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Perhaps it wouldn’t have been so bad if it was just a run-of-the-mill performance. Lord knows Britney Spears has hashed up enough of those in recent years. But it was billed as her comeback. It was the moment she was to put her sticky divorce, her bald head, and that vomit-stained Gucci dress behind her. The MTV Video Music Awards were the erstwhile pop princess’s chance to show the world she could still sing, still dance, still dazzle.
Instead, on Monday night, she showed she was dead in the water. Having built a career on her looks and body, she waddled onstage in a too-tight, too-revealing outfit and revealed her former washboard abs had turned suburban.
But worse, far worse, she could no longer dance, pout, or, shock of shocks, mime. As the track played and she shuffled hopelessly around the stage, her flaccid mouth hung inert, forgetting to form words, missing cues, ruining her career.
Goodness knows who or what can save her now, but misery loves company and at least Spears has plenty of that. Today Janet Jackson had the grace to take the heat off Spears by reliving her “wardrobe malfunction” disaster for the hundredth time. The abysmal episode that saw Justin Timberlake reveal Jackson’s right breast during a Superbowl performance occurred three years ago, but the pair just can’t live it down. Today a US court will exhume the mess once more to decide whether the televised performance was indecent and broke broadcasting standards.
Of course, Spears, Timberlake and Jackson are not alone in their embarrassment. Music history is awash with cheek-warming onstage incidents. Remember the 1992 MTV Music Video Awards when Nirvana bassist Krist Novosolic tossed his guitar into the air only to watch it plummet directly into his face? What about when The Who’s Pete Townsend executed an energetic windmill manoeuvre and impaled his hand on his own guitar’s whammy bar? And then there was the time Metallica’s James Hetfield misinterpreted a stage cue and ended up standing in the middle of a pyrotechnic display, collecting a series of second and third degree burns for his error.
But no matter the scale of injury or degree of embarrassment, it is only Spears, Jackson and Timberlake’s contemporaries that can truly understand their pain. It is the musicians of today who know that at best their falls, fumbles and failures will be relayed around the world by guffawing bloggers and online reporters. Or worst, and most commonly, the incidents will be snapped by camera phones or filmed on pocket-sized video recorders and posted online to live on forever.
In the internet spirit of never, ever forgetting, we bring you the 10 most embarrassing onstage moments of the Noughties.
10 David Bowie
Had it been a bottle, or a can, or even a glow stick, it wouldn’t have been so embarrassing. But it was a lollipop that nearly took out David Bowie’s left eye during a Norwegian concert in 2004. A fan hurled the sweet on stage and seconds later Bowie was hunched over attempting to remove the calorific treat and accompanying stick from his eye. When he couldn’t, an aide sprinted on stage and proceeded to tackle the errant candy. He could have lost an eye. He could have been hospitalised. We get that, we do. But there’s just something dreadfully funny about a rock giant being brought to his knees by a lollipop.
9 Macy Gray
It couldn’t have happened in a worse place. The gravel-voiced singer was in her hometown of Canton, Ohio when she forgot the words to the American national anthem. Asked to sing the pride and joy of the country at a Pro Football Hall of Fame game, Gray strode on stage, opened her mouth and proceeded to deliver a wobbly, tentative version of the Star Spangled Banner. She went on to forget the words and was greeted by a stadium of hisses and boos. Mercifully a low-flying formation of aeroplanes eventually drowned out her abysmal attempts to save the number.
8 Mika
Britain’s favourite androgynous son put on a special performance in Tokyo last month when he excitedly leapt onto a bass drum during a rendition of Love Today, only to tumble right off, collecting his drummer on the way down and landing in a graceless heap of hair and heels.
7 Lily Allen
Adored even in foreign climes, all Lily Allen needed to do on a 2006 trip to Australia to promote her album was smile, sing and throw out the odd catty comment about Girls Aloud. Instead Allen agreed to be a guest DJ at an indie night gig. She attempted to mix one of her own songs and failed miserably, then proceeded to play R & B hits to a room full of indie fans. The crowd deserted the dancefloor in droves before booing the singer with such vigour that she was forced to squat behind the DJ decks to hide.
6 Beyonce
The epic tumble taken by the bootylicious Beyonce in Orlando, in July, deserves Guinness World Record status. Dressed in ravishing red and swinging her long locks about enticingly, the diva strutted towards a flight of steps only to trip and begin a remarkable tumble to the bottom. Starting with an arresting dive, the singer appeared to complete a forward roll and half pike before regaining her land legs and stumbling to her feet.
5 Ashley Simpson
Jessica Simpson’s little sister lived every lip syncer’s worst nightmare during an appearance on Saturday Night Live in 2004. The pouting yoof performed her single Pieces of Me without incident, but when she returned to the stage for her second number, things went awry. As the band bashed out the opening notes of a new song, the vocals of Pieces of Me floated into the audience. Simpson had her mouth still and her microphone at her waist. The vocals were swiftly turned off and she initially attempted to dance away the moment, until the full horror of the situation dawned and she fled the stage.
Perhaps the only thing more embarrassing was the explanation dreamt up by her manager father. She was only lip syncing because she had a nasty case of acid reflux which made her voice hoarse, he bumbled.
4 50 Cent
You almost expect it from a perky pop star like Ashley Simpson. But 50 Cent? Nobody picked the superstar rapper as a lip syncer. Of course, Mr Cent has never admitted that the reason he stopped performing mid-song at the BET awards this year was because a vocal track failed. No, 50 claims he was bumped by a dancer on a trapeze which caused him to lose concentration. He needed time to recover and so after singing a few lines, he stopped abruptly and walked into the audience spending the rest of the song shaking hands with fans. Ok 50. Whatever you say.
3 Britney Spears
What more can possibly be added to the post-mortem of Britney Spears' MTV awards performance aside from a quote from celebrity blogger Perez Hilton: "We are insulted, offended and disgusted by your “performance” at the VMAs.Are you f******* serious???"
2 Janet Jackson and Justin Timberlake
It was supposed to be a family show. After all, 140 million people watch American sports extravaganza The Super Bowl. But in 2004 when Justin Timberlake and Janet Jackson performed at halftime, he pulled away her costume to reveal her breast. Despite inquiries by the Federal Communications Commission, MTV, who produced the halftime show, CBS who broadcast it, and the ongoing court trials, the ridiculous reveal wasn’t the true embarrassment. No, that came later when the pair attempted to convince the public it had been an accident. Timberlake was only supposed to reveal Jackson’s bra, he claimed. Ah right. That will be why she was wearing a star-shaped nipple adornment then. But mostly it was the ludicrous way Timberlake tried to make the “accident” seem somehow official by labelling it a “wardrobe malfunction”. A wardrobe malfunction! Ba ha ha ha. The world will never stop laughing at that one.
1 Fergie
The horror! The cheek-warming, teeth-gritting horror! Black Eyed Peas singer Fergie, aka Stacey Ferguson, lived the ultimate nightmare when she wet her pants on stage in San Diego. Worse, a wily photographer caught the moment on camera. Red-faced, mortified Fergie was thus given a raft of nicknames, including The Urinator, The Whizzing Bandit and The Leaky Bladder and The Trouser Golden Showerer. (This list is by no means exhaustive.)
Earlier this month the singer told Heat magazine: "The most embarrassing moment of my life was when I had my 'accident' live on stage in San Diego. That's one picture I'll never live down.” We think she might be right.
Dishonourable mentions:
- Courtney Love throwing a microphone stand into the audience only to have it land on a fan's head and land her in court on reckless endangerment charges.
- Amy Winehouse leaving the stage to vomit after performing just one song. To the furious audience’s dismay, she never returned.
- Pete Doherty coming to blows with guitarist Patrick Walden during a Babyshamles gig at the Brixton Academy
- Destiny Child’s Michelle Williams tripping and falling to the floor during a bootylicious move.
- Robbie Williams takes a tumble while on stage in Leeds
- Razorlight giving weight to rumours of an iminent split by brawling on stage in Lyon.
- Ashanti’s fashionable but infinitely impractical netted, hole-strewn top slipping to reveal one of her breasts

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What about Paula Abdul about fifteen years ago at the VMAs? That truly was a sight!
Linda Brown, Helsinki, Finland
Growing up in a very image conscious world I think I may be more perceptive as to how women look. As a 22 year old woman I think Kate Moss looks a mess and dont think shes in shape, at the other end of the spectrum Britney is out of shape too. I would be horrified if I look like either of them. Britney does not look like how a woman should. Shes flabby. She's always going to be airbrushed and have loads of make up plastered on her. Ok shes had two kids - my mother had me and my bro at 25 and 27 respectively and still looked in better shape.
There is pressure on celebs to look good because they are idols to people, they are meant to look extra special and uber glam than the rest of us, hence adulation in the first place. They have the time, money to go to the gym, beauty treatments etc. If thats the line of work they are in - trading on their good looks then they should look good otherwise what's the point of them being singled out as special? The illusion is shattered for many fans
Helen, Derby,
I'm moving to the suburbs.
Rob, Toronto,
Has everyone forgotten Milli Vanilli? They were caught lip synching at the height of their careers in the mid 80s and it destroyed them. One of them committed suicide a few years later. They were synonymous with the concept of lip synching for years.
Dave C, London,
Its a disgrace that you criticise Britney for her appearance. Although her performance was terrible she looked absolutely fantastic; a refreshing change from these skinny waif types we see all too often oin the media and on television.
Gareth, Belfast, N. Ireland
to Toby in Calcutta, M Jackson had an embarassing moment when his hair caught on fire during a pepsi commercial. Though it was more of an accident.
Kiki, London,
There's been a lot of comment about Britney's figure. Or lack of. She looks like a girl should look. It is a sad message we are sending to young girls today that Britney's figure is somehow deficient.
As for the performance, she has generated the publicity required. A job well done.
Nic Corry, Hong Kong, China, SAR
Sam Fox & Mick Fleetwood presenting the Brits? Forget the year.
Michael Jackson appearing as a Christ like figure surrounded by children at Brits - was embarrassing without the knowledge we now have.
Jarvis Cocker mooning Michael Jackson at above Brits performance. (Embarrassing For Jacko)
Everyone who jetted in to appear at Live Earth.
Tony Brown, Newcastle,
The classic for me is still the attempt made by Mick Fleetwood and Samantha Fox to present a Brit Awards in the late 80s. The panic in their eyes as cues were missed and as they lost track of the autocue was truly wonderful. It was so bad that it came round a full circle to brilliance. I think they should have been retained to do the same every year. It would actually make the Brits worth watching.
Richard Williams, Twickenham, UK
Ahhhh Ahhhhh Ahhhhh. Thats the noise they make when I burn them.
Peter, Paul, Mary
Journalists who presumably aren't to be trusted with real news stories making money by bitching about pop stars - now that's embarrassing.
Dan Smith, Bath,
Anyone remember Rickey Lee Jones accepting her grammy, stumbling up on the stage so loaded on Heroin that she was hardly coherent. I believe that was in the late 70's when this type of thing was never seen on live TV.
LC, Columbia, SC
Has Michael Jackson - King of Pop, ever had an embarassing moment performing on stage? I think not.. though contributions welcome
Toby, Calcutta, India
Surely all of Pete Doherty's career is embarrassing.
David, Dublin, Ireland
Wasn't this decade but I'd say getting a band who's single was called "Jackey Wilson" to perform on the nation's biggest music show Top of The Pops in front of a giant sized photo of dart player Jockey Wilson, is the all time greatest most embarrassing pop moment; closely followed by having The Monkeys come on stage to play after a performance by the Jimi Hendrix Experience.
Justin Silver, London, United Kingdom
Kylie on stage in Germnay slipping badly on arse behind giant bouquet of flowers only to show no knickers on..hilarious.!!!
Another promo concert for her Body Language album had her lip syncing totally different words to what were being heard via backing track and another scene same place,",singing away live " but she was on floor with mouth closed.
M McGregor, Tunbridge Wells, UK
jap's eye pee?
Vinod, london, uk
I think when Beyonce fell down and bust her ass should have been the number 1 most embarrassing moment. How on earth was she left off the count down???
shy, yonkers, ny
geri... brit awards?!
Kidda, cityville,
Believe it or not there's nothing funny about almost losing an eye, particularly if, like Bowie, you already received permanent eye damage as a child.
Chris Jackson, London,
Sad that the Noughties has still produced nothing to compare with Sinead O'Connor (on the best PR advice money can buy) ripping up a picture of the Pope onstage, only to discover that she is a lot less popular than he is!
Desmond Persaud, Wimbledon, London, UK
What about when Larry Hagman forgot the words to the song he was performing at Queen Elizabeth's command performance.
Vic Marriott, Sarasota, U.S.A. Florida
You forgot one
Hint,
"Tito, Tito!"
mj, Neverland,
back eyed pees?
ringo, saskatoon, canada
Reading the US teenage stream of consciousness babble that passes for comment on YouTube is actually more embarrassing than poor Bouncy flipping all ends up down the stairs.
al loch, edinburgh, scotland