Most embarrassing celebrity pop culture moments

By Bryanne Salazar 8:28am PDT, Oct 18, 2019

Oct. 23, 2019, marks the cringe-worthy 15th anniversary of Ashlee Simpson's unfortunate performance on "Saturday Night Live." In a moment that will live on in pop culture infamy, Ashlee was on stage, ready to belt out another tune, when the music and lyrics to her song "Pieces of Me" started playing over the sound system before she was ready to perform — revealing that Ashlee had been lip-syncing. Mortified, she started to dance an awkward jig then walked off the stage. To commemorate the headline-making incident, Wonderwall.com is taking a look back at more of the most embarrassing pop culture moments we're sure celebrities would rather forget — but that we can't help but remember. Keep reading for more…

Not only do we remember when Tom Cruise and Katie Holmes were an item, but we distinctly remember how enthusiastic Tom was about their relationship early on. Of course, we're talking about his legendary May 23, 2005, couch-jumping incident on the set of "The Oprah Winfrey Show." During an interview with Oprah, Tom was clearly overjoyed about his new romance with Katie and at one point gave the talk show host double high-fives and exclaimed "I'm in love" before excitedly jumping up onto her couch like a child. Oprah's hilarious response? "He's gone. He's gone. The boy is gone." Tom and Katie would later have a child, get married and six years later go through a dramatic headline-making divorce, making his wild couch jump even more embarrassing.

RELATED: Hollywood's longest divorces

The Super Bowl XXXVIII Halftime Show starring Justin Timberlake and Janet Jackson on Feb. 1, 2004, delivered one of the biggest "oops" ever on live television when Justin yanked off a piece of Janet's clothing while they performed "Rock Your Body," exposing her bare and pierced breast to the entire stadium and a live TV audience of more than 140 million viewers. The shocking moment later dubbed "Nipplegate" sparked speculation for years — was it really an accident or was it staged?

The world will never forget when, on Sept. 13, 2009, Kanye West charged the stage at the MTV Video Music Awards, grabbed the mic from a shocked Taylor Swift, who'd just won the award for best female video of the year, beating out nominees Beyonce, Lady Gaga, Pink and more. The teenaged star had just barely kicked off her acceptance speech when Kanye interrupted — shocking everyone in the audience and viewers at home — saying, "Yo Taylor, I'm really happy for you, Imma let you finish, but Beyonce had one of the best videos of all time. One of the best videos of all time!" For her part, Beyonce looked completely mortified, which only solidified the bizarre outburst as one of the most embarrassing pop culture moments in history.

On July 30, 2012, Kristen Stewart went from being half of Hollywood's most idolized on- and off-screen couple along with "Twilight" co-star Robert Pattinson to one of Tinseltown's most scandalous stars when pictures of her kissing and caressing her married "Snow White and the Huntsman" director, Rupert Sanders, on July 17 were published. The backlash from fans was immediate and intense as Kristen was accused of ruining her three-year relationship with Rob. Although both Rupert and Kristen released public apologies for their bad behavior, it wasn't enough to save their relationships. Rob and Kristen broke up and got back together again but ultimately ended things for good in May 2013. Rupert's wife, model Liberty Ross — who played Kristen's character's mom in "Huntsman" — filed for divorce.

The pop music duo Milli Vanilli emerged in 1988 as one of the hottest new acts of the decade with songs like "Girl You Know It's True" and "Blame it On the Rain." By 1990, they'd earned a Grammy for best new artist — an award they would later have to return after the world learned that the duo, Rob Pilatus and Fab Morvan, never actually sang a word of their songs. In an embarrassing Nov. 20 press conference the same year they won their Grammy, Rob and Fab confessed that they were merely lip-syncing music recorded by three studio singers, exposing a ruse concocted by German record producer Frank Farian. Rob (left) and Fab became overnight outcasts and Rob struggled with depression and addiction. In 1998, Rob died by suicide at 32.

Long before randos were licking ice cream in grocery stores, pop star Ariana Grande was caught licking doughnuts and dissing an entire nation. In leaked security video from July 7, 2015, Ariana and then-boyfriend Ricky Alvarez were seen standing in front of a giant tray of baked goods inside Wolfee Donuts in Lake Elsinore, California. Both licked several desserts while laughing and Ariana could be heard saying, "What the f— is this? I hate Americans. I hate America. That is disgusting." The doughnuts were later unknowingly sold to customers (gross). Once the footage was made public, Ariana took to Twitter to apologize for her bad behavior, insisting she "loves America" and that her insults were about rising rates of childhood obesity in our country (um, okay?). She never explained why she actually licked the doughnuts.

No amount of damage control could erase this shocking moment that took place on April 12, 2015, when Drake appeared to be completely grossed out immediately after pop icon Madonna surprisingly made out with him while they performed at the Coachella music festival. After the picture went viral, Drake said it was "misinterpreted," adding, "I got to make out with the queen Madonna and I feel 100 about that forever." While we want to believe the rapper, the look of disgust on his face is hard to deny. One insider who's allegedly close with Drake said his reaction was due to Madonna's gross-tasting lipstick and not the actual kiss itself. Still, the picture remains an embarrassing and slightly hilarious moment in pop culture history that we'll never forget.

We're still ducking after the would-be fight between Cardi B and Nicki Minaj at the 2018 Harper's Bazaar Icons party in New York City. Reports claimed that Nicki might have stepped on and ripped Cardi's dress. Then the "I Like It" rapper was seen throwing her shoe at Nicki, though she missed. Reports also emerged about an alleged altercation between Cardi and a member of Nicki's entourage, but it was never confirmed. Videos of the drama soon emerged, with one showing Cardi removing her high heel while repeatedly screaming "f— yo' a– up!" (presumably at Nicki) and another showing Cardi throwing her shoe while screaming various epithets including "b—- come here!" as bodyguards protected Nicki. Cardi was later escorted out of the party and photographed with a giant lump over her eye. The feud continued on social media the following day and in the media. Cardi told W magazine that Nikki had been "taking a lot of shots at me" and had criticized her skills as a mother. Nicki declared on her "Queen Radio" show that she'd done nothing wrong. Though they eventually publicly called a truce, the incident itself paired with all the petty back and forth turned it into one of music's most embarrassing feuds that year.

This hilarious pop culture moment is brought to you by John Travolta at the 2014 Academy Awards. While introducing Broadway star Idina Menzel before her performance of the "Frozen" hit "Let it Go" at the Oscars, John royally screwed up her name, calling her Adele Dazeem. After the show, John was roasted for his mistake, but in 2015, Idina got her revenge. At that year's Academy Awards, Idina had the chance to introduce John: "Ladies and gentlemen, please welcome to the stage my very dear friend, Glom Gozingo," she said, giving the audience and viewers at home a good laugh.

Former Black Eyed Peas singer Fergie suffered a rare humiliation on stage in 2005 when she peed her pants while performing. It happened during the Peas' show at San Diego Street Scene that year when Fergie had a full bladder and was pumped full of adrenaline. She began jumping for the song "Let's Get it Started," causing the unfortunate accident, which was caught on camera by photographers. Fergie later talked about the moment, saying, "I wish it didn't happen … it was so embarrassing."

While Justin Bieber has endured his fair share of embarrassing public moments over the years, one of the earliest happened at the onset of his 2012 "Believe" tour, when a fresh-faced 18-year-old Justin puked not once but twice on stage in front of his fans. The reason? He claimed he "drank too much milk" before the show. After spraying the stage with stomach curds, Justin reportedly asked the audience if they still loved him, and they of course all screamed "yes!"

If you're going to interview Samuel L. Jackson, you should probably know who he is. In a cringe-worthy 2014 interview, TV reporter Sam Rubin accidentally mixed Samuel up with another African American film star, Laurence Fishburne, who'd recently starred in a Super Bowl commercial. When the reporter asked Samuel if he "got a lot of attention" for the football event ad, Samuel played dumb at first, asking, "What Super Bowl commercial?" before digging into the reporter, saying, "You're as crazy as the people on Twitter. I'm not Laurence Fishburne! We don't all look alike!" The reporter, clearly humiliated, apologized, saying, "My mistake … I'm guilty."

Thanks to Katy Perry, we'll never look at cake the same way again. At the 2008 MTV Latin America Awards, Katy performed her hit song "I Kissed A Girl" after jumping out of a giant multi-tiered cake, which she provocatively licked after singing the line "…and I liked it." At the song's end, Katy purposefully jumped onto the cake, covering her body in shiny pink frosting. All was going well until Katy attempted to walk away. The slippery frosting caused her to fall to the stage floor not once, not twice, but four embarrassing times in a row. Realizing she wouldn't get up without falling again, a humiliated Katy crawled off stage on all fours.

It's been two decades since the world learned that Matthew McConaughey was not only a hunk but a nudist. On Oct. 25, 1999, police were called to investigate a noise complaint at Matthew's Texas home and found a buck-naked Matthew dancing and playing the bongos at 2 in the morning. He was arrested for suspected marijuana possession — charges were later dropped — and spent the remainder of the night in jail before posting $1,000 bond. Years later, Matthew talked about the incident with Playboy, saying, "What's wrong with beating on your drums in your birthday suit? I have no regrets about the way I got there."

Falling is embarrassing, but falling in front of a packed room of Hollywood's biggest stars and a TV viewing audience of approximately 30 million people while receiving your first Oscar? That's downright humiliating. In 2013, Jennifer Lawrence had the unfortunate luck of being that person when she fell on the steps leading up to the stage to accept a best actress Oscar for her performance in "Silver Linings Playbook." The fall only lasted seconds, with J.Law quickly picking herself up and heading to the stage where she was met with a standing ovation. Making light of the accident, the actress said, "Thank you. You guys are just standing because you feel bad that I fell and that's really embarrassing." Hilariously, Jennifer actually stumbled again at the Academy Awards the next year, this time tripping over an orange cone after exiting her vehicle.

TV personality Kelly Osbourne suffered a case of foot-in-mouth-itis in 2015 that will live on in infamy. Her attempt to defend Latinos against then-presidential nominee Donald Trump seriously backfired when, on an episode of "The View," Kelly spoke out against Donald's hateful campaign rhetoric, saying, "If you kick every Latino out of this country, then who is going to be cleaning your toilet, Donald Trump?" It was meant to be a response to his claim that Mexico sent rapists and criminals to America. Instead, her insinuation that Latinos were only good for cleaning wealthy people's toilets caused an immediate backlash, with fans accusing the privileged daughter of rock icon Ozzie Osbourne of being clueless and a "liberal racist." Kelly later apologized on Facebook, saying, "I want to start by saying I ALWAYS take responsibility for my actions. In this particular case I will take responsibility for my poor choice of words but I will not apologize for being a racist as I am NOT." "The View" co-host Rosie Perez, who initially called Kelly out for her insensitive remarks, actually came to her defense, saying, "Kelly Osbourne is on our side, and I was sensitive. My disdain should only go to Donald Trump, so I'm sorry, darling."

Even the nicest guy in Hollywood needs to be bleeped! Oscar-winning actor Tom Hanks was a guest on "Good Morning America" in 2012 to promote his film "Cloud Atlas" and when pressed by the host to speak in the same futuristic accent as one of his characters in the movie, Tom accidentally dropped the f-bomb. The good-natured star immediately clasped his hand over his mouth and apologized profusely to viewers, saying, "Man oh man, I'm sorry, I slipped into a brand of acting… I have never done that before. I would apologize to the kids in America who are watching this right now… and the next time I'm on this show there will be a seven-second delay."

Want proof Beyonce is superhuman? During a 2013 concert in Montreal, Bey decided to get closer to her fans as she sang a heartfelt rendition of her hit song "Halo." The only problem? Beyonce sat right next to a powerful mechanical fan that quickly sucked up her hair, yanking her head backward. Any mere mortal would stop singing and cry out for help, but Beyonce didn't miss a single note. The Grammy-winning singer kept the show going as security and a concertgoer worked to untangle the mess, with only those closest to the stage realizing what had happened. A few concertgoers, however, caught the embarrassing moment on video, preserving Beyonce's legacy as one of the baddest women in the music biz.

Actor Shia LaBeouf has endured more embarrassing moments than most (remember his #IAMSORRY live art performance where he allowed fans to touch him?). But one that still remains the stuff of pop culture legend is his bizarre 2014 masked appearance at the Berlin Film Festival premiere of "Nymphomaniac Vol. 1." On the red carpet, Shia was photographed wearing a paper bag over his head with the words "I'm not famous anymore" written across it. While Shia never explained the move, it was widely believed to be a part of his months-long art-inspired apology tour after he was caught plagiarizing in his short film "Howard Cantour."

We can never unsee the graphic performance delivered by singers Robin Thicke and Miley Cyrus at the 2013 MTV VMAs. During a raunchy rendition of Miley's "We Can't Stop" mashed up with Robin's "Blurred Lines," the scantily clad former "Hannah Montana" star twerked against Robin's crotch and re-enacted scenes of personal pleasure with an oversized foam finger. Fans and critics were outraged and intrigued by the overtly sexual performance. Years later, Miley later revealed to The New York Times that it was Robin — who was left relatively unscathed by their controversial duet — who'd asked Miley to be "as naked as possible" for the song.

One of the most jaw-dropping, embarrassing mistakes ever made on live TV came courtesy of TV host and comedian Steve Harvey during the 2015 Miss Universe pageant when Steve — who was the host that night — wrongly announced Miss Colombia as the winner. After Miss Colombia was given her sash, flower bouquet and crown and began waving to the cheering audience, Steve awkwardly announced his error, saying, "I have to apologize. The first runner-up is Colombia… Miss Universe 2015 is Philippines!" As expected, both beauty queens seemed equally stunned, with neither knowing what to do following the revelation. Steve attempted to regain control of the situation, telling the crowd, "It was my mistake. I take responsibility," but people continued to boo him. Following her rescinded win, Miss Colombia bravely appeared on Steve's daytime talk show where he tearfully told her, "You're the one person I really wanted to talk to. Because of the mistake I made, I cast you into a spotlight… a place that I never intended to, that I would not want to happen to anyone. I just want to say how sorry I am."

Remember when pop music stars Nick Lachey and Jessica Simpson were not only married but had their own reality TV show? On a 2003 episode of "Newlyweds: Nick and Jessica," the blonde "I Wanna Love You Forever" singer made hilarious pop culture history when she famously asked her hubby while sharing a meal on their couch, "Is this chicken what I have or is this fish? I know it's tuna but it says 'Chicken by the Sea.'" Nick seemed shocked by Jessica's naive question and looked away from her several times before saying, "You act like you've never had tuna before," then told her it was tuna and 'Chicken of the Sea' was merely the brand name.

What could be worse than falling off the wagon in front of your daughter? For former "Baywatch" star David Hasselhoff, it was having the world witness his relapse. In a leaked 2007 video, a seemingly drunk David — wearing only jeans — is seen lying on what appears to be a bathroom floor, sloppily eating a cheeseburger. In the video, David's then-16-year-old daughter Taylor can be heard reprimanding her father, telling him not to get any more alcohol, saying, "… if there's any alcohol in your system you're gonna be fired from the show." According to a statement later released by David, the video was never meant to be seen by anyone else, but "got into the hands of individuals who are not worthy of mentioning, who maliciously released the tape for their own self purpose." David went on to claim he was a recovering alcohol who suffered a "brief relapse" and had learned from the embarrassing experience.

Rap artist 50 Cent might be a baller whose lyrical game is strong, but his embarrassing ceremonial first pitch at a May 27, 2014, Mets vs. Pirates game left a lot to be desired. The "Candy Shop" rapper made everyone take cover when, instead of tossing the baseball to the Mets' catcher, he accidentally hurled it to the left, missing his mark by a long shot. The good news is that Fiddy wasn't the first celebrity to throw a bad opening pitch (Snoop Dogg and Bruce Willis come to mind) but his was definitely one of the funniest.