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20 Awesome Retro Moments in Grammy History

Ahead of the 57th Annual Grammy Awards this weekend, we look at back at some of the best moments from 1971-1991, including a vampiric David Bowie, awkward Milli Vanilli and confusing Bob Dylan.

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.

1. Record of the Year (1971): Simon and Garfunkel Nod Awkwardly

Who needs to hear the winners give a speech when you can have the 5th Dimension turn a standard reading of the Record of the Year nominees into a song? Nineteen-seventy-one was a pretty incredible year, with “Let It Be,” “Fire and Rain” and “Bridge Over Troubled Water” duking it out. Simon and Garfunkel won, though Garfunkel’s entire speech was “thank you” and Simon just nodded his head. The duo also won Album of the Year, Song of the Year and Best Contemporary Song that night, so they may have been a little talked out. They had also broken up by this point, so maybe they also just didn’t feel like spending that night together at the podium. 

2. The Carpenters (1972): Superfast “Superstar”

The Carpenters won Best New Artist in 1970 (over Elton John, Anne Murray, Melba Moore and, hilariously, the Partridge Family), and two years later they were invited back to perform “Superstar.” The song — about a groupie desperately in love with a rock star after a one-night stand — was written by Leon Russell and initially recorded by Delaney and Bonnie, but the Carpenters made it a huge hit. Even in 1972, Grammy producers were careful about time and made them perform a condensed version of the song.

3. Best R&B Vocal Performance Male (1973): Nilsson and Ringo Goof Off

It’s possible that Harry Nilsson and Ringo Starr were having one of their rare sober nights at the 1973 Grammys, but odds are high that wasn’t the case. It barely matters. The two friends walked onstage like the Monkees and delivered a great skit where they spoke all their scripted banter in unison. It’s absolutely hysterical. They also gave out the award for Best R&B Vocal Performance, Male to Billy Paul for “Me and Mrs. Jones.”

4. Record of the Year (1975): Simon Zings Garfunkel

Here’s a weird moment in music history: Paul Simon, John Lennon and Andy Williams were presenting the award for Record of the Year at the 1975 Grammys, but winner Olivia Newton-John wasn’t around. For reasons that surely made sense at the time, Art Garfunkel accepted on her behalf. “I thought I told you to wait in the car,” Paul said when he walked onstage. Ouch.

5. Best R&B Female Vocalist (1975): Bowie Leaves His Casket

David Bowie did some incredible work in 1975, but he was also doing so much cocaine, he began thinking his television was talking to him. He claims to have little memory of anything that happened that year and he looks like a vampire in this clip from the 1975 Grammys. He presented the award for Best R&B Female Vocalist to Aretha Franklin. “Wow, this is so good I could kiss David Bowie,” said Franklin. “And I mean that in a beautiful way, because we just did.”

6. Starland Vocal Band (1977): Grammys Stage a Key Party

For one brief shining moment in 1977, the Starland Vocal Band seemed like they had a bright future. The two real-life couples wrote a lovely ode to mid-day boning, and before they knew it, they had a hit all over the radio and a Grammy for Best New Artist. They sang “Afternoon Delight” at the ceremony, but never had anything close to a hit ever again and broke up by 1981.

7. Album of the Year (1978): The Mac Beats the Force

The competition was stiff for Album of the Year in 1978. Steely Dan’s Aja was up against Fleetwood Mac’s Rumours, the Eagles’ Hotel California, James Taylor’s JT and the soundtrack to Star Wars. Crosby, Stills and Nash handed out the award to Fleetwood Mac. You can almost smell the cocaine.

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.

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. Synthesiser 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.

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.