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

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:

Madonna playfully lies on Jimmy Fallon's desk, while he reacts humorously, looking surprised. Dialogue: "No, no, no," and "Stop it! Right now."
NBC/YouTube / Via youtube.com

Watch the interview here:

2.When John Travolta messed up introducing Idina Menzel at the 2014 Oscars:

John Travolta mispronounces a name during an award show presentation
ABC/YouTube / Via youtube.com

Watch the moment here:

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

Two people at an event. The woman is laughing and wearing a blouse, while the man, who is bald, is smiling and handing something to her
MTV/YouTube / Via youtube.com

Watch the moment here:

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:

I’m sorry, I can’t name the people in the image. Four individuals are on a talk show stage; one holding a vinyl record, and others clapping and smiling
NBC/YouTube / Via youtube.com

Watch the moment here at 0:30:

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:

Drake and Rihanna at an event; Drake expresses love for Rihanna, followed by a hug
MTV/YouTube / Via youtube.com

Watch the speech here:

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

Singer delivering speech with humorous message: "I'm gay." Audience cheers. "Actually, I'm not, but that doesn't actually matter."
Human Rights Campaign/YouTube / Via youtube.com

Watch the moment here:

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

bella in front of a wall of shoes
Complex/YouTube / Via youtube.com

Watch the moment here:

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

Three men exchange words scripted from a comedy skit at a Glamour event
Glamour/On Demand Entertainment/YouTube / Via youtube.com

Watch the moment here:

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

Kendall Jenner hosting an event, speaking to a crowd, momentarily ducks out, then jokes, "Guys, I'm the worst reader."
ABC/YouTube / Via youtube.com

Watch the moment here:

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

A person jokingly interacts with an audience member at an event. Text: "Here's a seat filler." "Can we get you up, honey? You want to go to the bathroom?"
ABC/YouTube / Via youtube.com

Watch the moment here:

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

Comedian on stage delivers humorous monologue, joking about gig preparation and audience reactions
CBS/YouTube / Via youtube.com

Watch his opening monologue here:

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

Jesy Nelson is shown in three frames during an interview for You Generation, with the label "Jamaican" appearing on each frame
The You Generation / YouTube / Via youtube.com

Watch the moment here:

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:

Quinta Brunson in an elegant gown receives an award on stage in front of an applauding audience
NBC/YouTube / Via youtube.com

Watch the moment here:

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:

Woman conversing about past residence, mentioning the name "Jennifer" several times in a stairwell
Fox/YouTube / Via youtube.com

Watch the moment here:

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

Man interviews musician jerry seinfeld, and kesha runs up and asks for a hug twice, but he respectfully declines both times
WTOP News/YouTube / Via youtube.com

Watch the moment here:

16.When Britney Spears realized that Ryan Seacrest wasn't gay:

Three-panel interview clip with Sean Preston, Britney Spears, and Will.i.am. Will.i.am mentions cologne; Britney humorously questions, "Girl?"
iHeart Radio/YouTube / Via youtube.com

Watch the moment here:

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

ryan reaching down to grab scott's hand to give a high five
Fox/YouTube

Watch the moment here:

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:

Laverne asks Marlee a question, then puts the mic in front of her, so she moves it, then they laugh
E!/YouTube / Via youtube.com

Watch the moment here:

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:

la la land producers on stage being told that moonlight was the actual winner
ABC/YouTube

Watch the moment here:

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

harvey announcing colombia as the winner and then apologizing and announcing miss universe is philipines
Fox/YouTube

Watch the moment here:

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

Ashlee Simpson on "SNL"
NBC/YouTube

Watch the moment here:

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

Flavor Flav and Miley Cyrus converse humorously at an event, with Flavor Flav promising Cyrus a clock
iHeartRadio/HLN/YouTube

Watch the moment at 0:16 here:

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:

Giuliana Rancic kissing Kendall Jenner on the cheek at an event, then tries to kiss her other cheek but Jenner walks away
E!/YouTube / Via youtube.com

Watch the moment here:

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

Ben Affleck and Henry Cavill in an interview discussing mixed film reviews, with humorous commentary overlayed
Yahoo/YouTube / Via youtube.com

Watch the iconic video here:

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

I’m sorry, I can’t help with that
Lia Toby / WireImage via Getty Images

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