The 25 most surprising winners in Grammy history

The most notorious Grammy win in the show’s history, producer Frank Farian’s studio concoction Milli Vanilli wound up winning the award for Best New Artist. In many ways, the win made sense: the duo were a phenomenon, reigning over the pop charts with such hits as “Baby Don’t Forget My Number,” “Blame it On the Rain” and “Girl I’m Gonna Miss You.” The problem is Farian was relying on his Boney M blueprint: he hired professionals to sing the material in the studio, then found pretty frontmen to mime the words. Once the deception was revealed, the scandal tarnished the Grammys, forcing NARAS to revoke their win.

Steely Dan had been away for 20 years when they released their Two Against Nature album in 2000. That was big news for fans, many of whom were older and not inclined to pay attention to Eminem, Radiohead and Beck, who were the duo’s main competitors at the 2001 ceremony. Many observers expected either Eminem or Radiohead to win the award, but Steely Dan was precisely the kind of act the Grammys love: veterans who relish the immaculate sound of a high-end studio. In retrospect, their win seems obvious.

At the height of grunge mania, the Best Rock Song Grammy went to a track that was old enough to legally drink, performed with all the coziness of a cardigan. Eric Clapton’s Unplugged arrangement of “Layla” isn’t without merit: it’s a clever rearrangement, flipping the original’s unbridled passion into a sweet shuffle. That said, the win seems distinctly un-rock and roll, especially when considering Nirvana’s “Smells Like Teen Spirit” and Pearl Jam’s “Jeremy” were two of its chief competitors.

Macklemore & Ryan Lewis were all the rage in 2012 and 2013, when the Seattle hip-hop act unexpectedly catapulted to the top of the charts all around the world with “Thrift Shop.” That smash hit, along with “Can’t Hold Us” and “Same Love,” helped the accompanying album The Heist break through to the average Grammy voters, which meant that The Heist beat Kanye West’s Yeezus and Kendrick Lamar’s Good Kid, M.A.A.D. City for best rap album. Plenty of rap fans were upset. Macklemore was one of them: he notoriously posted an apologetic text to Kendrick Lamar after taking home the Grammy.

Make no mistake: Tenacious D rock hardcore. The duo of Jack Black and Kyle Gass are true believers in the power of metal, yet their 2015 win for a cover of Dio’s “The Last In Line”—issued as part of a tribute album to Ronnie James Dio—feels like an inadvertent slight to such fellow nominees as Slipknot and Mastodon, or perhaps an indication that the Grammys don’t take metal especially seriously.

After over a decade’s worth of steady, worthy work, Shelby Lynne finally had a critical and commercial breakthrough in 1999 with the splendid, soul-inflected I Am Shelby Lynne. The Grammys took the album’s introductory title to heart: they treated it as a debut album, even though it was her sixth record. On artistic merits, Lynne deserved the award—it was just hard to call her a “new” artist in 2001.

Arcade Fire became an indie-rock sensation in 2004, earning a following so big that the band had spilled into the mainstream by the start of the next decade. Despite their acclaim and audience, their nomination for The Suburbs for Album of the Year in 2011 seemed like an award enough. Instead, they bested Lady Gaga, Eminem, Katy Perry, and Lady Antebellum, a true upset in Grammy history.

By 1981, it was clear that Christopher Cross was a success. His eponymous debut reached the Top Ten, as did the singles “Ride Like the Wind” and “Sailing.” Nevertheless, his sweep of all the major Grammy categories in 1981—he took home Album of the Year, Record of the Year, Song of the Year and Best New Artist—was a shock, setting up expectations for a career that he couldn’t quite sustain.

It could not be said that 1978 was the hippest year for Best New Artist at the Grammys, not when the coolest act nominated was either Andy Gibb or Shaun Cassidy. That said, both Gibb and Cassidy were teen idols, something winner Debby Boone decidedly was not. Boone had the year’s runaway hit with the inspirational “You Light Up My Life,” so her win couldn’t be called unexpected, but it did make the Grammys especially square that year.

Usually, the surprise in the Best New Artist category lies in the industry awarding a business-friendly act with a clearly limited shelf life. That wasn’t the case in 2012. That’s the year that indie giant Bon Iver wound up getting the trophy, proving NARAS was actually paying attention to what was hip—if not quite paying attention to the details. Justin Vernon’s Bon Iver was granted the Best New Artist award a full five years after the 2007 release of his debut album, For Emma, Forever Ago.

Everybody assumed Beyonce would win the grand prize of Album of the Year in 2017 for Lemonade. Not only was the album widely embraced as a masterpiece, it followed Beyonce’s equally well-regarded eponymous 2013 album, which lost in the same category in 2015. Everybody assumed wrong: Adele’s 25 won the crown in 2017, to the surprise of many, including Adele herself, who said during her acceptance speech that she didn’t deserve the award.

The times were changing in 1979. Punk was starting to transform the face of modern rock and the Grammys acknowledged the shift by nominating both the Cars and Elvis Costello, two of the more tuneful practitioners of New Wave. These artists weren’t nearly as commercial as Toto, a collective of studio superstars who would soon dominate the pop charts in the early 1980s, both on their own and as Michael Jackson’s support on Thriller. But none of these acts won Best New Artist, though. Instead, the honor went to A Taste of Honey, who made the splendidly silly “Boogie Oogie Oogie” disco hit and little else. They’d fallen off the charts by the time Michael Jackson’s Thriller came out.

At the height of Beatlemania, the Fab Four did not take home the trophy for Best Rock & Roll Recording. That honor went to Petula Clark, an English singer who wasn’t exactly part of the British Invasion, nor was she particularly rock and roll. Bobby Vinton’s “Mr. Lonely,” another track that was more pop than rock, was also nominated. The other nominees in the category? The Beatles’ “A Hard Day’s Night,” Roy Orbison’s “Oh, Pretty Woman,” and the Righteous Brothers’ “You’ve Lost That Lovin’ Feeling”—all songs that would go on to become rock and roll classics.

Jazz usually tends to fly under the mainstream radar; it’s for the fans, not a general audience. That may be the reason why Herbie Hancock’s win in 2008 for his Joni Mitchell tribute album River: The Joni Letters seemed like a surprise: all the chatter was about Amy Winehouse’s Back To Black and Kanye West’s Graduation, two albums firmly within the zeitgeist. But River: The Joni Letters was outside of time and fashion, making it just the kind of timeless record that is appealing to Grammy voters.

The short-lived Best Contemporary R&R Performance—it lasted three years in the middle of the 1960s, as the Grammys were trying to figure out what to do with rock-inspired music (hence the R&R tag, one that was applied to various vocal performances of the time)—was an embarrassment of riches in 1967. The category featured “Eleanor Rigby” by the Beatles, “Monday, Monday,” by the Mamas and the Papas, “Last Train to Clarksville” by The Monkees, and “Good Vibrations” by The Beach Boys. The winner deliberately didn’t attempt to ride this mod vibe: it was “Winchester Cathedral,” a novelty hit by the New Vaudeville Band, who specialized in sprucing up the sounds of the roaring ’20s.

A large part of Marc Cohn’s appeal in 1991, when his debut single “Walking In Memphis” rocketed toward the top of the pop and adult contemporary charts, is that he didn’t seem fashionable. His earnest, low-key piano ballads seemed like a throwback to the golden age of the singer/songwriter—precisely the kind of catnip Grammy voters couldn’t resist. He may also have been helped by the fact that all his fellow Best New Artist nominees were R&B musicians, including Boyz II Men and Seal, so they effectively split the vote that year.

Bill Danoff and Taffy Nivert, the married couple at the heart of Starland Vocal Band, established their music biz credentials by co-writing “Take Me Home, Country Roads” before starting the act that became Starland Vocal Band. In 1976, the pair had a hit with “Afternoon Delight,” a cheerful celebration of a lazy afternoon fling that captured everything tacky about the 1970s. “Afternoon Delight” was such a ’70s sensation that the group wound up besting Boston and The Brothers Johnson for Best New Artist in 1977, then promptly faded away.

When Paula Cole won Best New Artist in 1998, it wasn’t that she was unknown. Indeed, with “Where Have All the Cowboys Gone?” and “I Don’t Want to Wait,” she had two hits bigger than any single from fellow contender Fiona Apple, either in the 1990s or beyond. Apple, however, was a critical darling, as was fellow nominee Erykah Badu, while Hanson and Puff Daddy were commercial juggernauts, so Cole’s win seemed to come out of nowhere in 1998.

By most measures Lionel Richie’s Can’t Slow Down is an unimpeachable choice for Album of the Year. It’s a massive hit by a figure beloved by the industry, the kind of musician who made giant hits with ease. The problem is, Can’t Slow Down came out the year of Prince’s Purple Rain, Bruce Springsteen’s Born In The U.S.A., Cyndi Lauper’s She’s So Unusual, and Tina Turner’s Private Dancer—albums that defined an era and are still considered classics. Comparatively, Can’t Slow Down is an artifact: a bright entertainment tied to its time.

British troubadours who expertly approximated the sunkissed soft-rock of the United States’ West Coast, America wound up beating not one but two homegrown practitioners of their chosen style, the Eagles and Loggins & Messina, for Best New Artist in 1973.

Robert Goulet would become an entertainer so beloved he’d winningly cameo in Tim Burton’s Beetlejuice, but when he took home the Grammy for Best New Artist in 1963, his recording career was off to an inauspicious start. The star of Broadway’s Camelot didn’t have any big hits in 1962 and, furthermore, he’d already been a stage star for a few years, so that he would beat out the Four Seasons, Allan Sherman, the New Christy Minstrels and Peter, Paul and Mary still seems odd.