Most artists will quake in their musical boots when meeting one of their heroes when those heroes are Mick Jagger, Keith Richards, Charlie Watts, and Ronnie Wood (aka The Rolling Stones) you’d be forgiven for putting those boots on the Richter scale. But then again, Amy Winehouse isn’t like most artists. We’re looking back at the moment Amy joined The Rolling Stones on stage to perform ‘Ain’t Too Proud to Beg’.

That stage was the illustrious main stage of the Isle of Wight festival. A mainstay of the festival circuit since 1969 it’s almost been around as long as the Rolling Stones. Almost. In 2007 the two icons of rock and roll met as The Rolling Stones took the ferry (more likely a helicopter) to the muddy fields of Newport to deliver an emphatic headlining performance.

As well as a host of their favourite tracks from their decades-long career, The Rolling Stones are also known to have a few aces up their sleeve by way of covers of iconic songs. This performance was no different as Jagger and co switched gears and into a rendition of The Temptations’ song ‘Ain’t Too Proud to Beg’. But while one ace was laid on the table another was soon to follow.

A few lines into the song Amy Winehouse arrives to a delayed but rapturous applause. Faced with the vocal challenge of matching Mick Jagger’s energetic performance, Winehouse shows off why, at the time, she was one of the most sought after and talented singers in the world.

[MORE] – A look back at the moment Keith Richards was nearly electrocuted to death on stage

2007 represented a time of success but tabloid turmoil for the singer. Winehouse had made her name with the Mark Ronson produced album Back to Black and the lead single of the LP ‘Rehab’ had shot Amy into the stratosphere of international success. But with fame and glory comes temptation and debauchery, something that would culminate in Amy’s maddeningly early death.

While Amy’s death now shrouds this performance with a touch of dark sadness, it is in this very act of performing that Amy felt most alive. It’s clear to see from the footage that she is just as excited to be in front of a massive crowd, performing with the biggest band on the planet, as she would be performing to 6 drunks in a working men’s club in Camden. To Amy, performing was everything.

She was damn good at it too. While other pop stars have tried to work with legendary rock stars and failed to match them in power (Rihanna with Bon Jovi, Taylor Swift with Jagger and Steven Tyler etc.), Amy takes the occasion in her stride and delivers a stunning performance. You can see how good it is by Mick Jagger’s admiring looks, watching Amy as a proud father might.

In truth, Jagger felt a deep connection with Amy. He was often quoted talking about her issues and one tabloid paper even suggested he wanted to officially become her father. While those ideas are best left to the red-tops, we think it’s best to sit back and watch both Jagger and Winehouse perform together in effortless synchronicity.

Watch as Amy Winehouse joins The Rolling Stones on the Isle of Wight Festival stage in 2007 to perform The Temptations’ ‘Ain’t Too Proud to Beg’

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