Fifteen years ago, the 50th Annual Grammy Awards ceremony at Los Angeles’s Staples Center (now the Crypto.com Arena) was an especially star-studded affair, even by Grammy standards — with performances by A-listers like Carrie Underwood, Aretha Franklin, Beyoncé with Tina Turner, Rihanna with the Time, Ye with Daft Punk, the Foo Fighters with Led Zeppelin’s John Paul Jones, and even a rock ‘n’ roll medley by Little Richard, Jerry Lee Lewis, and John Fogerty.
But the biggest star of the night, Amy Winehouse, wasn’t able to perform there in person.
In January 2008, a damning 19-minute video of Winehouse appearing to use drugs went viral after being obtained and circulated by U.K. tabloid The Sun; as a result of the fallout, the British torch singer entered rehab on Jan. 24, and was denied a work visa by U.S. officials when the Grammys were set to take place in February. “Unfortunately, her application for a visa to enter the United States of America has been rejected at this time by the American Embassy in London,” her camp’s statement read at the time. “Amy has been progressing well since entering a rehabilitation clinic two weeks ago and although disappointed with the decision, has accepted the ruling and will be concentrating on her recovery. Amy has been treated well and fairly by the embassy staff, and thanks every one for their support in trying to make this happen. There will of course be other opportunities and she very much looks forward to visiting America in the near future.”
Longtime Grammy Awards producer Ken Ehrlich — who “was never in favor of doing remote performances” and having “8,000 people in the audience, but nobody onstage” — reveals to Yahoo Entertainment that at first “there was some internal discussion” about whether or not Winehouse would be part of the 2008 ceremony at all, if she couldn’t make it to Los Angeles. “The vibe of a live event show like the Grammys is everybody’s supposed to be together in the room. So, it was a major conversation about whether we should break precedent — and break it for Amy,” Ehrlich, who produced the awards telecast from 1980 to 2020, recalls. “But come on — there was no way we were going do that show without her that year.”
Winehouse reportedly wanted to be part of the festivities, in some way: After all, she was the year’s top nominee, in six total categories, and was predicted to be the big winner. (She ended up winning five of those awards in absentia, including Record and Song of the Year for her eerie-in-retrospect signature hit, “Rehab,” and Best New Artist. At that time, she was the only fifth female solo artist to receive five Grammys in one night, following Lauryn Hill, Norah Jones, Alicia Keys, and Beyoncé.) And so, Ehrlich agreed to make a rare exception and go remote — just as long as Winehouse’s via-satellite performance felt like a special event.
However, Ehrlich and his team waited as long as possible to make this decision, hoping that Winehouse would somehow be allowed to travel to L.A. after all. “We stayed very optimistic about having her here, almost until the end; I don’t think it was much more than maybe a week or 10 days before that we finally found out she couldn’t,” he says. “And the very hot [Universal Records music executive] Monte Lipman, who was very much involved with her at the time, was instrumental. I mean, they were jumping through hoops.
“We always had good relations with the State Department, so we had been talking to them about trying to affect some sort of a waiver for her. But I think their philosophy was, ‘If we make an exception for her, then we open ourselves up for everything,’ and blah, blah, blah. You know, there were drugs involved, and there were other issues,” Ehrlich continues. “So, there was very little we could do. We relied on the State Department and we put all our eggs in their basket, hoping that they could help us and hoping that they were on our side. I think ultimately it proved that they kind of were on our side — but they had bigger fish to fry than a performance of a pop star on an awards show.”
Interestingly, the State Department did unexpectedly reverse its rejection of Winehouse’s visa, as reported by the New York Times just two days before the Grammy ceremony. But by that point, it was obviously way too late to change the plan that was now in place — which was to have Winehouse perform live, via satellite link, from London’s Riverside Studios, under the direction of Ehrlich’s colleague, veteran British director Hamish Hamilton. (Ehrlich recalls considering the legendary David Mallet, best known for directing music videos by Queen and David Bowie and major concert films by Pink Floyd and U2, for the job; however, Mallet was unavailable.) Hamilton’s directing résumé includes big-scale events like several Super Bowl halftime shows, Olympic ceremonies, the Emmys, the Oscars, but for Amy’s performance, he and Ehrlich decided to stay small.
“It was all about the uniqueness of this artist; it wasn’t about supporting her with big sound and lights. It was about putting her on an [intimate] stage. We agreed quite early on that we weren’t going to do any extraordinary things. Hamish came up with the idea of making it a table setting, so that it felt like a nightclub,” Ehrlich explains. “We weren’t trying to match the artifice of an awards-show look. And that was the plus of it: As it turned out, the performance was electric. It was really something.”
Given the fact that Winehouse’s Riverside Studios performance would take place at 3 a.m. London time — and that she had a bad reputation not only for the rampant drug use that had prevented her from attending the Grammys in the first place, but for frequently “missing shows and canceling things” — it would’ve been understandable if Ehrlich had been worried that this would be a live-televised disaster. And yet, he never demanded that Winehouse be sober for her performance — although it turned out that she actually was.
“I remember having a conversation with [Winehouse’s manager] Ray [Coberg], and Ray assuring me that she was going to be straight that night,” Ehrlich recalls. “It wasn’t part of the deal, of course. I didn’t ask her. She didn’t sign a paper agreeing to that. I never did. I don’t do that. If you talk to anybody about the way that I work, I believe most of them would say that I have this implicit faith in an artist’s ability to turn it on. So, no, I never asked for that [guarantee].
“The reality is, after all these years working with artists, there was no novelty about finding someone walking in stoned or whatever; that’s kind of part of the deal. But I do remember Ray making a point of it. I remembered him saying to me, ‘Don’t worry! She’s so excited and she’s really ready for this. She wants this to be great.’ I do remember that being volunteered by Ray. I’m sure it was not the first time he’d had to make that promise to someone.”
In unarchived Grammy-night footage in 2015’s Oscar-winning documentary Amy, Winehouse can be seen giddily watching as her idol, presenter Tony Bennett, announces her Record of the Year win on a video screen, then appearing utterly stunned as her bandmates and joyfully weeping mother Janis crowd around to embrace her. The day after the Grammys, one of the performers who was onstage that night, backing singer Ade Omotayo, spoke to British publication the NME about the “absolutely ecstatic” atmosphere at Riverside, and insisted that Winehouse was “a lot healthier” and “a lot happier” after her recent rehab stay. Omotayo even claimed that Winehouse refused to drink her celebrating crew’s Champagne that evening, instead going upstairs to quietly shoot pool. But there’s a heartbreaking Amy voiceover by the star’s childhood friend, Juliette Ashby, who was also at Riverside, recalling that Winehouse complained off-camera that the entire Grammy experience was “just so boring without drugs.”
Following her big Grammy night, Winehouse continued to struggle with addiction, and the media continued to bash her. In fact, rubbernecking reporters focused more on her Grammy acceptance speech’s off-the-cuff mention of “Blake, Incarcerated” — aka her troubled then-husband, Blake Fielder-Civil, who three months earlier had been arrested for his part in a pub assault — than on her triumphant near-sweep at the awards. Winehouse never released a studio follow-up to her Grammy-winning Back to Black album, and three and a half years after the 2008 Grammys, she was dead from alcohol poisoning, at age 27.
Ehrlich obviously didn’t get to spend time in person with Winehouse in 2008, although at one point he did consider “running over to London and having one eye-to-eye with her” before he realized he could not get away. (“We weren’t doing Zoom calls back in those days,” he quips.) But even though he was “detached because of the distance,” Winehouse made a major impression on him that historic Grammy year.
“She seemed fragile to me,” Ehrlich says softly. “The fact of the matter is, I love working with women artists. I just have always gravitated to them. … I’ve always had this soft spot for the vulnerability of female artists. … And I can specifically remember feeling a particular vulnerability that I was aware of with Amy. And it wasn’t just me that was aware of it; she was a mess, and people knew it. So, I was dealing with someone that was a strong personality, but someone that had a great deal of vulnerability about her.”
But Ehrlich sadly adds: “Over the years, very little surprises me about artists. I think one of the reasons that they are who they are is because they have a slightly tilted sense of life in general. The hoops that they have to jump through to get to where they are, and the disappointment and the depression and the rejection and all of that… I’m not surprised at pretty much anything I hear from an artist. It’s part of the kit that you get when you work with them.”