The 30 Weirdest Grammys Moments of All Time

There’s a good reason why the Grammy Awards coined the term “Grammy Moments” to describe the one-of-a-kind collaborations and elaborate performances that take place during each year’s broadcast. There’s always at least one off-the-wall, meme-able event that becomes part of awards show lore. In previous years, it was John Travolta’s teleprompter problems and Twenty One Pilots’ boxer shorts; other years have given us impractical costumes, head-scratching indie rock wins, and Kanye West trying to jump on stage.

Here are the 30 weirdest Grammy moments of all time.

30. “Who Let the Dogs Out?” wins the Best Dance Recording Grammy (2001)

From a statistical standpoint, “Who Let the Dogs Out?” winning the Grammy for Best Dance Recording in 2001 was an outlier. Baha Men’s barking earworm was the only nominated tune not to grace the Billboard dance charts. (In fact, Enrique Iglesias’ “Be With You” actually hit No. 1.) Aside from that, it beat out Europop phenom Eiffel 65, then-pop superstar Jennifer Lopez, and perennial electronic darling Moby to win the award. The power of the Rugrats in Paris soundtrack (which helped the song become a hit) is strong with this one. —Annie Zaleski

29. Twenty One Pilots delivering a surprisingly sentimental speech in their underwear (2017)

Before they even walked up to accept their Grammy for Best Pop Duo in 2017, Twenty One Pilots stripped down to their boxers, apparently paying tribute to the days when the duo would sit at home and watch the award show in their underwear. In an even more unexpected twist, their speech ended up being surprisingly heartfelt, which just goes to show that good public speaking skills go a long way. —Sam Goldner

28. Gorillaz and Madonna join forces for a lethargic collaboration (2006)

Despite being a cartoon band, Gorillaz have always done an admirable job translating their electro/hip-hop hybrids to a live setting. This 2006 Grammys performance of “Feel Good Inc.” is a notable exception. The animated members seem bored: 2-D, voiced by Blur‘s Damon Albarn, checks his virtual phone during the song, and drummer Russel Hobbs nods off. Even an energetic Madonna showing up to interact with Gorillaz and sing her then-hit “Hung Up” can’t save the lethargic performance. The only redeeming factor is the non-virtual De La Soul coming onstage to reprise their buoyant “Feel Good Inc.” bridge—and Madonna ditching Gorillaz to finish her own song. —AZ

27. Steely Dan winning Album of the Year… in 2001 (2001)

The Grammys have always favored old, safe bets over newer, riskier voices, but this one was just ridiculous. In the same year that Radiohead released Kid A, Eminem released The Marshall Mathers LP, and Beck released Midnite Vultures, the Grammys chose to give Album of the Year to soft-rock vets Steely Dan for Two Against Nature. And this was before it was even cool to like Steely Dan again. —SG