For many music fans, the Grammy Awards have been a questionable barometer of artistic worth. To wit: Christopher Cross claiming Best New Artist over The Pretenders, and DJ Jazzy Jeff & the Fresh Prince taking the first Best Rap Performance trophy over NWA and KRS-One. Although the award has had some dubious recipients in the past, it's nothing compared to the show itself. From hysterical antics to disastrous performances, the ceremony has never failed to entertain—intentionally or otherwise. Read on to revel in nine unbelievable moments in Grammy history.
Brand New Key
The Taylor Swift backlash officially began at the 2010 Grammys, when she sang a duet with Stevie Nicks. Despite claiming four awards that night, Swift was lambasted for her lack of range on "Rhiannon." The criticism may not have been fair: Swift wasn't the first to stumble during a live broadcast and she won't be the last. Her real mistake was being pitchy during the first Grammy broadcast that was tied in with Twitter and Facebook. Photo: AFP/Getty Images
Fade to Black
Singer Natalie Cole is no stranger to addiction (hence her memoir Angel on My Shoulder), nor to the Grammys (she's won nine in all). But, it still doesn't justify her critique of Amy Winehouse, who swept the Grammys in 2008. In response to Winehouse's big wins, Cole suggested that only teetotalers should claim awards. "I don't think bad behavior should be rewarded, so I was disappointed," Cole said at the event, adding, "There was some booing in the audience because a lot of people were very upset about it." OK, then! Photo: WireImage
What's Old Is New Again
In 2001, Shelby Lynne claimed the Best New Artist Grammy...for her sixth album. Granted, she wasn't up against the most daunting competition, but Lynne's win reinforced the perception that Grammy voters aren't all that familiar with the artists they honor. To her credit, Lynne referenced the ill-timing of the honor in her acceptance speech, noting that it had taken her "13 years and six albums to get here." Photo: WireImage
Take the Plunge
While it feels like Jennifer Lopez ascended to superstardom decades ago, it was only in 2000 that she really started to make headlines. In one of the best publicity stunts ever, the singer showed up to that year's Grammys wearing a Versace print dress with a neckline that plunged well past her belly button. Nobody remembers who won the awards that night, but everyone sure remembers J.Lo's dress. Pre-ceremony red carpets have never been the same. Photo: WireImage
Artist, Interrupted
The Wu-Tang Clan's Ol' Dirty Bastard wasn't pleased that his crew lost Best Rap Album in 1998 to Puff Daddy (Sean Combs's nom de plume at that time). So he picked the most natural time to air his grievances: right before Shawn Colvin's Song of the Year acceptance speech for "Sunny Came Home." Viewers weren't as appalled by the interruption as they were during the Taylor Swift/Kanye West kerfuffle at the MTV Video Music Awards in 2009, they were just really, really confused.
Fools Rush In
The 1998 Grammys shaped up to be a Bob Dylan fest, with the Academy set to honor the rocker-bard for Time Out of Mind, one of the greatest albums in his catalog. Amid the festivities that preceded Dylan's performance of "Love Sick," however, somebody forgot to secure the perimeter, allowing performance artist Michael Portnoy to boogie around the stage with "Soy Bomb" printed on his bare torso. But this wasn't even the greatest indignity Dylan endured that night. When announcing the Album of the Year nominees, Usher referred to him as "Bill" Dylan.
That's Life
After receiving a Grammy Living Legend award in 1994, Frank Sinatra took the stage to a deafening ovation. And then...well, he started talking. His witty—but rambling—monologue included thoughts about New York City and the lack of booze backstage, and a back-and-forth with the audience. And then mid-sentence he was gone, the victim of a producer's decision to cut away to a commercial. After the show, the Academy claimed the decision was prompted by Sinatra's people, who were worried that he'd gone too far off script. Photo: AFP/Getty Images
Lip Service
At the 1990 Grammys, Milli Vanilli put on quite the show, hopping around to and fro while "singing." As many listeners suspected, the group had been lip-synching on stage. But it turned out the duo was also faking it offstage, too—on disc and, well, pretty much any time a microphone was within arm's reach. When the ruse was revealed, Milli Vanilli became the first and only Grammy winner to have its award revoked.
Pedal to the Metal
It took until 1989—a full eight years after Mötley Crüe set a nation's toes a-tappin' with Too Fast for Love—for the Academy to honor hard-rock performers. Alas, the first time didn't prove a charm, with folk/progressive-rock mainstays Jethro Tull claiming the inaugural trophy for Crest of a Knave. It didn't help the Academy's credibility that the album cover prominently featured that most hard-rockin' of woodwinds—the flute—or that Jethro Tull triumphed over grittier rockers like Metallica and AC/DC. When Metallica won its first Grammy years later, drummer Lars Ulrich deadpanned: "We gotta thank Jethro Tull for not putting out an album this year." Photo: Redferns/Getty Images
