When people think of the Grammys, one of the most common images that comes to mind is of an artist who just swept cradling four or five Grammys in their arms. And while most of these sweeps are for a combination of songs and an album, some musicians have managed to make individual songs iconic enough to warrant four or five Grammys all on their own.
Albeit a short list, some recordings have the distinction of winning that many trophies. Here’s a list of the most awarded songs in Grammy history. For the sake of clarity, this list focuses on specific recordings, meaning that covers of the same songs are not counted on the final tally.
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‘Leave the Door Open’ by Silk Sonic (2022)
Image Credit: John Esparza This smooth R&B jam by Bruno Mars and Anderson .Paak, also known as the superduo Silk Sonic, achieved a clean sweep at the 2022 Grammys. The track took home the two big prizes for Record of the Year and Song of the Year, as well as Best R&B Song and Best R&B Performance (in a tie). It’s the first song to win all four of these prizes, and also the first to pull off a clean sweep in the 2020s.
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‘This is America’ by Childish Gambino (2019)
Image Credit: CBS This acclaimed hip-hop political anthem by Childish Gambino became the first of its genre to win the Grammys for Record and Song of the Year. It won two additional trophies: Best Rap/Sung Performance and Best Music Video.
Funny enough, the song might’ve won five Grammys had it been nominated for Best Rap Song, but at the time the contenders in that category were determined by a nominations review committee and not the full academy membership. “This Is America” is nevertheless the most awarded hip-hop song at the Grammys.
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‘Need You Now’ by Lady A (2011)
Image Credit: Courtesy of Lee More This is the most awarded country recording ever at the Grammys. Lady A’s decade-defining hit took home four awards, including Record and Song of the Year, making it the last country song to take those awards. In addition to its two general field awards, the track took home Grammys for Best Country Song and Best Country Performance by a Duo or Group with Vocals. “Need You Now” is also the only song to win all four of those honors.
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‘We Are the World’ by USA for Africa (1986)
Image Credit: Courtesy Image This star-studded, once-in-a-lifetime classic penned by Michael Jackson and Lionel Richie was a huge success at the Grammys. Of course, that makes sense, as I’m sure a lot of the artists involved were voters themselves. Plus, “We Are The World” represented musicians coming together to do good, which appealed to the recording academy membership made up of musicians.
The track took home Record and Song of the Year, as well as Best Pop Performance by a Duo or Group with Vocals. Perhaps most surprisingly, it won the Grammy for Best Music Video despite the video simply being footage of the artists recording the song in the studio. Alas, it was the year of “We Are The World,” and it took everything it could; its parent album even got nominated for Album of the Year, although it lost.
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‘Bridge Over Troubled Water’ by Simon and Garfunkel (1971)
Image Credit: Columbia Most people know “Bridge Over Troubled Water,” which is arguably the signature song of Simon and Garfunkel. It has been a classic since its release, as it completely ruled the 13th Grammy Awards. The track won Record of the Year, Song of the Year, Best Arrangement Accompanying Vocalist(s), and Best Contemporary Song.
Not only did the song win four awards, but the duo also won for Album of the Year and Best Engineered Album, Non-Classical. The duo’s only loss was for Best Pop Performance by a Duo or Group with Vocals, which likely happened because they submitted the album over the song; you could do that back then since genre album categories didn’t yet exist.
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‘Up, Up, and Away’ by The 5th Dimension (1968)
Image Credit: Getty Images Here’s the most awarded recording ever by the Grammys: “Up, Up, and Away” by The 5th Dimension. It’s the only track ever to win a whopping five Grammy Awards, an especially impressive feat considering this isn’t even a song that could win additional categories like Best Music Video or Best Song for Visual Media like other three-or-more winners.
The iconic hit won Record of the Year, Song of the Year, Best Pop Performance by a Duo or Group with Vocals, Best Performance by a Vocal Group, and Best Contemporary Song. In addition to those five, another version by The Johnny Mann Singers took home an additional Grammy for Best Performance by a Chorus.
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‘Strangers in the Night’ by Frank Sinatra (1967)
Image Credit: Courtesy Image Frank Sinatra’s “Strangers in the Night” is one of his most beloved songs, so it’s no surprise it took the 9th Grammy Awards by storm. The song won Record of the Year, Best Male Pop Vocal Performance, Best Arrangement Accompanying a Vocalist or Instrumentalist, and Best Engineered Recording – Non-Classical. However, “Strangers in the Night” is the only song on this list that did not achieve a clean sweep, as it lost Song of the Year to The Beatles’ “Michelle,” which is a bit unusual considering Sinatra beat the band for Album of the Year.
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‘A Taste of Honey’ by Herb Alpert and the Tijuana Brass (1966)
Image Credit: A&M Records Herb Alpert and the Tijuana Brass’s “A Taste of Honey” was an unusual hit, being a fully instrumental performance. The Alpert version took home four awards at the 8th Grammys: Record of the Year, Best Instrumental Arrangement, Best Instrumental Performance, and Best Engineered Recording – Non-Classical.
Technically the song has won five Grammys, since the original won for Best Instrumental Composition at the 5th Grammys. But since we’re focusing on specific recordings, four it is. As such, Alpert’s “A Taste of Honey” remains the most awarded instrumental recording at the Grammys.
