'90s Pop Star Moments That Make Us Cringe

The following article contains references to racism, sexism, and eating disorders 

The 1990s was a unique period for pop stars. With the internet in its primitive dial-up infancy, not to mention the absence of social media, many stars were able to avoid their every embarrassing foible being broadcast across the globe. Nowadays, Katy Perry may go viral for something as innocuous as an onstage eye glitch, but back in the '90s, singers could get away with all manner of faux pas without facing the scrutiny of the public. However, there were always eagle-eyed pop enthusiasts with the camcorder on hand to document celebs' awkward indiscretions for the history books.

As The Washington Post notes, it seems that '90s nostalgia is here to stay. Although these pervasive rose-colored memories like to paint the era as a simpler, more innocent time, the decade was — as Britney Spears would say — not that innocent. Truth be told, the '90s was chock full of the kinds of behaviors that would be seen as problematic today. As we uncover in this rundown, it was unfortunately pretty routine for pop stars to be subjected to body shaming, racism, and in one particular instance, the sexualization of a literal child. While we cringe at these offensive moments, the era was, of course, not without its calamitous, lighthearted blunders, with many of these cringeworthy moments rooted in slapstick or just plain awkward social debacles. So, let's shudder like it's 1999 and give the lowdown on '90s pop star moments that make us cringe.

Courtney Love gatecrashes Madonna's interview

Courtney Love has proven to be the queen of cringe over time. From inexplicably accusing former Nirvana drummer Dave Grohl of creeping on her daughter, leading to the then-teen begging Twitter to ban her mom from the platform to slamming Olivia Rodrigo for not DMing her about a London florist (yes, seriously), Love certainly knows how to roll an eyeball or two — or three. Subsequently, her antics generated more than a few headlines in the '90s.

At the 1995 VMAs, MTV mainstay Kurt Loder was interviewing Madonna when the singer was nearly hit in the head by an unidentified flying object; it was later revealed to be a makeup compact. A visibly inebriated Love was responsible. "Courtney Love is in dire need of attention right now," quipped Madge. Love then crashed the interview and rambled a slurred rant about no longer wanting to date rock stars. Although Madonna handled herself well and tried to keep things professional, Love was having none of it, proceeding to give impromptu impressions before embracing MTV reporter Tabitha Soren and apologizing for ever being mean to her. The whole debacle certainly gave off tipsy office Christmas party vibes.

Vice hailed the fiasco as the greatest VMA moment of all time, arguing that it typified a quintessentially '90s exchange that would never occur today.

Britney Spears' sexualized Rolling Stone cover

The Free Britney movement, which led to the end of Britney Spears' 13-year-long conservatorship, has shed light on the widespread ill-treatment of the beloved pop princess throughout her career. When Spears first emerged onto the music scene back in 1999, she was only 16 years old. But testament to the creepy obsession with underage girls in the '90s, Spears was heavily sexualized as a teen, famously wearing a skimpy school girl uniform in the music video for "...Baby One More Time." 

In 1999, the singer appeared on the cover of Rolling Stone for the first time. She was photographed sprawled across her bed in revealing lingerie, as she cuddled a Teletubby plushie. In the accompanying interview, Spears is constantly reduced to the sum of her parts. The article's male writer described her tanned thighs and large breasts in vivid detail. He also pointed out that she is 17 and ponders whether she can be classified as "bubblegum jailbait."

In a 2003 interview with GQ (via Britney Boards), Spears expressed immense discomfort with the photoshoot. "I didn't really know what the hell I was doing," she admitted. "And, to be totally honest with you, at the time I was 16, so I really didn't... [the photographer] was like, 'Undo your sweater a little bit more.' The whole thing was about me being into dolls, and in my naïve mind I was like, 'Here are my dolls!' and now I look back and I'm like, 'Oh my gosh, what the hell?'"

If you or someone you know may be the victim of child abuse, please contact the Childhelp National Child Abuse Hotline at 1-800-4-A-Child (1-800-422-4453) or contact their live chat services.

Diana Ross' epic fail

The United States is set to co-host the FIFA World Cup with Canada and Mexico in 2026, per NBC Sports. But the U.S. first hosted the tournament back in 1994, at a time when soccer was not as widely embraced among Americans as it has become. Bringing trademark pomp and pageantry to the opening ceremony, one has to admire the sheer effort put into the proceedings. In what was supposed to be an epic moment, Diana Ross was enlisted to score the first goal of the tournament. The former Supremes singer is, after all, a living legend, so if any pop superstar was going to score an awe-inspiring goal at the World Cup, why not Queen Diana? That is, if everything went according to plan — which, of course, it didn't.

Oprah, of all people, introduced Ross to the stadium, and what followed entailed Ross awkwardly miming to her 1980 hit "I'm Coming Out" as she danced across the field before her attempt at a penalty kick. To simulate the sheer power of her goal, the goalpost was supposed to split in half — except she wildly kicked the ball nowhere near the goal, which then fell apart anyway. This blooper with Ross turned the pageantry upside-down.

Interestingly, the actual tournament both began with a terrible penalty and ended with an even worse one, per FourFourTwo. Perhaps Ross' blunder foreshadowed Roberto Baggio's dramatic and shocking miss for Italy in the final, which resulted in Brazil triumphantly lifting the trophy.

The Spice Girls praise Margaret Thatcher

Musicians endorsing political candidates didn't start with Killer Mike and Bernie Sanders' bromance, or Beyoncé and Hillary's rallying feminist call to action. Back in 1996, the Spice Girls — then the reigning superstars of pop — endorsed conservative Prime Minister Margaret Thatcher.

At a time when there was widespread disenchantment with the Conservative Party, a growing number of popular stars endorsed Tony Blair's Labour Party as part of Cool Britannia in the lead-up to the 1997 election, per The Telegraph. So, it was especially shocking when the biggest pop group of the time backed the seemingly stale and austere Thatcher. The notorious Prime Minister had been credited with instigating mass unemployment and the privatization of public services; she was also dubbed "Thatcher, milk snatcher" for withdrawing free milk for school kids, per Slate. Yet, in an interview with The Spectator, Geri Halliwell hailed Thatcher as the original Spice Girl. "We Spice Girls are true Thatcherites," she declared. "Thatcher was the first Spice Girl, the pioneer of our ideology: Girl Power." Meanwhile, Victoria Beckham declared that the band would never vote Labour.

Melanie Chisholm, aka Mel C, has since expressed deep regret and embarrassment about the endorsement. Chisholm, who hails from the traditionally left-leaning and Thatcher-loathing Liverpool, told The Independent that she cringes at her bandmate's assertion that the former PM was a girl power pioneer, a claim that she passionately refutes. "They were never the thoughts or feelings that I shared... I don't think people think I'm a raging Tory!" she said.

Sandra Bernhard's racist Mariah Carey rant

As someone of mixed heritage, Mariah Carey has long been the target of racist abuse and skepticism regarding her ethnicity. For instance, in 1990, the Los Angeles Times called her "a white singer who has a black vocal style." This bizarre suspicion of the star's racial heritage was none more apparent than when comedian Sandra Bernhard lambasted Carey.

During a toe-curlingly offensive stand-up routine in 1998, Bernhard questioned the veracity of Carey's Black identity and chose to utter the N-word with it. Bernhard claimed that Carey was attempting to appeal to African-American audiences by befriending Black men, whom she described as "greasy," and referred to Black female singers as "fierce ghetto divas," per New York Magazine. Big yikes. The New York Times even casually referenced the bit during a review, never once castigating the comic for her use of racial slurs. Speaking with The Guardian in 2021, Bernhard said that she did not regret using the N-word in that moment.

In an interview with Mirabella (via The Mariah Network), Carey addressed Bernhard's words, lamenting the comedian's ignorance: "Sandra Bernhard used words that every African American I know — and definitely I, personally, find inappropriate... She implied I was a white person trying to be black. And it's offensive to me, because I've been a victim of racism on both sides."

If you or a loved one has experienced a hate crime, contact the VictimConnect Hotline by phone at 1-855-4-VICTIM or by chat for more information or assistance in locating services to help. If you or a loved one are in immediate danger, call 911.

An interviewer forces Victoria Beckham to weigh herself

With the body positive movement gaining immense traction and influence in the last few years, it seems unfathomable that it was once socially acceptable to force female celebs to prove their "worth" by weighing themselves on live TV. Sadly, that's exactly what happened with Victoria Beckham though.

In 1999, she appeared on "TFI Friday," hosted by Chris Evans  — no, not Captain America, but the British TV personality. At the time, Beckham had just given birth to her son Brooklyn. Evans began making inappropriate remarks about the singer's svelte postpartum body and asked her about her exercise regimen. "Is your weight back to normal? Can I check?" he asked Beckham, who begged him not to weigh her. Insistent, Evans brought out the scales and made Beckham weigh herself despite her pleas. When the scales exhibited a low weight, the audience and Evans applauded the star, intimating that thinness is intrinsic to a woman's value. 

In an interview with Vogue Australia, Beckham said that the incident was particularly painful due to the fact that her body has been constantly scrutinized throughout her career. "I'd just had Brooklyn and lost a lot of weight after," she recalled. "It happened to my mum after her pregnancies. It doesn't mean you have an eating disorder. And he made me stand on scales and be weighed. Can you imagine doing that nowadays?"

If you need help with an eating disorder, or know someone who is, help is available. Visit the National Eating Disorders Association website or contact NEDA's Live Helpline at 1-800-931-2237. You can also receive 24/7 Crisis Support via text (send NEDA to 741-741).

Boyzone's toe-curling dance

Irish band Boyzone was huge in the '90s — sort of like Ireland's answer to the Backstreet Boys. Although they were a colossal success, they would never quite live down the embarrassment of their first television appearance. In one of those "What were they thinking?" moments, the band appeared on Irish talk show "The Late Late Show" in 1993 and proceeded to dance in truly embarrassing fashion, all the while donning bizarre denim outfits and suspenders. To make matters worse, their dancing wasn't even synchronized, with Ronan Keating and the sadly departed Stephen Gately rocking out while their bandmates participated in a bad aerobics session. For some reason, Shane Lynch even decided to grab his crotch at the end of the performance.

The dance was such a mess that it continues to haunt the group to this day. Appearing on "The Late Late Show" decades later, the surviving band members were once again shown footage of the infamous performance. This enraged Lynch, who proceeded to curse and give the middle finger. Addressing his behavior on "The Niall Boylan Show" (via Her), he explained that he's sick of talk shows rehashing the clip, seemingly as a means of humiliating him and his bandmates. "They decide from the beginning to try to take us down a peg or two," he said. "The bottom line is I was just disappointed in the fact that we were very young, very innocent, and we had gone on to do amazing things, and what you want to do is chop us down."

Michael Jackson and Lisa Marie Presley's awkward kiss

Michael Jackson and Lisa Marie Presley were certainly one of the oddest romantic pairings of the '90s. The couple, who tied the knot in 1994, were subjected to various conspiracy theories; some claimed that Presley was encouraged to wed Jackson by the Church of Scientology as a recruitment ploy, per The Seattle Times.

In an effort to prove the detractors wrong, Jackson and Presley appeared hand-in-hand at the opening of the 1994 MTV VMAs. "Just think. Nobody thought this would last," Jackson told the crowd, gesturing towards Presley. He then initiated a kiss before leaving the stage with his lady love.

The kiss is particularly excruciating to watch considering that there have long been rumors that the Jackson/Presley relationship was nothing more than a PR stunt. According to Jackson's former maid Adrian McManus, the pair didn't even consummate their relationship. "From my recollection, she never stayed overnight in his private bedroom," she told The Sun. "Never once did I walk into Michael's bedroom and see them in bed or hanging out." In an interview with Oprah Winfrey, Presley admitted that she felt manipulated by Jackson and wasn't comfortable with the kiss. "He needed to do his thing," she said. "I would be there, uncomfortably, like the MTV thing... I did not want to do that, you know? It was just not in my nature to do that sort of thing."

Clive Anderson ignites the fury of the Bee Gees

The Bee Gees remain one of the most influential disco pop bands, renowned for their distinctive falsettos, tight pants, and bristly beards. Despite first rising to prominence in the 1970s, reaching the peak of their popularity thanks to "Saturday Night Fever," the band of brothers was still selling out arenas in the '90s. 

In 1997, the group was honored at the Brit Awards for their outstanding contribution to music. Also that year, they were interviewed by Clive Anderson for his talk show "Clive Anderson All Talk." Things got off to a poor start, with the host being pretty snarky toward the musicians, insulting them. When Anderson quipped that he forgot one of their songs existed, Barry Gibb shot back, "In fact, I might just leave ... You're the t***er, pal." Robin Gibb followed suit, with Anderson looking visibly stunned. Eventually, Maurice Gibb also decided to join his brothers in solidarity, leaving the host to conclude the show early, palpably flustered.

While the Bee Gees' exit was certainly cringeworthy, one can sympathize with the group's frustration at Anderson's characteristically snarky line of questioning. Reflecting on the fiasco in an interview with The Spectator, Anderson confessed that he regretted the way he conducted himself. "It was poor," he conceded. "But it was only meant as a joke ... But I forget that it's not always entertaining to everybody else. That's probably the mistake I was making with the Bee Gees."

New Kids On The Block's awkward farewell

New Kids On The Block typified the early '90s with their trademark boyband stylings and pretty boy ensemble. But by 1994, they found themselves very much out of favor. Their album "Face the Music" had bombed catastrophically, peaking at just No. 37 on the Billboard 100

That year, the group appeared on the British kids show "Live and Kicking," and one awkward interview ensued. The members appeared jaded and burnt out, giving half-hearted responses to host Andi Peters' questions as well as those from the throng of adoring tween fans who encircled them. The situation was exacerbated by the band's frequent inability to understand the questions that their fans, speaking in broad regional accents, put forth. At one point, Peters hinted at the end being nigh. "Because you've been so famous, if tomorrow you weren't, would you miss it?" he asked. "I wouldn't mind," replied Joey McIntyre. "I mean, it's fun being famous ... But I mean, I'm not gonna cry and, you know, break down about it."

Unsurprisingly, New Kids On The Block disbanded that year.. As Entertainment Weekly highlights, the group's demise signaled the end of an era, and this is none more apparent than in their woeful "Live and Kicking" interview. However, as cringeworthy as the interview may be, the group has since reunited and released new music.

That time Björk punched a journalist

Look, we've all had moments in which we regrettably didn't put forth our best selves, and it stands to reason that pop stars aren't immune to having bad days. But when said bad days lead to physical violence, it's difficult for even the most ardent stans to justify such behavior. Unfortunately, Icelandic pop superstar Björk had a very public confrontation with reporter Julie Kaufman in 1996 — one that would alter the image of the elfin chanteuse who once impishly referred to herself as a "grateful grapefruit."

The singer arrived in Thailand when Kaufman exclaimed, "Welcome to Bangkok," leading to Björk unleashing a ferocious attack. In archive footage, she can be seen pulling the reporter's hair and tackling her to the ground. As security pulled the singer away from Kaufman, she began to squirm free, perhaps in an attempt to go after Kaufman once more. Although she later apologized for the assault, Björk conceded that she attacked Kaufman, because she had reportedly been stalking her and her son for days, per Time. "My motherly instincts took over," the songstress said, per The Guardian.

Music producer Howard Bernstein, who produced two of Björk's albums, told The Telegraph that he was stunned by the outburst. "I was gobsmacked by that," he recalled. "It was like 'Whoah!' In front of her kid. It hit us all ... an attack's an attack." As noted in the book "Björk's Homogenic," the incident changed the public's perception of the Icelandic singing sensation.

Jarvis Cocker's moon...walk

Pulp launched to fame in the '90s with their idiosyncratic brand of indie pop that took a critical eye to British social life, notably via the hit song "Common People." Frontman Jarvis Cocker was known for his aversion to pretension and preening. Thus, when Michael Jackson landed in the U.K. to perform at the 1996 Brit Awards, Cocker decided to give the King of Pop a little moonwalk of his own.

Always a provocateur, Cocker disrupted Jackson's performance of "Earth Song" and proceeded to moon the audience; the Brits are nothing if not classy. In a bizarre and inexplicable move that's perhaps more cringey than the mooning itself, he also flapped his cardigan at the audience. Subsequently, he was escorted offstage and arrested for allegedly assaulting the children who were present, per Reuters. He was later cleared of all charges.

Appearing on "TFI" shortly after the incident, Cocker elucidated the rationale behind the debacle. "I was just sat there watching it and feeling a bit ill because he's there doing his Jesus act ... There was quite a lot of other people who found it quite distasteful as well," he said. So, the singer explained, he decided to rush the stage for the sake of the common people. "I may as well bend over and show me bum," he quipped in deadpan fashion. The incident had a lasting impact on Cocker's career, as he was dogged by false accusations of child assault for years, per The New York Times.