1.
At the 2012 premiere of The Lorax — an animated movie for children, it should be stressed — the film’s star Zac Efron was on the red carpet when he reached into his pocket for something. But instead of just retrieving whatever he intended to grab, a condom slipped out onto the red carpet in full view of cameras. For a split second, time seemed to stop. Efron, realizing what had just happened, scooped up the condom, but the paparazzi had already snapped photos. The internet almost immediately exploded with jokes, memes, and endless speculation. Efron later addressed the cringe-inducing mishap, saying, “I never really had a pocket-checking policy before going on the red carpet, but now I think I’ll have to start!” You think, Zac?
2.
In early 2021, the hashtag #HereForCharli trended on Twitter, leading to TikTok sensation Charli D’Amelio writing in a since-deleted tweet: “I am looking through the ‘hereforcharli’ hashtag, and oh my goodness you are all so sweet to me. You have no idea how much your kind words warm my heart. I am so lucky to have you all by my side!! I love you bebs.” The only problem? The hashtag was not for D’Amelio but Charli XCX, whose friend and collaborator SOPHIE had just died from an accidental fall. Yikes. I bet you just shifted in your seat from secondhand embarrassment, huh?
3.
Rappers like to project an image as hard and badass, and 50 Cent is no different. Here’s one of his lyrics: “The drama really means nothin’ to me. / I’ll ride by and blow your brains out.” Damn, 50 Cent! Go easy! But in May 2014, the rapper looked softer than a kitten’s fur while throwing out the first pitch at a New York Mets game. His pitch didn’t just miss home plate — it soared wildly off course, veering nearly sideways toward a cameraperson. It wasn’t merely a bad pitch; it was possibly the worst pitch ever thrown, landing closer to first base than the catcher. The rapper later joked about how he would forever be immortalized in baseball blooper history, so he gets points for having a good attitude, but damn…embarrassing isn’t a strong enough word!
4.
In July 2010, Lindsay Lohan appeared in a Los Angeles court over alleged probation violations stemming from a previous DUI arrest. Embarrassing? Sure. But the cringiest moment came when photographers zoomed in on her hands and noticed she’d painted “Fuck U” on the nail of her middle finger. People roasted her online for this childish act of defiance, especially as she sobbed through the hearing. Lohan denied on Twitter that the swear was a message for the court, replying to a friend, “didn’t we do our nails as a joke with our friend dc? It had nothing to do w/court. it’s an airbrush design from a stencil xx.'” Um, OK. Thankfully, Lohan is in a much better place these days (she’s now a mom and has Freakier Friday on the way), but I bet she wishes she could take back the whole fingernail fiasco.
5.
During a 2016 presidential primary debate, Ted Cruz turned his moment in the spotlight into a horror show — thanks to a mysterious white particle. As Cruz spoke passionately, a small white chunk exited his mouth and clung to his upper lip. But that wasn’t the worst part — in a moment that will haunt me forever, Cruz casually licked it away. The internet exploded. What was that thing? A rogue piece of breath mint? A crumb? The most popular and disturbing theory? A tonsil stone — a little calcified deposit from the back of the throat that sometimes dislodges (google it at your own risk). Cruz never addressed the incident — because how do you even begin to explain that? — but it remains the most embarrassing thing he ever did…followed by the time he (I mean an intern, right Ted? Wink, wink) liked a porn video on Twitter.
6.
Throwing up in public is embarrassing for all of us, but doing it in front of thousands of fans? That is, well, thousands of times worse. In September 2012, during the opening night of his Believe Tour in Glendale, Arizona, Justin Bieber was performing “Out of Town Girl” when he abruptly turned away from the audience and vomited on stage. He briefly exited but soon returned to continue the show. What a trooper! But then, during “Beauty and a Beat,” he upchucked all over the stage again. Yiiiiikes. Bieber apologized to the crowd, claiming he was sick from drinking too much milk before the concert. To quote Anchorman: “Milk was a bad choice.”
7.
Winning an Oscar is supposed to be a glamorous moment — unless, of course, you wipe out on your way to accept it. That is what happened to Jennifer Lawrence at the 2013 Academy Awards when she tripped and fell to her knees while walking up the stairs to accept her Best Actress Oscar for Silver Linings Playbook. Upon (finally) reaching the podium, the crowd gave her a standing ovation, and she joked, “You guys are just standing because you feel bad that I fell, and that’s really embarrassing, but thank you.” Not gonna lie. It was “really embarrassing.” But the fall and her good-natured way of handling the awkward moment led to people applauding her as refreshingly “relatable.” Honestly, winning an Oscar can be more cringey/embarrassing, as you will see next…
8.
Winning an Oscar is supposed to help your career, not make people think badly of you. Unfortunately for Adrien Brody, that’s exactly what happened. When his name was called as the winner of this year’s Best Actor Oscar for his role in The Brutalist, Brody stood, pulled out his gum, and tossed it toward his partner, Georgina Chapman, before proceeding to the stage. (Seriously, bro? You couldn’t swallow it? Or put it in your pocket?) Then, upon reaching the podium, he embarked on an unfocused and un-extraordinary acceptance speech that would set a new record for its length — nearly six minutes. Even when the orchestra mercifully attempted to play him off, Brody persisted, requesting the music be stopped. He even remarked, “I’ve done this before. Thank you. It’s not my first rodeo.” (He previously won for The Pianist). Falling on the way to the stage doesn’t seem so bad now, does it?
9.
We can’t discuss embarrassing moments at the Academy Awards, though, without mentioning 2017…when Warren Beatty and Faye Dunaway mistakenly announced La La Land as Best Picture, only for it to be revealed the real winner was Moonlight. The confusion started when Beatty opened the envelope and hesitated, clearly sensing something was off. He looked to Dunaway, who, thinking he was being dramatic, read out La La Land. The La La Land team took the stage, gave emotional speeches, and celebrated what they thought was their win — only to be interrupted by Oscars staff frantically rushing the stage. As it turned out, the presenters had been given the wrong envelope — one that read “Emma Stone — La La Land,” which was actually for Best Actress. The La La Land team had to awkwardly stop their speeches as producers scrambled to correct the error. It still gives me cringe chills.
10.
Even more stomach-churning? The 2015 Miss Universe contest, where at the dramatic conclusion, host Steve Harvey declared Miss Colombia, Ariadna Gutiérrez, as the new Miss Universe. The crowd erupted in cheers, Gutiérrez beamed with excitement, and she was even crowned and handed flowers. But moments later, a visibly uncomfortable Harvey returned and awkwardly admitted, “I have to apologize. The first runner-up is Colombia… Miss Universe 2015 is actually Miss Philippines.” Gasps filled the room as pageant officials removed the crown from Miss Colombia’s head and placed it on Miss Philippines. Harvey later said, “I took my stupid ass back out there. I should have let them announce it the next day in the newspaper. I wouldn’t have caught none of the hell I caught.” Dude, it was your mistake, so admitting it was the right move. And what century are you living in where the newspaper would announce it the next morning?
11.
As you can see, live TV has a way of producing some of the most awkward and cringe-worthy moments, and one of the most infamous came on The Today Show in 2012 when Kathie Lee Gifford enthusiastically praised Martin Short’s decades-long marriage to his wife, Nancy Dolman. She gushed about their “beautiful” relationship and even asked how they managed to stay so in love after all those years. There was just one massive problem — Nancy Dolman had passed away two years earlier, in 2010, after a long battle with ovarian cancer. Short, ever the class act, didn’t correct her on-air. Instead, he graciously smiled and nodded along. Backstage, producers quickly realized the mistake. After the commercial break, a clearly embarrassed Gifford apologized and expressed her deepest sympathies to Short.
12.
Unless you’re from Australia, you probably don’t know who Molly Meldrum is. So why is he on this list? Because, well, just listen to this shit. In January 2023, Elton John was performing during his farewell tour when a visibly intoxicated Molly Meldrum (a legendary music TV personality in Australia) climbed onto the stage, hugged Elton, and then tried to join in the performance by pawing at Elton’s piano. That was awkward enough, but then things took an even wilder turn when his pants dropped, exposing his, uh, “down under.” Elton John continued playing, but reports suggest he wasn’t thrilled about the interruption — I’m sure the same could be said of everyone else in the arena. Meldrum later apologized, claiming his pants fell due to a faulty belt buckle, though few seemed convinced. What? Your genitals don’t immediately flop out when you don’t wear a belt? Sheesh.
13.
In maybe the most painfully awkward celebrity interaction of all time, pop star Kesha approached comedian Jerry Seinfeld on a red carpet in 2017 and enthusiastically asked, “Can I give you a hug?” Seinfeld, however, was not into the idea. With a polite but firm response, he quickly replied, “No thanks.” Kesha, still smiling, tried again. And again. “Please?” she pleaded. Looking increasingly uncomfortable, Seinfeld shut her down a third time with a simple “Yeah, no thanks.” The moment reached peak awkwardness when Kesha, clearly embarrassed, threw up her hands and walked off, while Seinfeld laughed uncomfortably and shrugged. Making this worse for Kesha is what Seinfeld later told an interviewer: “I don’t know who that was. I wish her the best.”
14.
In 2007, a video surfaced showing a drunk and shirtless David Hasselhoff struggling to eat a hamburger while lying on the floor. It turned out the Baywatch star’s daughter, Taylor-Ann, had made the video to show her dad the severity of his drinking problem. However, it was leaked to the public. While it was not a fun experience for The Hoff, he later said the video played a pivotal role in his recovery journey and acknowledged that the public exposure served as a wake-up call. As of 2025, reports indicate that Hasselhoff remains committed to his sobriety.
15.
Angelina Jolie is lucky she got her bizarro antics out of the way before the days of social media. In 2000, at the premiere of Gone in 60 Seconds, Jolie and her new husband, Billy Bob Thornton, could not keep their hands — or lips — off each other on the red carpet. They engaged in multiple full-on make-out sessions, and at one point, Jolie gushed: “We just had sex in the limo.” Ugh. Also in 2000, Jolie won the Best Supporting Actress Oscar for Girl, Interrupted, and declared during her acceptance speech: “I’m so in love with my brother right now.” That raised some eyebrows, but things got even weirder at the Vanity Fair afterparty where Jolie and her brother, James Haven, were photographed kissing on the lips. Damn. That’s a whole lot of uncomfortable behavior, Angie.
16.
In 2020, Madison Prewett, a contestant on The Bachelor, appeared to leave a fawning comment on one of her own Instagram posts, writing, “Beautiful date Madi. You are so genuine and real.” It seemed — oh, honey, noooo — she intended to post the compliment from a fake fan account but forgot to switch accounts. Fans on Reddit roasted her, saying, “Nothing says ‘genuine and real’ like having a fake instagram acct to comment compliments on your public one!!” and “Omfg commenting without switching to a fan account of yourself is embarrassing enough, but commenting that you’re so genuine and real is SENDING ME what a nightmare combination of cringe.” Prewett later claimed it was a friend’s comment mistakenly posted from her account. Sure, Jan. Sure.
17.
Sometimes people can mean well but still seriously embarrass themselves. Take Glee star Heather Morris, who, in June 2023, posted an interpretive dance tribute to George Floyd on social media. Yes, you read that right — an interpretive dance tribute to George Floyd (honestly, it sounds like something her Glee character Brittany Pierce would’ve done). In the video, Morris performed an emotional dance, set to spoken word audio addressing racial injustice. While intended as a heartfelt tribute, many viewers found the performance insensitive and self-indulgent, criticizing Morris for making the tragedy about herself. As one person wrote on Twitter: “this girl had not even 1 friend to tell her this was stupid. Heather Morris (Brittany) doing an interpretive dance to represent George Floyd’s death I really thought I’d seen it all.”
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