funny incident took place in 2013, a time when Kanye was trying to shelter his pregnant girlfriend from the blizzard of interest coming from the media.

3. Iggy Azalea Shows Too Much Skin

Iggy Azalea embarrassing cameltoe moment: Iggy Azalea Shows Too Much Skin

Iggy Azalea is not exactly a nun when it comes to showing her body. At the MTV EMA that showed a side vag was unintentional. The star desperately tried to hide her shameful parts with a dress that was designed to show.

4. Christina Aguilera Has Mysterious Liquid Flowing Down Her Legs

Christina Aguilera Has Mysterious Liquid Flowing Down Her Legs

Christina Aguilera has had her fair share of embarrassment throughout her career, but nothing compares to the rumors that irrupted once this photo was out. The incident took place in 2012, the year Aguilera released her last album, ‘Lotus,’ and gradually disappeared from the top of the charts. Could the two somehow be related?

5. Julianne Hough Paints Her Face Black

Julianne Hough Paints Her Face Black

The two times winner of ABC’s “Dancing with the Stars” thought there was nothing wrong in painting her face black to depict an African-American woman for Halloween. The result of her stunt was an incredible roast coming from all corners of the showbiz world and the most embarrassing moment of her career.

6. Katherine Heigl Suffers Embarrassing Wardrobe Malfunction

Katherine Heigl Wardrobe Malfunction: Katherine Heigl Suffers Embarrassing Wardrobe Malfunction

What can be worse than having to give an acceptance speech while holding a broken strap to cover your breast? winning the 2010 Female Star Of The Year at the ShoWest convention in Las Vegas also proved to be the most controversial moment of her career. Luckily for her, host Billy Bush was there to save the day.

He helped her stunning red dress stay in place, allowing Katherine to finish her speech and retain some dignity while walking down the stage. At least she did not create a Nipplegate like Janet Jackson in 2004.

7. Sofia Vergara’s Dress Rips Open

Sofia Vergara Wardrobe Malfunction: Sofia Vergara’s Dress Rips Open

We all hope to see Sofia Vergara wearing skimpy outfits, and on a few occasions, our prayers get an answer. Sofia’s 2012 Emmy wardrobe malfunction easily ranks as the most embarrassing. However, Vergara did not make a drama out of it and even shared revealing pictures on her Twitter account.

8. Britney Spears Shaves Her Head

Britney Spears Shaves Her Head

Ten years have passed, and the moment when Britney Spears shaved her head still haunts us. The embarrassing meltdown is even now unbelievable and appears a result of fiction. No one knows for sure what was going on inside Britney’s head when she threw away her beautiful curls.

9. Shave Us The Embarrassment

Shave Us The Embarrassment

If you’re going to strut down the red carpet at least make the effort to shave the pins! Precious star – Mo’Nique – opted for the au naturel look instead.

10. Katy Perry Nude-Suit

Katy Perry Nude-Suit

The 2012 MuchMusic Video Awards saw Katy Perry attempting to sport a naked body suit. In fairness, this had been attempted prior by Britney Spears and Jennifer Lopez. But come on Katy, you can do even better.

11. Pedo Bieber

Pedo Bieber

It’s only a matter of time before an angry parent files a pedophile charge against Bieber. What was he thinking in these photos?

12. Side Show

most embarrassing celebrity moments

LiLo knows how to put on a show – luckily her hair was covering her ample bust.

13. Nicki Minaj

Nicki Minaj nipple skip

The hugely popular pop singer had issues with her dress as she took to the stage in Vancouver… Yeah, I think we can tell what happened.

14. Gravity Is Evil


Perhaps Kathy Griffin had a bit too much that night. She seems to have forgotten how to use her legs.

15. Jennifer Lawrence Trips

Embarrassing Celebrity Moments-Celebs

You had one job and you failed. All she needed to do was walk up some steps!

16. Trousers Are Little Too Tight

embarrassing celebrity pics

When will Gaga learn? This time she decided to squeeze herself into a pair of leather trousers about two sizes too small.

17. Taylor’s Upskirt

Taylor’s Upskirt

We’re not sure how a sudden burst of wind can happen in an indoor stadium but the end result was a good shot of Taylor’s rear end. Now if only she wasn’t wearing her nude underwear.

18. Was Vanessa Anne Hudgens Planning On Returning The Jeans?

Celebrity Photos

Vanessa Anne Hudgens planning on returning the jeans.

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