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20 Awesome Moments in Retro Grammy History

From a vampiric David Bowie to awkward Milli Vanilli, relive Grammy madness from 1971-1991

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We look back at strange, funny and just plain awkward Grammy moments from the Seventies through the Nineties.

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No major awards show gets maligned more than the Grammys. They’ve certainly invited criticism by refusing to give Bob Dylan a single award until 1979 and deciding Jethro Tull were more metal than Metallica, but almost every musician still dreams of winning a golden gramophone. The ceremony has changed a lot over the past six decades, gradually shifting from a formal event where men in tuxedos read dry speeches to the bombastic, performance-driven spectacular of today. We combed the archives to find the weirdest and coolest moments from the Grammys’ distant past.

8. The Doobie Brothers (1980): Yacht Rock Takes Over

The Grammys went through an intense Yacht Rock phase in the early 1980s — they even managed to get the Doobie Brothers into tuxedos for this performance of "What a Fool Believes" from the 1980 broadcast. The band scooped up Record of the Year and Song of the Year that night for that very tune. 

9. Best New Artist (1981): Christopher Cross Sails Away With Grammy Gold

The 1981 Grammys were all about Christopher Cross. In a feat never matched before or since, the Yacht Rock king walked away with Record of the Year, Album of the Year, Song of the Year and Best New Artist. He beat out the Pretenders, Irene Cara, Robbie Dupree and Amy Holland for the latter award. Sadly, the evening was the peak of his career, though later that year he did release "Arthur's Theme (Best That You Can Do.)" He does remain a popular live act and his performance of "Ride Like the Wind" with the Roots on Late Night With Jimmy Fallon a couple of years back was one of the great moments in the show's history. The dude is a sick guitarist. Seriously. 

10. Song of the Year (1982): Bette Davis Eyes a Grammy Win

Somebody had the great idea in 1982 to have all the Song of the Year nominees play condensed versions of their songs at the ceremony. Check out Burt Bacharach and Christopher Cross singing "Arthur's Theme," Bill Withers, Ralph MacDonald and William Salter plaing "Just the Two of Us," Lionel Richie doing "Endless Love" and Jackie DeShannon and Donna Weiss attempting "Bette Davis Eyes." They wrote the song, but can't quite sing it like Kim Carnes. John Denver gave them the award anyway. 

11. Best New Artist (1983): Men at Work’s Misplaced Confidence

"This award just isn't for the star of today," said Lily Tomlin as she introduced the Best New Artist nominees at the 1983 Grammys. "But for someone who, just possibly, might be a star for years to come." Men at Work beat out Asia, Jennifer Holiday, the Human League and Stray Cats. "We are the men," Colin Hay said in his speech. "And we'll see you again." They broke up just three years later. 

12. Song of the Year (1984): Stevie Wonder Helps Bob Dylan Read

One of these two men is blind, but you'd never guess it was Stevie Wonder and not Bob Dylan from watching this 1984 clip where the duo announces the categories for Song of the Year. Dylan doesn't seem to realize he has to read the names of the nominees, occasionally forcing Wonder to jump in and help. This was also the year where Michael Jackson took Brooke Shields and Emmanuel Lewis as his guests. Jackson was dressed up like the captain of the disco navy, but he looks pretty nervous as his name was read. He lost to the Police, who were in Australia playing their final headlining gigs until their 2007 reunion tour. 

Bonnie Tyler

13. Bonnie Tyler (1984): Total Eclipse of the Hair

Bonnie Tyler's classic "Total Eclipse of the Heart" was nominated for Best Female Pop Vocal at the 1984 Grammy Awards, but she lost out to Irene Cara's "Flashdance…What a Feeling." She still delivered a pretty great rendition of the song on the telecast, rocking the most 1984 haircut ever captured on film. 

14. The Eurythmics (1984): Annie Lennox Inspires Lady Gaga

Twenty-seven years before Lady Gaga came to the MTV Video Music Awards dressed as her Ralph Macchio-esque character Jo Calderone, Annie Lennox pulled a very similar move during the Eurythmics' performance of "Sweet Dreams" at the 1984 Grammys. (The similarities between the two characters are pretty striking.) The Eurythmics split up years ago, but are going to reunite this year to honor the Beatles.

15. Synthesizer Showdown (1985)

If there's one instrument that defined the sound of the 1980s, it was the synthesizer. It's impossible to imagine what the music of the decade would have sounded like had it not been invented. At the 1985 Grammys, Stevie Wonder, Howard Jones, Thomas Dolby and Herbie Hancock joined forces for the mightiest 1980s synth jam ever captured on film. It's a giant mashup of all their hits and needs to be seen to be believed. 

16. Lou Reed/Dion/David Johansen (1988): Punks Praise Doo-Wop

It's hard to hear much of a Dion influence in the sound of the Velvet Underground and the New York Dolls, but Lou Reed and David Johansen had tremendous respect for the music that came out of their native city when they were kids. At the 1988 Grammy's they honored Dion by singing "Teenager in Love" with him. It was a very sweet moment, and further evidence that Reed wasn't as gruff and subversive as his reputation suggested.

17. Best Hard Rock/Metal Performance (1989): Metal Massacre

The Grammys have existed for over 55 years, but when people want to make fun of them they often point to this moment from the 1989 ceremony. It was the first year of the Best Hard Rock/Metal Performance Vocal or Instrumental and Metallica's …And Justice For All and new works by AC/DC, Jane's Addiction and Iggy Pop were up against Jethro Tull's extremely un-metal Crest of a Knave. Tull didn't even bother going to the ceremony, but they won. It caused a complete outrage, and Metallica won next year. But the Grammys have never quite gotten over this embarrassment. 

18. Sinead O’Connor (1989): America Meets Its Match

Most Americans first saw Sinéad O'Connor perform live when the 21-year-old Irish singer played "Mandinka" at the 1989 Grammys. If there was Twitter back then, "bald chick" would have probably been trending in about six seconds. It was the beginning of a very eventful few years for O'Connor. 

Milli Vanilli

19. Milli Vanilli (1990): The Beginning of the End

Technically speaking, nobody won the Best New Artist Grammy in 1990 because Milli Vanilli gave up their trophies after it was revealed they didn't sing a note on their album. Grammy night was the peak of their entire career. Their performance of "Girl You Know It's True" sounded suspiciously like the version on the album, but nobody suspected a thing at the time.

20. Bob Dylan (1991): The Bard Takes His Time, Confuses Everyone

Operation Desert Storm was just weeks old when Bob Dylan was given a Lifetime Achievement Award at the 1991 Grammys. There was supposed to be an all-star tribute to Dylan, but many of the artists backed out, forcing Dylan to play a raggedy, reggae "Masters of War" by himself. He also gave one of the most bizarre speeches of his life. "Thank you," he said. "Well, all right. Yeah. Well, my daddy didn't leave me too much. He was a very simple man, and he didn't leave me a lot. But what he taught me was, is that he did say, 'Son. . .' He said, um. . . [eight-second pause] he said so many things. But he did say, 'It's possible to become so defiled in this world that your own mother and father will abandon you. If that does happen, God will always believe in your own ability to mend your own ways. Thank you.'" All right then.  

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