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Grammys flashback: See Billie Eilish, Madonna, Whitney Houston make awards history

Kim Willis,Edward Segarra
Jan. 29, 2026, 3:36 p.m. ET
Grammy nominees Charley Pride, left, with his wife Rozene (center left), and Helen Reddy, with her husband Jeff Wald, talk during a pre-Grammy cocktail party on March 3, 1973. Pride went on to win the award for best male country vocal performance at the 15th annual Grammy Awards.
Grammy nominees Charley Pride, left, with his wife Rozene (center left), and Helen Reddy, with her husband Jeff Wald, talk during a pre-Grammy cocktail party on March 3, 1973. Pride went on to win the award for best male country vocal performance at the 15th annual Grammy Awards.
Jack Corn/The Tennessean
U2 poses with one of their Grammy awards at the 30th annual Grammy Awards on March 2, 1988. The band won album of the year and best rock vocal performance by a duo or group for their No. 1 album "The Joshua Tree," which boasted the No. 1 hit "I Still Haven't Found What Looking For."
U2 poses with one of their Grammy awards at the 30th annual Grammy Awards on March 2, 1988. The band won album of the year and best rock vocal performance by a duo or group for their No. 1 album "The Joshua Tree," which boasted the No. 1 hit "I Still Haven't Found What Looking For."
Barbara Kinney, USA TODAY
Michael Jackson, right, kisses sister Janet Jackson on the cheek after she presented him with the Grammy Legend Award at the 35th annual Grammy Awards on Feb. 24, 1993. Jackson was also nominated for a trio of awards at the ceremony: best male pop vocal performance, best male R&B vocal performance and best R&B song.
Michael Jackson, right, kisses sister Janet Jackson on the cheek after she presented him with the Grammy Legend Award at the 35th annual Grammy Awards on Feb. 24, 1993. Jackson was also nominated for a trio of awards at the ceremony: best male pop vocal performance, best male R&B vocal performance and best R&B song.
SCOTT FLYNN, AFP/Getty Images
Paula Cole reacts to her Grammy win for best new artist at the 40th annual Grammy Awards on Feb. 25, 1998. Cole was also nominated in six other categories at the ceremony: record, album and song of the year, best female pop vocal performance, best pop album and producer of the year non-classical.
Paula Cole reacts to her Grammy win for best new artist at the 40th annual Grammy Awards on Feb. 25, 1998. Cole was also nominated in six other categories at the ceremony: record, album and song of the year, best female pop vocal performance, best pop album and producer of the year non-classical.
EILEEN BLASS, USA TODAY
Chris Rock throws his Grammy for best spoken comedy album in the air at the 40th annual Grammy Awards on Feb. 25, 1998. Rock received the award for "Roll With the New."
Chris Rock throws his Grammy for best spoken comedy album in the air at the 40th annual Grammy Awards on Feb. 25, 1998. Rock received the award for "Roll With the New."
MATT CAMPBELL, AFP
Olympic figure Tara Lipinski, center, presents the award for best pop album alongside members of Boyz II Men at the 40th annual Grammy Awards on Feb. 25, 1998.
Olympic figure Tara Lipinski, center, presents the award for best pop album alongside members of Boyz II Men at the 40th annual Grammy Awards on Feb. 25, 1998.
EILEEN BLASS, USA TODAY
Mike Myers, right, kneels before Erykah Badu as he presents her with the Grammy for best female R&B vocal performance at the 40th annual Grammy Awards on Feb. 25, 1998. Badu also nabbed the award for best R&B album for her triple-platinum debut album "Baduizm."
Mike Myers, right, kneels before Erykah Badu as he presents her with the Grammy for best female R&B vocal performance at the 40th annual Grammy Awards on Feb. 25, 1998. Badu also nabbed the award for best R&B album for her triple-platinum debut album "Baduizm."
EILEEN BLASS, USA TODAY
Brandy and Monica embrace after winning a Grammy for best R&B vocal performance by a duo or group at the 41st annual Grammy Awards on Feb. 24, 1999. The singers received the award for their collaboration "The Boy Is Mine," which peaked at No. 1 on the Billboard Hot 100.
Brandy and Monica embrace after winning a Grammy for best R&B vocal performance by a duo or group at the 41st annual Grammy Awards on Feb. 24, 1999. The singers received the award for their collaboration "The Boy Is Mine," which peaked at No. 1 on the Billboard Hot 100.
Robert Hanashiro, USA TODAY
Madonna gets a kiss from Jerry Seinfeld after winning at the 41st annual Grammy Awards on Feb. 24, 1999. Madonna scored a trio of awards at the ceremony for her multiplatinum "Ray of Light": best dance recording, best pop album and best short form music video.
Madonna gets a kiss from Jerry Seinfeld after winning at the 41st annual Grammy Awards on Feb. 24, 1999. Madonna scored a trio of awards at the ceremony for her multiplatinum "Ray of Light": best dance recording, best pop album and best short form music video.
Robert Hanashiro, USA TODAY
Whitney Houston performs at Clive Davis 2011 Pre-Grammy Gala at the Beverly Hilton on Feb. 12, 2011, a year before her death. Over the course of her illustrious career, Houston was nominated for 25 Grammys and won six.
Whitney Houston performs at Clive Davis 2011 Pre-Grammy Gala at the Beverly Hilton on Feb. 12, 2011, a year before her death. Over the course of her illustrious career, Houston was nominated for 25 Grammys and won six.
MARK RALSTON, AFP/Getty Images
Billie Eilish was the first artist since Christopher Cross to sweep the "big four" Grammy categories (album of the year, record of the year, song of the year and best new artist), a feat she accomplished on Jan. 26, 2020.
Billie Eilish was the first artist since Christopher Cross to sweep the "big four" Grammy categories (album of the year, record of the year, song of the year and best new artist), a feat she accomplished on Jan. 26, 2020.
FREDERIC J. BROWN, AFP Via Getty Images
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