There have been 65 Album of The Year winners since the Grammy Awards began, with some becoming staples in the ceremony’s legacy. The race for the night’s highest honor is always tight, and the Recording Academy’s choice isn’t always met with favorable reactions. Several times, the results have ended in uproar. In recent years, this has happened mostly when a different artist has won over Beyoncé. Despite being the most-awarded artist in Grammy history, Beyoncé has never received the Album of The Year Grammy. However, the Grammys have honored a handful of other legendary artists with the award.
In 1992, Whitney Houston won Album of The Year for The Bodyguard, making her only the second Black woman to take home the award. In 2010, Taylor Swift became the youngest-ever recipient until Billie Eilish took over that title in 2020. However, some incredible artists like Mariah Carey, Elton John, and Prince never received the award despite making a massive impact on the music industry. Though there have been some poor choices, there have also been times when the Grammys got it right, resulting in some iconic wins. The following are the 10 best, from cultural to musical impact.
10
Taylor Swift: 1989
Swift Won At The 2016 Grammys Ceremony
At the 2016 Grammys, Taylor Swift took home her second Album of The Year trophy. While she was up against some worthy opponents, there was no denying 1989 was the biggest album of the year. It was hard to turn on a pop radio station without hearing one of Swift’s 1989 singles. This was also the era when Swift pulled her music from Spotify, so 1989‘s success came mostly without streaming, though it did remain on Apple Music. After losing Album of The Year for her previous album, Red, Swift made a drastic shift, abandoning country and diving headfirst into pop.
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It was a huge risk, as no other country artist had ever successfully crossed over into pop music. Swift, however, took it and succeeded, as she often does. Before the awards, Kanye West had released his song “Famous,” which ended their brief friendship and continued their decades-long feud. Swift took the opportunity to praise women for their hard work and remind them to never let a man take credit for their success. Swift went on to win the award twice more, becoming the artist with the most Album of The Year wins. Her 1989 win, however, was the most memorable.
9
The Beatles: Sgt. Pepper’s Lonely Hearts Club Band
The Beatles Won At The 1968 Grammys Ceremony
The Beatles became a phenomenon when they hit the music scene, sparking a hysteria coined Beatlemania. It wasn’t until their eighth studio album at the end of the 60s, however, that they’d take home Album of The Year. Sgt. Pepper’s Lonely Hearts Club Band included tracks like “With a Little Help from My Friends” and “Lucy In The Sky With Diamonds.”
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The two tracks would go on to become some of their most well-known hits. The Beatles’ Album of The Year win also marked the first time a rock album took home the coveted award. It was long deserved as they’d already had eleven #1 albums before finally winning Album of The Year.
8
Alanis Morisette: Jagged Little Pill
Morisette Won At The 1996 Grammys Ceremony
Before Taylor Swift and Olivia Rodrigo made waves with their angry breakup songs, Alanis Morrisette took the world by storm with her celebration of female rage titled Jagged Little Pill. The album included her best-known song to date, “You Oughta Know,” which both Swift and Rodrigo sang with her on their respective tours. Women have been shamed for their anger throughout history, but with Jagged Little Pill, Morisette encouraged women to embrace their rage.
The album would inspire a Broadway musical in 2019 and would become the blueprint for other singer-songwriters looking to express their bitter emotions through music. This is now a more common theme in modern music, but it may not be as prevalent were it not for Jagged Little Pill. This cultural impact no doubt makes this a memorable Album of The Year win, especially seeing how it has since paved the way for other artists like Morrisette to achieve a similar feat.
7
Bob Dylan: Time Out Of Mind
Dylan Won At The 1998 Grammys Ceremony
Bob Dylan was a trailblazer in folk music. He was also fearless in terms of experimenting with new sounds, no matter how much it angered his fans. A Complete Unknown takes audiences through Dylan’s first time performing his rock-inspired album, which didn’t go over well with the crowd.
Despite his legacy, it wasn’t until 1998 that Dylan won his first Album of The Year for one of his solo albums. Dylan’s win was long overdue and well-deserved, as Time Out of Mind had several legendary tracks, including “Make You Feel My Love.” The song would go on to be covered several times, most notably by Adele for her 2008 album, 19.
6
Carole King: Tapestry
King Won At The 1972 Grammys Ceremony
Carole King is one of the most prolific singer-songwriters in music history, acting as an inspiration for the ones who would come after her. Tapestry was a profound album, with tracks like “It’s Too Late,” which took home Record of The Year, and “You’ve Got A Friend,” which took home Song of The Year. Her Song of The Year win even made her the first woman to win the award.
In 2014, Tapestry‘s track “Beautiful” inspired the Broadway musical about her life, and she’d return to the Grammys that year to sing the song with Sara Bareilles. King was only the third woman to win Album of The Year, signifying just how impactful the album was and what her legacy would be. 26 years after her win, Tapestry was inducted into the Grammy Hall of Fame.
5
Stevie Wonder: Innervisions
Wonder Won At The 1974 Grammys Ceremony
In 1974, Stevie Wonder won Album of The Year with “Innervisions” and became the first Black artist ever to take the award home. The crowd erupted in applause as Cher presented Wonder with the golden trophy. Wonder gave a powerful speech, hoping his music would continue to influence a better future.
The singer would win the award two more times, becoming one of three artists with the most wins until Taylor Swift broke the record in 2024. However, his first win will always be the most iconic, as it broke down barriers for Black artists who would come after him. This easily makes Wonder’s win one of the best in Grammys history.
4
Frank Sinatra: A Man And His Music
Sinatra Won At The 1967 Grammys Ceremony
Frank Sinatra was the second artist to ever win Album of The Year back in 1960. However, he broke a special record in 1967 with his win for A Man and His Music. Not only did the album make Sinatra the first artist to win the award three times, but it was also the first time an artist consecutively won Album of The Year. The Chairman of the Board won in 1966 for his album September of My Years before winning again at the following ceremony.
To this day, Sinatra and Stevie Wonder are the only artists to ever win Album of The Year two years in a row. A Man and His Music was made up of mostly re-recordings of Sinatra’s previously released songs and acted as a celebration of his revolutionary career. The previously released songs made the win more impressive, as Sinatra didn’t even have to release new music for the Academy to celebrate his work.
3
Lauryn Hill: The Miseducation Of Lauryn Hill
Hill Won At The 1999 Grammys Ceremony
Lauryn Hill was the third Black woman to win Album of The Year at the Grammys. Part of what made the moment so special was that Whitney Houston presented the award to her, encouraging the crowd to cheer for Hill’s big win. The Miseducation of Lauryn Hill was Hill’s first and only solo album, making her win an even bigger accomplishment, especially because she was up against some big names.
Hill beat out Madonna, Sheryl Crow, and Shania Twain with her win, so it was quite profound. In her acceptance speech, she highlighted how special it was to win for a hip-hop album as Houston excitedly cheered in the background. The Miseducation of Lauryn Hill was one of the most acclaimed albums of 1998, and remains highly praised to this day.
2
Fleetwood Mac: Rumours
Fleetwood Mac Won At The 1978 Grammys Ceremony
Fleetwood Mac’s album Rumours is #7 on Rolling Stone‘s 500 Greatest Albums of All Time list. The publication referred to it as the best breakup album ever released, and Grammy voters seemed to agree it was excellent. The album is flooded with iconic breakup tracks, with the 2004 remastered version including the legendary Fleetwood Mac track “Silver Springs.”
Rumours remains one of the best-selling albums of all time, with all four of its released singles charting in the top 10 of Billboard’s Hot 100. The album has incredible lore with all the behind-the-scenes breakup drama, which only adds to its legacy. However, even without the stories, the music stands on its own and was well-deserving of the Grammys’ highest honor of the night. Only one other Album of The Year win manages to best this iconic album.
1
Michael Jackson: Thriller
Jackson Won At The 1984 Grammys Ceremony
One Album of The Year winner stands out among the 64 others, and that’s Michael Jackson’s Thriller. The album remains the best-selling of all time, and was a pivotal moment in Jackson’s career. Similar to Taylor Swift’s pivot to pop music, Jackson was frustrated when Off the Wall wasn’t nominated for Album of The Year. The only nominations he received were for his single “Don’t Stop Til You Get Enough.” Jackson was also frustrated about being boxed into the R&B genre, so he set out to become the King of Pop. Needless to say, he succeeded beyond his wildest dreams.
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Thriller‘s win represented all the hard work Jackson had put into his career. The singer accepted the award in his bedazzled jacket and iconic sparkly glove, taking the stage with legendary producer Quincy Jones. Thriller was the blueprint for all the pop albums that came after it, and Michael Jackson is still the blueprint for modern pop stars. While the Grammys will continue to hand out their Album of The Year trophy to several more excited recipients, it will be hard to beat the legacy of Michael Jackson’s Thriller.
