8 Artists Who Have Won the Three Biggest Grammy Awards in One Night

The Grammy Awards, often regarded as the highest honor in the music industry, has celebrated outstanding achievements across various genres and categories for decades. Since its first award ceremony on May 4, 1959, the Recording Academy has honored and recognized artists, producers, and songwriters every year for their contributions to music. Among the numerous awards, three stand out as its biggest and most prestigious: Album of the Year, Record of the Year, and Song of the Year. 

Winning just one of these Awards is a remarkable feat in itself. However, securing all three in a single night is a rare and historic achievement that has only been achieved nine times in the past 67 years. Only a handful of artists have accomplished this extraordinary milestone, cementing their place in music history. As of the 2025 Awards, these are the eight artists who have achieved the rare “Big Three” sweep at the Grammys. 

Paul Simon

Paul Simon Grammy Awards

Year of Win: 1971

American singer-songwriter and musician Paul Simon is known for his poetic lyrics and innovative approach to folk and rock music. He first gained fame as one half of the duo Simon & Garfunkel, alongside Art Garfunkel, during the 1960s. Together, they became one of the most influential musical acts of their time. After Simon & Garfunkel was disbanded in 1970, Paul Simon embarked on a successful solo career. 

Simon & Garfunkel’s final album, Bridge over Troubled Water, as Simon & Garfunkel is one of the the best-selling albums of all time. Interestingly, Paul Simon received the highest recognition by becoming the first artist to win all three Grammys top awards in a single night. At the 13th Annual Grammy Awards held at Hollywood Palladium on March 16, 1971, their album, Bridge over Troubled Water, won Record of the Year and Album of the Year. Paul Simon, who wrote the single “Bridge over Troubled Water,” also won Song of the Year, making him the first to win the Grammy’s “Big Three” awards.

Carole King

Carole King

Year of Win: 1972

Carol King is an American singer-songwriter and one of the most influential figures in pop music history. She rose to fame in the 1960s as a songwriter, co-writing numerous hits with her then-husband Gerry Griffin. They wrote hits for artists like The Shirelles, Aretha Franklin, and The Monkees. However, she achieved even greater success as a solo artist with her 1971 album Tapestry

Despite her debut album disappointment, Tapestry became her breakthrough album and one of the best-selling albums of all time. King’s deeply personal and emotionally resonant songwriting helped redefine the singer-songwriter genre. At the 14th Annual Grammy Awards on March 14, 1972, Carole King won the most awards, leaving the ceremony with four. Of these four, her album Tapestry won Album of the Year. King’s song, “It’s Too Late,” from the album won Record of the Year, with her “You’ve Got a Friend” song winning Song of the Year.

Christopher Cross

Christopher Cross

Year of Win: 1981

The next time an artist won all three top Grammy categories was almost a decade later, in 1981. American singer-songwriter and guitarist Christopher Cross is best known for his soft rock and adult contemporary music. He rose to fame in the late 1970s and early 1980s with his self-titled debut album, Christopher Cross. The album featured hit songs like “Sailing” and “Ride Like the Wind.” His smooth vocals and sophisticated production style made him stand out at the time. 

Christopher Cross made history at the 23rd Annual Grammy Awards held on February 25, 1981. Besides winning the “Big Three,” Cross is the first artist to win all four major categories in a single night. His Christopher Cross album won Album of the Year, Record of the Year (“Sailing”), Song of the Year (“Sailing”), and Best New Artist. However, despite his early success, his later work did not achieve the same mainstream popularity. Although not a household name today, Christopher Cross remains a respected musician with a dedicated fanbase. 

Eric Clapton

Eric Clapton

Year of Win: 1993

Eric Clapton is a British rock and blues guitarist, singer, and songwriter. Clapton is widely regarded as one of the greatest guitarists of all time, featuring among the top 10 guitarists on the Rolling Stone, Time magazine, and Gibson’s list. Born on March 30, 1945, in Ripley, England, Clapton gained fame in the 1960s with bands like The Yardbirds, John Mayall & the Bluesbreakers, Cream, and Derek and the Dominos before establishing a successful solo career. 

Clapton is known for his songs like “Layla,” “Tears in Heaven,” “Wonderful Tonight,” and “Cocaine,” blending blues, rock, and pop influences. His emotional ballad, “Tears in Heaven,” written after the tragic death of his four-year-old son, won Clayton the Record of the Year and Song of the Year at the 35th Annual Grammy Awards held on February 24, 1993. His album, Unplugged, won the 1993 Album of the Year.

The Chicks

The Chicks

Year of Win: 2007

The Chicks, formerly known as the Dixie Chicks, are no stranger to the Grammys before their iconic “Big Three” win at the 49th Annual Grammy Awards on February 11, 2007. The Chicks are an American country music band known for their harmonious vocals, instrumental talent, and outspoken political views. Formed in 1989 in Texas, the group had its breakthrough in the late 1990s with the addition of lead singer Natalie Maines, who joined founding sisters Martie Maguire and Emily Strayer

The group achieved massive success with albums like Wide Open Spaces (1998) and Fly (1999), which produced multiple hit singles and won several Grammys. However, their 2006 album Taking the Long Way gave them their historical win at the Grammys. Besides winning Album of the Year, their “Not Ready to Make Nice” song won Record of the Year and Song of the Year. They also won two other awards that night to become the year’s biggest winners.  

Adele

Adele

Year of Win: 2012 and 2017

Adele’s success and popularity cut across genres. She is one of the world’s best-selling music artists, with over 120 million records sold worldwide. As of 2025, Adele has won 16 Grammy Awards. The British singer-songwriter is known for her powerful voice, emotional ballads, and timeless music. Her success at the Grammys goes beyond winning the “Big Three” in one night. 

As of the 2025 Grammy Awards, Adele is the only artist to have won the “Big Three” Grammy Awards twice in 2012 and 2017. At the 54th Annual Grammy Awards on February 12, 2012, Adele’s 21 album won Album of the Year. Her song “Rolling in the Deep” won Record of the Year and Song of the Year. History repeated itself five years later at the 59th Annual Grammy Awards on February 12, 2017. Adele’s 25 album won Album of the Year, with her “Hello” song winning Record of the Year and Song of the Year. 

Bruno Mars

Bruno Mars

Year of Win: 2018

Bruno Mars is an American singer, songwriter, and record producer. He’s known for his versatile music style that blends pop, R&B, funk, soul, and reggae. He gained fame for his smooth vocals, energetic performances, and retro-inspired sound. Bruno Mars first rose to prominence in 2010 with hits like “Just the Way You Are,” “Grenade,” and “The Lazy Song.” He joined the exclusive list of the Grammys “Big Three” winners in a single night in 2018. His 24K Magic album won the Album of the Year award, with the songs “24K Magic” and “That’s What I Like” winning Record of the Year and Song of the Year, respectively. 

Billie Eilish

Billie Eilish

Year of Win: 2020

Gen-Z musical icon Billie Eilish is one of her generation’s most successful and popular artists. She’s known for her distinctive voice, dark, introspective lyrics, and genre-blending music. Billie Eilish rose to fame in 2015 when her song “Ocean Eyes” went viral. Billie Eilish grew up in a creative household, with her brother Finneas O’Connell playing a major role in her music production and songwriting.

Her debut album, When We All Fall Asleep, Where Do We Go? (2019) was a critical and commercial success. Billie Eilish made history at the 62nd Annual Grammy Awards by becoming the youngest artist to win the “Big Three” and “Big Four” categories. After Christopher Cross’s “Big Four” win, Billie Eilish is the only other artist to have won all four in a single night. Her When We All Fall Asleep, Where Do We Go? won Album of the Year, with “Bad Guy” winning Record of the Year and Song of the Year. If you enjoyed reading this fact about the Grammy Awards, check out these female musicians who have never won a Grammy.

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