Home Music Music Lists

20 Awesome Moments in Retro Grammy History

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

brooke shields michael jackson emmanuel lewis

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

Ron Galella/WireImage

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.

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.