Intro
Andre 3000's "Hey Ya" Performance
25. Andre 3000's "Hey Ya" Performance
Year: 2004
When the zanier half of OutKast performed his 2003 solo smash live on the Grammys, he succeeded in turning the stage into one big green party. Unfortunately, he failed to make the song sound good, taking a wild yet smooth jam and turning it into a screamfest.
Jethro Tull Winning Best Hard Rock/Metal Performance
24. Jethro Tull winning Best Hard Rock/Metal Performance
Year: 1988
Everyone thought Metallica, who basically owned the metal genre, would win in the new category. How could they not? But as usual, the Grammys found a way, giving the award to a band that peaked in 1971 and that boasts a flute-playing lead singer. A flute!
Christina Aguilera Stumbling On Stage
23. Christina Aguilera Stumbling On Stage
Year: 2011
After tearing the roof off the joint during an Aretha Franklin tribute, Xtina almost blew out her ankle trying to walk of the stage in high heels. Ow!
Arrested Development Winning Best New Artist
22. Arrested Development Winning Best New Artist
Year: 1993
Though the competition wasn't all that strong (shout to Billy Ray Cyrus and Kriss Kross), we've still got a feeling that the only reason A.D. took home this award was because they represented "positive rap" and not that frowned-upon gangsta stuff that was killing (literally?) in the early '90s. Word to Mr. Wendel.
Beyonce's 4 getting snubbed
21. Beyonce's 4 getting snubbed
Year: 2012
Not only was Queen B's fourth album not nominated for Album of the Year. Her soulful set wasn't even gifted with a nod for Best Contemporary R&B Album. Maybe it didn't do her usual chart-topping numbers, but it was a damn good album. It's certainly better than most of the R&B records that came out during 2011.
U2 Winning Song of the Year
20. U2 Winning Song of the Year
Year: 2006
No disrespect to Bono and crew, but we're not even sure "Sometimes You Can't Make It On Your Own" was the best song on U2's album How to Dismantle an Atomic Bomb. Meanwhile Mariah Carey's "We Belong Together" and John Legend's "Ordinary People" (also nominated that year) are two of the best love songs of the last decade. Where's Kanye when you need him?
"Winchester Cathedral" Winning Best Rock & Roll Recording
19. "Winchester Cathedral" Winning Best Rock & Roll Recording
Year: 1966
How a weak novelty rock cut by The New Vaudeville Band (we had to look them up, too) beat out classics from The Beatles ("Eleanor Rigby") and The Beach Boys ("Good Vibrations"), we'll never know.
Guru's Death Being Totally Ignored
18. Guru's Death Being Totally Ignored
Year: 2011
When Gang Starr's Keith "Guru" Elam died of complications from cancer, the hip-hop community felt the pain. To add insult to injury, the Grammys failed to acknowledge his passing in 2011 during their annual salute to the dearly departed. Apparently so many musicians died that this hip-hop immortal didn't make the cut for geting mentioned on the air. Whatever.
Destiny's Child Changing Members Before Their Grammy Appearance
17. Destiny's Child Changing Members Before Their Grammy Appearance
Year: 2000
With two nominations for their smash hit "Bills, Bills, Bills," D.C. was quickly becoming girl-group powerhouse. But when a dispute over dollar bills led to the departure of LaToya Luckett and LaTavia Robertson, the group that showed up at the Awards was not the group who sang on the record. Can you say "awkward"?
Herbie Hancock Winning Album of the Year over Amy Winehouse & Kanye West
16. Herbie Hancock Winning Album of the Year over Amy Winehouse & Kanye West
Year: 2008
Both Amy Winehouse's Back to Black and Kanye West's Graduation were up for the award but lost to Herb. Granted, Herbie Hancock's tribute to Joni Mitchell was a solid piece of work. But good grief, Amy's record was a game-changer. And we totally wouldn't have minded if Kanye stormed the stage to claim the gramophone that year.
Pearl Jam Ethering The Grammys In Their Acceptance Speech
15. Pearl Jam Ethering The Grammys In Their Acceptance Speech
Year: 1996
One of the worst things that can happen as host is having a guest who undermines the party. That's exactly what Pearl Jam lead singer Eddie Vedder did when his group scored a Best Rock Performance win for "Spin the Black Circle." Explaining that the only reason he showed up to the Grammys was because his dead dad would've enjoyed it, Vedder gave the following underwhelming endorsement: "I don't know what this means. I don't think it means anything. That's just how I feel." Gangster.
Steely Dan Beating Radiohead & Eminem for Album of the Year
14. Steely Dan Beating Radiohead & Eminem for Album of the Year
Year: 2001
Eminem's sophomore set The Marshall Mathers LP and Radiohead's Kid A lost to this? Steely Dan has several great albums, but Two Against Nature is not one of them. Given the choice of old and mediocre versus now and cool, the Grammys always lame out.
Natalie Cole Winning Best New Artist
13. Natalie Cole Winning Best New Artist
Year: 1976
KC and the Sunshine Band should've taken this one home. Nat's daughter dropped a nice debut album but her big hit single was basically a karaoke record with her pops. But KC and co. took disco soul to another level.
Aliison Krauss & Robert Plant winning Record of The Year
12. Aliison Krauss & Robert Plant winning Record of The Year
Year: 2009
You could have eenie-meenie-miny-moed between the other contenders in the category ("Chasing Pavements" by Adele, "Viva la Vida" by Coldplay," "Bleeding Love" by Leona Lewis, and "Paper Planes" by M.I.A.) and picked a song better than this duo's tired cut.
The O Brother Where Art Thou Soundtrack Wining Album of the Year
11. The O Brother Where Art Thou Soundtrack Wining Album of the Year
Year: 2002
This would have been a better fit for the Oscars. This Grammy should have gone to Outkast for Stankonia, but even U2's All That You Can't Leave Behind would have been better than this Hollywood spin on country music. Oh brother is right.
"SOY BOMB" man crashing Bob Dylan's Performance
10. "SOY BOMB" man crashing Bob Dylan's Performance
Year: 1998
Before Lil Mama crashed Jay-Z and Alicia Keys at the MTV Awards, there was this creep at the Grammys. He had been hired to stand in the background with some other paid extras and nod his head while the legendary Bob Dylan ran through "Love Sick." Instead he ripped off his shirt and copped a cool 30 seconds of air time doing the robot with the words "SOY BOMB" written on his chest. Dork.
Ray Charles Winning Album of the Year
9. Ray Charles Winning Album of the Year
Year: 2005
Of course Ray's a legend and all. But there's no way that his album of duets—his 250th LP, and the last released before his death—should have topped Usher's colossal Confessions and Kanye West's epic debut, The College Dropout.
Toto Winning Album and Record of the Year
8. Toto Winning Album and Record of the Year
Year: 1983
A band named after Dorothy's mutt in The Wizard of Oz somehow dogged their fellow nominees Billy Joel and Paul McCartney with a mediocre set and then proceeded to tank career-wise.
A Taste of Honey beating Elvis Costello For Best New Artist
7. A Taste of Honey beating Elvis Costello For Best New Artist
Year: 1979
We know Honey's "Boogie Oogie Oogie" was one of the last disco records to blow, but they were one-hit wnders, while Costello would go on to create an amazing body of work. His reckless, yet cool brand of rock ("Pump It Up") should have earned him this award.
Christopher Cross Sweeping Four Major Awards
6. Christopher Cross Sweeping Four Major Awards
Year: 1981
Two words: Pink. Floyd. How Chris Cross whopped up on several heavyweights—including Pink Floyd's rock classic The Wall—still boggles the mind. Album of the Year, Song of the Year, Record of the Year, and Best New Artist—really?
Paula Cole Winning Best New Artist over Puff Daddy, Fiona Apple, & Erykah Badu
5. Paula Cole Winning Best New Artist over Puff Daddy, Fiona Apple, & Erykah Badu
Year: 1998
Somehow this singer named Paula Cole managed to best Bad Boy boss Puff Daddy and oddball temptresses Erykah Badu and Fionna Apple. They got the last laugh, though—they're all still relevant. Apparently Paula sang a song called "Where Have All The Cowboys Gone?" But the real question is "Where Has Paula Cole Gone?"
Clueless Nominees for Best Rap Performance
4. Clueless Nominees for Best Rap Performance
Year: 1989
The first year rap was recognized by the Grammys, the award presentation was not televised. And while we're not mad a DJ Jazzy Jeff & The Fresh Prince—who won for "Parents Just Don't Understand"—how did J.J. Fadd receive a nomination while Big Daddy Kane, KRS-One, and N.W.A—who had just dropped Straight Outta Compton—got nada? No wonder Will Smith boycotted the Grammys that year.
Nirvana's "Smells Like Teen Spirit" Losing For Best Rock Song
3. Nirvana's "Smells Like Teen Spirit" Losing For Best Rock Song
Year: 1993
Nirvana's groundbreaking classic lost to Eric Clapton's "Layla," which was an amazing song—back in 1970 when it was first released. Nirvana's "Teen Spirit" represented the sound of the grunge movement, which was exploding in 1993. (And the song still knocks today, by the way). Eric Clapton's "Unplugged" version of "Layla" was a soundtrack for suburban soccer moms. #EpicFail.
Frank Sinatra Not Being Allowed To Perform
2. Frank Sinatra Not Being Allowed To Perform
Year: 1994
"Old Blue Eyes" should've just been glad to get the Grammy Legend Award, right? Wrong! This is Frank Sinatra we're talking about. He wanted to perform, too. But the Recording Academy didn't allow it. So when Sinatra accepted his award, he said thanks to many and proceeded to give the rest a piece of his mind. And then soon after he said he was "angry" and "hurt," they cut to a commercial. Don't dis the don.
Milli Vanilli Winning Best New Artist
1. Milli Vanilli Winning Best New Artist
Year: 1990
Talk about a fail! Not only was the music they claimed bad in general, it wasn't even theirs. Lip-sync fail.
