Olivia Rodrigo could make her first three studio albums Album of the Year nominees if You Seem Pretty Sad for a Girl So in Love earns a Grammy nod. LAS VEGAS, NEVADA – APRIL 03: Olivia Rodrigo accepts the Best Pop Vocal Album award for ‘Sour’ onstage during the 64th Annual GRAMMY Awards at MGM Grand Garden Arena on April 03, 2022 in Las Vegas, Nevada. (Photo by Rich Fury/Getty Images for The Recording Academy)
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Olivia Rodrigo has never released an album that Grammy voters didn’t consider one of the best of the year. That statement may very well remain true when nominations for the 2027 ceremony are announced next month. Rodrigo’s third studio set You Seem Pretty Sad for a Girl So in Love is a major commercial and critical success, and another Album of the Year nod would make her three-for-three in the category.
Plenty of superstars eventually collect several nominations for the Grammys’ biggest prize, but almost nobody has started a career by sending every one of their first three albums into the race.
Olivia Rodrigo Is Already Two-For-Two
Rodrigo first found herself in the race for Album of the Year with her debut, Sour, which was up for the honor at the 2022 Grammys. The collection lost the top prize to Jon Batiste’s We Are – a major shock at the time – though Rodrigo did enjoy an incredible evening. She won Best New Artist, Best Pop Vocal Album and Best Pop Solo Performance for “Drivers License.”
Two years later, Guts brought her right back to the Album of the Year category, but she lost the honor again. At the 2024 ceremony, Taylor Swift’s Midnights prevailed, making her the first artist to score the hardware four times.
Olivia Rodrigo’s New Album Was Another Critical and Commercial Win
You Seem Pretty Sad for a Girl So in Love looks well positioned to preserve Rodrigo’s perfect nomination streak. The collection debuted at No. 1 on the Billboard 200 with the largest opening of the superstar’s career, and reviews have been overwhelmingly positive. A nomination is never guaranteed for anyone or any project, especially in a field with only eight available spaces, but Rodrigo is set to enter the Grammy race with essentially everything that typically helps an Album of the Year contender. If she makes the cut, her entire studio discography will consist of Album of the Year nominees.
Ye Pulled Off the Same Grammy Streak
Ye – formerly known as Kanye West – can be thought of as perhaps the clearest precedent to what Rodrigo is hoping to achieve. His debut, The College Dropout, competed for Album of the Year in 2005. Follow-up Late Registration returned him to the field one year later, and his third studio effort Graduation completed the streak at the 2008 ceremony.
LOS ANGELES, CA – FEBRUARY 08: Singer Kanye West poses with his Best Rap Song, Best Rap Solo Performance and Best Rap Album awards in the press room at the 48th Annual Grammy Awards at the Staples Center on February 8, 2006 in Los Angeles, California. (Photo by Kevin Winter/Getty Images)
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West lost all three times, but becoming an Album of the Year nominee with each of his first three studio albums set an extraordinarily difficult standard for anyone else to match. Even many artists who eventually became Grammy fixtures failed to begin their careers so successfully.
Taylor Swift’s self-titled debut, for example, never earned an Album of the Year nod. Adele’s 19 missed the category as well. Beyoncé has become one of the most decorated musicians in Grammy history, but her solo debut Dangerously in Love was not nominated for the top prize.
Billie Eilish Is Olivia Rodrigo’s Closest Modern Comparison
Billie Eilish accomplished the same feat that Rodrigo may manage, and she’s done so very recently. When We All Fall Asleep, Where Do We Go? was nominated for Album of the Year in 2020 and won, making her the youngest lead act to score the trophy. Happier Than Ever returned Eilish to the vertical in 2022, while Hit Me Hard and Soft made her three-for-three in 2025.
LOS ANGELES, CALIFORNIA – JANUARY 26: Billie Eilish poses with her awards in the press room during the 62nd Annual GRAMMY Awards at STAPLES Center on January 26, 2020 in Los Angeles, California. (Photo by Alberto E. Rodriguez/Getty Images for The Recording Academy)
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Eilish is the only woman who owns this winning run of nominations, when looking specifically at albums they lead as an artist. In only a few weeks, Rodrigo could join her.
Lady Gaga Makes the Historic Record Slightly Complicated
Lady Gaga also deserves a place in this conversation, although her discography makes the record a little messier. The pop icon’s debut set The Fame competed for Album of the Year in 2010, The Fame Monster followed in 2011 and Born This Way earned another nomination in 2012. Grammy voters embraced Gaga’s first three major projects in consecutive years.
The complication is that The Fame Monster is generally classified as an EP in the United States – and in other territories it’s known as an expanded reissue – rather than Gaga’s second traditional studio album. Looking specifically at full-length albums, Gaga’s first three titles are The Fame, Born This Way and Artpop, and the last of that trio was not nominated.
LOS ANGELES, CALIFORNIA – FEBRUARY 01: Lady Gaga, winner of the Best Pop Vocal Album for “MAYHEM” and Best Dance Pop Recording for “Abracadabra”, poses in the press room during the 68th GRAMMY Awards at Crypto.com Arena on February 01, 2026 in Los Angeles, California. (Photo by Leon Bennett/Getty Images for The Recording Academy)
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Olivia Rodrigo Could Do Something No Other Artist Has
Rodrigo has a shot at not only entering this club, but managing something that Ye, Eilish and Gaga have not. Ye lost Album of the Year with Graduation. Gaga lost with Born This Way. Eilish lost with Hit Me Hard and Soft.
Rodrigo has already failed to claim Album of the Year twice. If You Seem Pretty Sad for a Girl So in Love reaches the field and ultimately takes the trophy, she would become the first member of this tiny group to win specifically with album No. 3.
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