The Grammy Awards' Biggest Mistakes

It's always easy to second-guess award show winners and losers, especially in hindsight, but the Grammy Awards has earned itself a particular reputation for occasionally picking the wrong horse -- or at least picking it for the wrong race. So to help avoid getting your yearly Grammy-hopes too high, we've rounded up a dirty dozen "um, seriously, WTF?" selections from awards shows past.

1965 Best Record: João Gilberto & Stan Getz, 'Girl From Ipanema'
Gilberto and Getz are cool and all, and 'Ipanema' is a great single, but the jazz duo also won Best Album while Beatlemania was swamping the bossa nova craze. The Beatles made do with Best New Artist and Best Vocal Performance by a Group despite clocking five (!) chart-topping albums and six (!!) US No. 1 singles in '64, including 'I Want to Hold Your Hand,' 'She Loves You,' 'Can't Buy Me Love' and 'A Hard Day's Night.' The following year, the Fab Four lost all 10 nominations, but by 1968 voters would bestow best album on their psychedelic masterwork 'Sgt Pepper's Lonely Hearts Club Band.'

1967 Best Contemporary Rock & Roll Recording: New Vaudeville Band, 'Winchester Cathedral'
At the height of the 1960s counterculture, voters had one of the strongest categories in its history to contend with, including such nominated future classics as the Beach Boys' hang-loose anthem 'Good Vibrations,' the Mamas & the Papas' timeless 'Monday Monday,' the Monkees' Beatlesque earworm 'Last Train to Clarksville' and the actual Beatles' beloved 'Eleanor Rigby.' They chose the New Vaudeville Band, a studio concoction that rocked the Roaring '20s sound down to the last "vo-de-o-doh" crooned through a megaphone.

1979 Best New Artist: A Taste of Honey
Admittedly, the Best New Artist prize is a crap shoot. Without hindsight, the Grammy voters couldn't have known that, say, Elvis Costello and the Cars would go on to become legendary acts with countless hits and boundless acclaim. But still, they passed over these post-punk upstarts in favour of the L.A. disco outfit that brought 'Boogie Oogie Oogie' to the dance floor -- and little else since.

1986 Record of the Year: USA for Africa, 'We Are the World'
With the African famine raging, American pop stars banded together to one-up British pop stars with this charity single penned by Michael Jackson and Lionel Richie. It was a great cause, without question, but the song itself could hardly compare to its category companions: Dire Straits' 'Money for Nothing,' Don Henley's 'Boys of Summer,' Huey Lewis and the News' 'Power of Love' (c'mon, it was the 'Back to the Future' theme!) and the robbed record of the year, Bruce Springsteen's arms-up anthem 'Born in the USA.'



1989 Best Hard Rock Recording: Jethro Tull, 'Crest of a Knave'
Giving the flute-flouting '70s prog-rockers this post-peak award is one of the most infamous flubs, with 'Entertainment Weekly' later naming it the Grammys' biggest upset. Not only were Jethro Tull not "hard" -- the album's called 'Crest of a Knave' for frak's sake -- but they beat out the likes of AC/DC, Jane's Addiction and even Metallica's '... And Justice for All.' The crowd booed, presenter Alice Cooper blushed, and when Metallica finally did win a few years later, drummer Lars Ulrich sarcastically quipped, "We gotta thank Jethro Tull for not putting out an album this year."

1990 Best New Artist: Milli Vanilli
After every presentation, critics and fans like to grouse about who did or didn't deserve to win. But only once has the recording academy actually admitted their screw-up. Perhaps blinded by Milli Vanilli's sales figures -- or at least by Rob and Fab's cheekbones and braids -- the former Euro models had their award taken back once it was revealed they didn't sing a note on their recordings. (Yes, before Auto-tune, nonsingers had to take more extreme measures). The worst part of the scandal was that it denied the award to a quartet of cool nominees: Neneh Cherry, Indigo Girls, Tone Lōc and Soul II Soul.



1990 Best Rap Performance: Young MC, 'Bust a Move'
This was just a bad year all around. 'Bust a Move' was a fun little hip-pop song that has endured for two decades -- most recently showing up on 'Glee' -- and made sense trumping DJ Jazzy Jeff and the Fresh Prince's silly 'I Think I Can Beat Mike Tyson' and Tone Lōc's 'Funky Cold Medina' (which Young MC also wrote). There's even an argument to be made over De La Soul's 'Me, Myself & I.' But let's get real -- Public Enemy's agit-rap call to arms 'Fight the Power' was a revelatory single that still stands tall as one of music's greatest (and funkiest) political statements and perhaps hip-hop's finest moment.

1992 Best Album: Natalie Cole, 'Unforgettable ... With Love'
You probably remember the early '90s as the birth of the alt-rock revolution, the moment when Nirvana knocked Michael Jackson off the top of the charts and their Seattle brethren stormed through the now-open gates. Grammy remembers the year differently, deciding the best music came courtesy of a tear-jerking Natalie Cole singing over an ancient tape recording from her long-deceased famous father. Oh well, whatever, nevermind.

1995 Best Album: Tony Bennett, 'MTV Unplugged'
Yes, Mr. Bennett is a legend and he's surely earned his share of Grammy gold, but to take Best Album in one of the greatest years in recorded music history? Let's put it this way -- these weren't even nominated: Nine Inch Nails, 'Downward Spiral'; Soundgarden, 'Superunknown'; ' Tori Amos; 'Under the Pink'; Green Day, 'Dookie'; Pavement, 'Crooked Rain, Crooked Rain'; Hole, 'Live Through This'; Beastie Boys, 'Ill Communication'; Nas, 'Illmatic'; Oasis, 'Definitely Maybe'; R.E.M., 'Monster'; Offspring, 'Smash'; Blur, 'Parklife'; Weezer, 'Weezer' (the Blue Album); Pearl Jam, 'Versus'; Notorious B.I.G., 'Ready to Die'; A Tribe Called Quest, 'Midnight Marauders'; Wu-Tang Clan, 'Enter the Wu (36 Chambers)'; and the 'Pulp Fiction' soundtrack. Hell, if they had to give it to another 'Unplugged' album (Eric Clapton also inexplicably won the title in 1993), a little band named Nirvana released an eminently more relevant one.

2001 Best Album: Steely Dan, 'Two Against Nature'
Steely Dan's head-scratcher of a winner beat the real album of the year -- Eminem's 'The Marshall Mathers LP.' This stone-cold classic was as controversial as it was brilliant -- the occasional gay-baiting and misogynistic lyrics were offset by mind-boggling wordplay and internal rhyme schemes -- and is as catchy as it is grotesque. It's also one of the last full-length albums to so dominate pop culture before the iPod made the single king again. Oh, and there was another classic album on the list: Radiohead's 'Kid A.' Two against nature, indeed.



2001 Best Dance Recording: Baha Men, 'Who Let the Dogs Out'
The rave scene was on its downward slope at the turn of the millennium, sure, but there were still a raft of great dance tunes, like Madonna's Mirwais-produced 'Music,' Fatboy Slim's 'Weapon of Choice' (the one with the video of Christopher Walken dancing in air), Moloko's house classic 'Sing It Back,' Le Tigre's 'Deceptacon,' Basement Jaxx's 'Red Alert' or Moby's 'Natural Blues.' Only the latter even landed a Grammy nod, and the winner somehow was Baha Men's 'Who Let the Dogs Out,' a song that would later win Spinner's own worst song ever award.

2004 Best Album: OutKast 'Speakerboxxx/The Love Below'
It's a classic award show move to honour an artist for a lesser work after missing the boat during its truly deserving albums. In this case, the Atlanta hip-hop duo should have been recognized for their groundbreaking 'Stankonia' but instead took home the gold for what was essentially a pair of solo albums, which boasted a song of the year ('Hey Ya!') but, in hindsight, little else. A similar move would happen in 2006, when U2 won for the relatively weak 'How to Dismantle an Atomic Bomb' as reparations for not taking home the prize for truly deserving efforts like 'Achtung Baby.' And fans of both Kanye West and Amy Winehouse feel the same about Herbie Hancock's 2008 Best Album win for his jazzy Joni Mitchell tribute 'River: The Joni Letters.'