Home CELEBRITY 25 Wildly Awkward Celebrity Moments That Truly Keep Me Up At Night

25 Wildly Awkward Celebrity Moments That Truly Keep Me Up At Night

25 Wildly Awkward Celebrity Moments That Truly Keep Me Up At Night

25 More Wildly Awkward Celeb Moments

1.

When Madonna got up on Jimmy Fallon’s desk and flashed the audience during his late-night show and Jimmy was NOT having it:

3.

And when he tried to give Taylor Swift’s Video of the Year VMA to drag queen Jade Jolie:

4.

When Kevin Jonas tried to give Jimmy Fallon a handshake/high-five, and Jimmy didn’t notice, so Kevin turned it into a clap:

5.

When Drake admitted his love for Rihanna in the most glowing speech of all time and then appeared to try to kiss her, and Rihanna was like, “…k” and dodged it:

6.

When Pink announced that she was gay, then immediately took it back while giving a speech at a Human Rights Campaign event:

7.

When Bella Hadid was asked about her “sneaker turn-offs” in an interview with Complex and became a huge meme:

8.

When James Corden and Patrick Stewart randomly got into it at the Glamour Awards in 2010:

9.

When Kendall Jenner messed up while introducing One Direction at the Billboard Music Awards:

10.

When Amy Schumer did a bit about Kirsten Dunst being a “seat filler” at the Oscars and it fell superrrr flat:

11.

When Jo Koy absolutely bombed at the Golden Globes and blamed his writers:

12.

When Jesy Nelson of Little Mix tried to do a Jamaican accent:

13.

When Emmys host Jimmy Kimmel laid down during Quinta Brunson’s Writing for a Comedy Series win for Abbott Elementary, and she almost tripped over him, then had to give her speech with him just lying there:

14.

When Jennifer Lopez went back to her old house in the Bronx and the person who lived there seemed unaware of who she was:

15.

When Kesha tried to hug Jerry Seinfeld on a 2017 red carpet, and he refused:

16.

When Britney Spears realized that Ryan Seacrest wasn’t gay:

17.

Speaking of Ryan Seacrest…when Seacrest tried to give Scott MacIntyre, the first blind person on American Idol, a high-five:

18.

Similarly, at the 2024 Oscars, when Laverne Cox stuck a microphone in Marlee Matlin’s face, even though she’s Deaf, and Matlin pushed the mic away:

19.

When Faye Dunaway incorrectly announced La La Land as the Best Picture winner at the 2017 Oscars (the winner was actually Moonlight), and the cast and crew took the stage and gave speeches before they realized the error:

20.

And when Steve Harvey announced the wrong winner in the Miss Universe pageant in 2015:

21.

When Ashlee Simpson was exposed for lip-synching on Saturday Night Live, and she did a little jig:

22.

When Flavor Flav confused Miley Cyrus for Gwen Stefani at the iHeartRadio Music Awards:

23.

At the 2015 Billboard Music Awards, when Guiliana Rancic kissed Kendall Jenner on the cheek, then went for the other cheek, but Jenner was already walking away:

24.

When Ben Affleck and Henry Cavill were asked about the terrible reviews for Batman v Superman: Dawn of Justice and Affleck fully dissociated:

25.

And finally, when Kim Cattrall scatted (I can’t even describe or screencap this moment — you just need to watch it yourself):

What’s an awk celeb moment you’ll never forget? Let us know in the comments!

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