If You Seem Pretty Sad for a Girl So in Love earns an Album of the Year Grammy nod, Olivia Rodrigo will join Lady Gaga, Ye and Billie Eilish in a historic feat. LAS VEGAS, NEVADA – APRIL 03: Olivia Rodrigo, winner of the Best New Artist and Best Pop Solo Performance Award for ‘Drivers License’ poses in the winners photo room during the 64th Annual GRAMMY Awards at MGM Grand Garden Arena on April 03, 2022 in Las Vegas, Nevada. (Photo by Kevin Mazur/Getty Images for The Recording Academy)
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Olivia Rodrigo has so far managed a perfect streak at the Grammys when it comes to what is usually considered the top category at the annual ceremony. Both of her first two albums, Sour and Guts, were nominated for multiple awards, including Album of the Year, the prize given to the project deemed the “best” – though what exactly that means is left purposefully vague – by Recording Academy voters.
Neither collection ended up winning that honor – Sour lost to Jon Batiste’s We Are and Guts was bested by Taylor Swift’s record-setting Midnights – though Rodrigo has taken home several trophies throughout her short career. The pop superstar recently released another blockbuster with You Seem Pretty Sad for a Girl So in Love, her third full-length. The project easily conquered rankings all around the world, and will likely end 2026 as one of the top-performing albums and a critical favorite.
You Seem Pretty Sad for a Girl So in Love seems like it will earn Rodrigo several more Grammy nominations, and perhaps even another Album of the Year nod. If it does end up competing for the prestigious honor, that streak will remain golden, and she will join a very small group of artists whose first three albums were all nominated for the top prize.
Olivia Rodrigo Could Join Lady Gaga and Billie Eilish
STOCKHOLM, SWEDEN – APRIL 23: Billie Eilish performs at Avicii Arena on April 23, 2025 in Stockholm, Sweden. (Photo by Samir Hussein/WireImage for Live Nation)
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Rodrigo would not be the first musician to see each of her first three albums compete for Album of the Year – if You Seem Pretty Sad for a Girl So in Love does wind up as one of the eight nominated titles. Kanye West managed the feat nearly 20 years ago with The College Dropout, Late Registration and Graduation.
Lady Gaga followed only a few years later with The Fame, The Fame Monster and Born This Way. Impressively, those projects were nominated in three consecutive years, as the singer vied for Album of the Year in 2010, 2011 and 2012.
Billie Eilish also earned the distinction with her first three full-lengths, When We All Fall Asleep, Where Do We Go?, Happier Than Ever and Hit Me Hard and Soft. Amazingly, among that trio of artists, only Eilish has won Album of the Year – and just once. She claimed the trophy with her debut collection, When We All Fall Asleep, Where Do We Go?, when she was still a teenager.
LAS VEGAS, NEVADA – JULY 16: (Exclusive Coverage) Lady Gaga performs during the kick off of The MAYHEM Ball tour at T-Mobile Arena on July 16, 2025 in Las Vegas, Nevada. (Photo by Kevin Mazur/Getty Images for Live Nation)
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Rodrigo Is Already a 14-Time Grammy Nominee
Rodrigo has already racked up a total of 14 Grammy nominations – an incredible total for a musician who is only 23 years old. She first competed at the ceremony in 2022, when she was nominated for seven prizes. Rodrigo won three of them, including Best New Artist, the only Grammy an artist may be nominated for just once. That year, Sour took home Best Pop Vocal Album, while “Drivers License,” its lead single and the singer’s first global smash, won Best Pop Solo Performance.
Two years later, Rodrigo returned with six more nominations tied to her sophomore set Guts. That collection brought her back to the Album of the Year vertical, but she walked away empty-handed.
The singer was most recently nominated in 2025 for “Can’t Catch Me Now” in the Best Song Written for Visual Media category. Rodrigo wrote and recorded the track for The Hunger Games: The Ballad of Songbirds & Snakes, but .
A Third Album of the Year Nomination Seems Possible
You Seem Pretty Sad for a Girl So in Love immediately become another major commercial smash for Rodrigo around the world, just as Sour and Guts did upon their arrivals. A huge sales debut and applause from fans and music critics does not guarantee Grammy recognition, but they both help. The singer established herself as a favorite among Recording Academy voters from the moment she launched her solo music career, and while she doesn’t always come out on top, the fact that she regularly returns – and in the most competitive fields – is a sign that she’s not one to count out. Will her third time in the category make her a winner?
Eligibility for the 2027 Grammy Awards began on August 31, 2025 and closes on August 28, 2026. The ceremony will air live on February 7, 2027.