Top 10 Most Underwhelming Grammy Winners

These Grammy victories were probably not that well-deserved, whether in retrospect or at the time of the win. There were often much better songs, albums, or artists nominated in the same categories.
The Top Ten
1 Macklemore & Ryan Lewis Best New Artist, Best Rap Album (The Heist), Best Rap Song, and Best Rap Performance ("Thrift Shop")

No disrespect to Macklemore, but I think Kendrick definitely should've won at least one Grammy in 2014. Plus Macklemore's chart success significantly declined after 2013, whether solo or with Ryan Lewis.

2 Milli Vanilli Best New Artist

They won Best New Artist in 1990, but after it was revealed they were lip-syncing and not performing vocals on their songs, they were stripped of their Grammy, and rightfully so.

Absolute proof that trendy good looks and dancing ability are far more important than musical talent when it comes to the Grammys.

It's actually kind of cool that these two nitwits were able to fool the oh-so-sanctimonious Grammy voters.

3 Layla (Unplugged) - Eric Clapton Record of the Year, Album of the Year, Song of the Year, Best Pop Vocal Performance - Male, Best Rock Vocal Performance - Male, and Best Rock Song.

"Layla" will always be a rock classic from 1970, but having its acoustic rendition win Best Rock Song over Nirvana's iconic "Smells Like Teen Spirit", which is arguably the most definitive rock song of the 90s, is just an insult.

4 Christopher Cross Record of the Year, Album of the Year, Song of the Year (all for "Sailing"), Best New Artist, and Best Arrangement Accompanying Vocalist(s)

He swept everyone in four major categories in 1980, and it's still a mystery how he won all these awards. He was everywhere in the late 70s/early 80s, but he's not as iconic as Pink Floyd, who definitely should've won Album of the Year (with The Wall, for crying out loud).

5 Cardi B Belcalis Marlenis Almánzar (born October 11, 1992), known professionally as Cardi B, is an American rapper. Born and raised in New York City, she became an Internet celebrity by achieving popularity on Vine and Instagram. From 2015 to 2017, she appeared as a regular cast member on the VH1 reality television... read more

I think Cardi B deserved her Best Rap Album win in 2019. She had fierce competition indeed (including Travis Scott, the late Mac Miller, and Pusha T), but I feel like some people are mad because she's a female rapper or because they are upset over Mac Miller's loss (no disrespect to Mac Miller, of course).

6 Genius Loves Company - Ray Charles Album of the Year and Record of the Year

We all love Ray Charles, and his death was a significant loss, but this Grammy win feels more like a lifetime achievement award. Also, Kanye West's "The College Dropout" definitely would have deserved to win.

7 A Taste of Honey

They won Best New Artist over Elvis Costello, who definitely should've won considering he had a longer career. ATOH, on the other hand, are one-hit wonders, and disco was beginning to die out in 1979.

8 Taylor Swift Taylor Alison Swift is an American singer-songwriter. She was born on December 13, 1989, in Reading, Pennsylvania. Swift is best known for writing personal songs and has won 13 Grammy Awards... read more
9 Two Against Nature - Steely Dan Album of the Year, Best Pop Vocal Album, Best Engineered Album - Non-Classical, and Best Pop Performance by a Duo or Group with Vocals (for the single "Cousin Dupree")

Even though Steely Dan were no longer relevant in the early 2000s, this album won Album of the Year over Eminem's "The Marshall Mathers LP" and Radiohead's "Kid A" in 2001. These two albums have become cult classics since, so one of these definitely should've won in retrospect. I guess the Grammys didn't want Em to win because of homophobic slurs in his lyrics. And besides, GLAAD was protesting against Eminem during that ceremony, and he responded by inviting Elton John onstage for a performance that has since become iconic.

10 Crest of a Knave - Jethro Tull Best Hard Rock/Metal Performance Vocal or Instrumental

This album won Best Hard Rock/Metal Performance in 1989 over Metallica, who definitely should have won because not only did they rule metal in the late 80s, but also because Jethro Tull is anything but metal.

The Contenders
11 Who Let the Dogs Out - Baha Men Best Dance Recording

It won Best Dance/Electronic Recording in 2001 when most of the other nominated songs, if not all, were more deserving. If you're wondering, the other nominees were Eiffel 65's "Blue (Da Ba Dee)", Enrique Iglesias's "Be With You", Jennifer Lopez's "Let's Get Loud", and Moby's "Natural Blues" (which would have deserved it most). "Who Let the Dogs Out" is a fun and catchy song, but a lot of publications consider it to be one of the most annoying songs of all time as well.

12 River: The Joni Letters - Herbie Hancock Album of the Year and Best Contemporary Jazz Album

It won Album of the Year in 2008 over Amy Winehouse and Kanye West. It was just a Joni Mitchell tribute album, while Amy Winehouse's Back to Black was a game-changing record that is considered a classic to this day.

13 O Brother, Where Art Thou? - Various Artists

This soundtrack album is by no means bad, but the 2002 Album of the Year award should've gone to OutKast's classic album "Stankonia" or U2's massive comeback album "All That You Can't Leave Behind". Soundtrack albums are something for the Oscars or a specific Grammy category.

14 Paula Cole

Does anybody remember this singer from the late 90s? She may be known for songs like "Where Have All the Cowboys Gone?" and "I Don't Want To Wait", but she still won Best New Artist in 1998 over Puff Daddy, Erykah Badu and Fiona Apple, who have had successful careers and/or garnered critical acclaim in the following years. Paula Cole, on the other hand, faded into irrelevance, despite "I Don't Want to Wait" being used as the theme song for Dawson's Creek, which lasted 6 seasons between 1998 and 2003. At least she made a legacy out of the series despite her name having been forgotten about.

15 Winchester Cathedral - New Vaudeville Band

How this novelty song won Best Rock & Roll Recording in 1966 over classic songs such as "Eleanor Rigby" by The Beatles and "Good Vibrations" by The Beach Boys is still a mystery to this day.

16 Off the Wall - Michael Jackson
17 Falling Into You - Celine Dion

Despite its massive success, Falling Into You's Album of the Year win in 1997 still feels underwhelming to this day. 'The Score' by The Fugees definitely should've won in retrospect because that album was really groundbreaking for its time and is considered one of the greatest albums of all time by publications such as Rolling Stone. As for 'Falling Into You', it's a good album but it suffers the same flaws as many Céline Dion albums: it's bloated, too long and slightly unfocused. At least it has great singles and a few good deep cuts.

18 Norah Jones Norah Jones is an American singer, songwriter, pianist & actress. She won several awards and sold more than 45 million records worldwide. Billboard named her as the top jazz artist of the 2000–2009 years.
19 Jethro Tull Jethro Tull are a British rock group, formed in Luton, Bedfordshire, in December 1967. Initially playing blues rock, the band soon developed its sound to incorporate elements of British folk music and hard rock to forge a progressive rock signature.
20 Stay High - Brittany Howard Best Rock Song
21 Beyonce Beyoncé Giselle Knowles-Carter, is an American singer and actress, who started out in the popular pop/r&b girl group Destiny's Child. They had multiple top 5 hits such as "No, No, No", "Say My Name", "Bills, Bills, Bills", "Survivor", "Independent Women", "Bootylicious", and "Jumpin', Jumpin" from... read more
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