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The New Vaudeville Band, the 1960s novelty pop band, won Best Contemporary Rock & Roll Recording for their song "Winchester Cathedral" in 1967. They beat out "Monday, Monday" by The Mamas & the Papas, "Eleanor Rigby" by The Beatles, and "Good Vibrations" by The Beach Boys—all of which are considered classics today.

It wasn't that José Feliciano was undeserving of the Best New Artist award in 1969, but people were surprised that he beat Cream—among the best rock bands of all time. Feliciano's lasting contributions include singing the most famous version of "Feliz Navidad."

In 1984, won Album of the Year. It was a deserved award in many fans' eyes. However, the competition may not have been entirely fair. Prince's classic "1999" wasn't even nominated. That album, in which Prince plays almost all of the instrumentals himself, secured his place among music's greats and is largely considered .

In 1989, the Grammys introduced a new category to indicate that they were hip to the times: Best Hard Rock/Metal Recording. Among the nominees were Metallica, Iggy Pop, AC/DC, and Jane's Addiction. When Jethro Tull—a progressive rock band that heavily featured flute—won, many in the crowd started laughing. Today, it's still considered a hilarious bungle, even by the members of Jethro Tull.

Milli Vanilli was awarded the Best New Artist award in 1990. But when the pop duo admitted that they hadn't actually sung any of their songs themselves, both on their album or in concert, . The pair became a laughing stock and, despite trying to stage a comeback, could not regain their footing before 32-year-old member Rob Pilatus died from an overdose in 1998.

The year was 1991, and Sinéad O'Connor was nominated for Best Female Pop Vocal Performance, Best Alternative Music Performance, and Record of the Year. Though she won the Best Alternative Performance category, she was not there to receive it, as she withdrew herself from the ceremony due to its "."

Eric Clapton is an undeniable music legend—as well as the lead guitarist of the aforementioned Cream—and his song, "Layla," has stood the test of time. However, in 1993, it was an acoustic cover of that song—which, by then, was two decades old—that beat out Nirvana's "Smells Like Teen Spirit" for Best Rock Song. Today, "Teen Spirit" is considered a touchstone of the '90s and among Nirvana's best works.

Many artists are ecstatic to win their first Grammy Award, but that was not the case for Pearl Jam's lead man, Eddie Vedder. When the group won Best Hard Rock Performance in 1996, , "I don't know what this means. I don't think it means anything. That's just how I feel."

Though his nonchalance confounded some, Pearl Jam went on to achieve great acclaim. In 2000, Vedder dissed the Grammys once again at a 10-year anniversary performance for his band in Las Vegas, , "I would never do this accepting a Grammy or something."

The year is 2000. The question on everyone's mind: Which pop princess will take Best New Artist, Christina Aguilera or Britney Spears? By night's end, , signaling a reign that would see the pop star dominating the Grammy Awards for years to come.

When country singer Shelby Lynne won Best New Artist in 2001, fans felt that maybe it was a tad late for her to be considered a "new" artist. She had already been recording for years. As she joked in her acceptance speech, it took her "." Since then, she's released several more studio albums and dozens of singles.

Kanye West famously interrupted Taylor Swift's Video Music Awards speech in 2009. Perhaps he was inspired by another rapper who pulled a similar stunt back in 2004.

When alternative rock band Evanescence won Best New Artist and began their speech, 50 Cent, who had also been nominated for the award, jumped on stage and paraded around the band before making his way back to his seat. Evanescence singer Amy Lee took it in stride, joking about it. Today, it's still considered an oversight that 50 Cent lost, considering he was —and didn't win any.

The 2005 Grammy Awards saw 10 nominations for Kanye West's "The College Dropout," the most nominations for any artist there. While West secured three wins, there were two major oversights. First, his defeat by Maroon 5 for Best New Artist. Second, and perhaps most egregiously, his loss to Ray Charles for Album of the Year. Charles had just died, and the award given to his record "Genius Loves Company" was seen as to the music legend.

By 2008, Amy Winehouse's second (and final) studio album, "Back to Black," had been out for several years and was considered some of the best material for that year's Grammy Awards. Winehouse left rehab to perform for the ceremony via satellite and won five awards, including Song of the Year and Best New Artist. But in a surprise twist, Best Album went to the long-established Herbie Hancock, a jazz artist who had released an album of reimagined Joni Mitchell songs.

Hip-hop fans were none too happy when Macklemore beat out Kendrick Lamar for Best Rap Album in 2014. They were even more perplexed when Macklemore with Lamar to social media, wherein he apologized for winning the award he felt Lamar deserved. Was he being honest or pandering to public opinion?

No matter: Lamar went on to win the award at the 2016 ceremony for "To Pimp a Butterfly" and in 2018 for "Damn," which even won him the Pulitzer Prize for Music.

Adele's reaction to winning the Grammy for Album of the Year in 2017 for "25" wasn't elation. In fact, she admitted "" when she was announced the winner. On stage, she apologized to Beyoncé, who she said deserved the award for her album "Lemonade."