Amy Winehouse
Credit: Peter Macdiarmid/Getty Images

One of the breakout moments of the 2008 Grammy telecast on CBS was a stellar live performance by Amy Winehouse. The dynamic singer, who passed away today at the age of 27, was a multiple nominee that night, so her appearance on the show was a must. Making it happen, however, was not as easy as it looked.

Flashback to 2008: Winehouse was undergoing treatment for drug addiction, which made it difficult for her to obtain a work visa to appear on the show, so CBS and the Grammy brass set up a contingency plan so she could perform live from a London soundstage. At the 11th hour, Winehouse secured that elusive visa, but it was too late for the show, so CBS stayed with Plan B. "We knew we could pull it off," said Jack Sussman, CBS' head of special programming. "Regardless of whether you are a rock star, a soul singer, a folk singer or a country artist, everybody wants to be part of the Grammys, so we knew she wanted to participate."

The performance occurred beyond the witching hour — it was after 3 a.m. when Winehouse appeared on the soundstage to perform. (Cuba Gooding Jr., who was in London at the time, was asked to introduce her appearance.) But it was a seamless transition from the telecast — which was broadcast live from the Staples Center in Los Angeles — to the U.K, where Winehouse performed "You Know I'm No Good" and "Rehab." By the end of the ceremony, Winehouse won five Grammys, including Best New Artist, Best Pop Vocal Album (for Back to Black), and Record of the Year, Song of the Year, and Best Pop Vocal Performance (all for "Rehab"). "Any time an artist gets that moment on a Grammy telecast, it is a moment for them to be celebrated by their peers and be seen by tens of millions in one moment in time," said Sussman, who can't remember the last time the Grammys went to such lengths to include a performance. "When you score big, you get on a roll and will forever be known as a Grammy winner. There is no doubt about the creative talent that woman had and what she exhibited in that moment in time."

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