It's impossible to downplay the sheer amount of work put in when big acts go on tour. Scheduling, promoting, merchandise, security, rehearsing, lighting design, hauling & setting up massive amounts of equipment, and depending on the act creating elaborate set designs, costumes, hair & make up, and choreography, It's a huge production with many moving parts, and many things that can royally fuck up
Wardrobe Malfunctions
Sometimes something as simple as a wardrobe malfunction can become pretty infamous. But which Pop Queen wore it best...
Daphne & Celeste's "Fire the Manager" moment
Daphne & Celeste, remember them? That decidedly average looking female duo telling other girls they were U.G.L.Y, mainly due to a lack of alibi. They were confusing, and annoying, but thankfully short lived!
Someone had the bright idea of booking them to perform at the well respected Reading Festival.
In what has gone down as one of Reading Festival's most memorable moments, the irritating duo were quickly shown what the audience thought of their presence. Mainly by being continuously pelted by bottles of urine, meat, shoes, and even a wheelchair, until they surrendered & left... Limp Bizkit incite a riot
Everyone remembers Woodstock with a great affection - a free music festival positively brimming with peace & love. Woodstock '99 was supposed to celebrate the 30 year anniversary with similar vibes - this was not the case.
No lessons had been learnt from Woodstock '94 where they had pissed off the crowd, mainly by trying to stop them bringing in their own food & drink. Woodstock '94 had it's issues but still delivered some outstanding performances, including Nine Inch Nails mud wrestling before their set and performing an electric, mud soaked "Happiness in Slavery" which rightly won a Grammy for Best Metal Performance.
There were issues from the start with exorbitant ticket prices, a festival site built on hot tarmac in July's stifling heat, no adequate water supply, and opportunistic vendors overcharging for bottled water. It all led to an increasingly hostile crowd.
Add to that a massive number of fake tickets adding to the numbers, and an understaffed police presence, and things went from ugly to full stage riot & sadly rape. Limp Bizkit perhaps misjudged the mood of the crowd, but where urging crowds to "Break Stuff" in other gigs may have led to a hyped up mosh pit, in this instance the crowd obeyed, and started tearing the place apart. Jon Davis from Korn later said he wanted to "Punch Fred Durst in the fucking face" for his irresponsible part in inciting the riot.
Red Hot Chilli Peppers later took the stage, performing "Fire" in tribute to Jimi Hendrix. Again, the crowd took it literally...
Where the original Woodstock was all about peace & love, Woodstock '99 went down in infamy as the 2nd "day the music died".
The first being Rolling Stones' Atlamont Free Concert in December '69... Rolling Stones Free Concert - the day the music died
The Altamont Free Concert, in December 1969, was supposed to be the Woodstock of the West, but descended into extreme violence with multiple injuries, 3 accidental deaths, and the murder of Meredith Hunter.
If Woodstock was the dream, Altamont was the nightmare
The Rolling Stones '69 tour had sparked a lot of criticism due to high ticket prices, so they decided to end their tour with a free concert in San Francisco, with The Grateful Dead & Jefferson Airplane. It was a wonderful gesture, but poorly executed.
When the crowds arrived they found a desolate landscape with no trees or greenery (hardly the "West Woodstock" they'd been promised), precious little toilet & medical facilities, and a poor quality sound system. They quickly grew restless, with one concert goer greeting Mick Jagger off the helicopter with a swift punch to the jaw. With a restless crowd it was paramount that the bands were protected. Unfortunately the stage was only 1 metre off the ground, with no security fencing in front of it. The crowd could easily jump onto the stage, and they did. 
Understandably, nobody is keen to claim total responsibility for hiring Hells Angels as security. Some say they were only hired to protect the generators, others that they were only hired to assist and give people directions.
What actually happened is that they were paid with $500 worth of free beers (over $3k to adjust for inflation today) and stood guard at the front of the stage. There were multiple fist fights, all involving heavily drunken Hells Angels. During their set, Marty Balin of Jefferson Airplane was punched in the head, and knocked unconscious by a Hells Angel that was supposed to be protecting them, leading to The Grateful Dead refusing to perform, and leaving the venue altogether. 
Beating the crowd back with sawn off pool cues and biker chains
Meredith Hunter, an 18 year old black man, was stabbed & beaten to death by Hell's Angels as he brandished a gun & tried to get on stage with other fans.
You can see how uncomfortable The Rolling Stones were with the deteriorating situation, and Hells Angels presence, Jagger had stopped their set, asking the crowd to be cool, and urging Hells Angels to "stop beating up everyone in sight". 
The Altamont Free Concert is often cited as the concert that put the final nail into the coffin of the 60's summer of love momentum.
Fergie's unfortunate "accident"
And in lighter news, here's Fergie wetting herself on stage. Oh dear…
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