1. Miley Cyrus (2008 vs. 2024)
Jeff Kravitz / FilmMagic, Axelle / FilmMagic
2. Celine Dion (1992 vs. 2024)
Images Press / Getty Images, Cbs Photo Archive / CBS via Getty Images
3. Taylor Swift (2008 vs. 2024)
Kevin Mazur / WireImage, Axelle / FilmMagic
4. Beyoncé (2000 vs. 2024)
Kirby Lee / WireImage, Kevin Mazur / Getty Images for The Recording Academy
5. Tracy Chapman (1989 vs. 2024)
CBS via Getty Images, Kevin Winter / Getty Images for The Recording Academy
6. Lionel Richie (1983 vs. 2024)
Ron Galella, Ltd. / Ron Galella Collection via Getty Images
7. Jay-Z (2004 vs. 2024)
Kmazur / WireImage for NARAS, Valerie Macon / AFP via Getty Images
8. Christina Aguilera (2000 vs. 2024)
Bob Riha Jr / Getty Images, Michael Buckner / Billboard via Getty Images
9. Jordin Sparks (2009 vs. 2024)
Lester Cohen / WireImage, Frazer Harrison / Getty Images
10. Janelle Monáe (2009 vs. 2024)
Frazer Harrison / Getty Images, ROBYN BECK/AFP via Getty Images
11. Joni Mitchell (1970 vs. 2024)
Michael Ochs Archives, Cbs Photo Archive / CBS via Getty Images
12. John Legend (2005 vs. 2024)
Jeff Kravitz / FilmMagic, Inc, ROBYN BECK/AFP via Getty Images
13. Chrissy Teigen (2008 vs. 2024)
Frazer Harrison / Getty Images, Neilson Barnard / Getty Images for The Recording Academy
14. Lana Del Rey (2018 vs. 2024)
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15. Heidi Klum (2010 vs. 2024)
Lester Cohen / WireImage, Gilbert Flores / Billboard via Getty Images
16. Josh Groban (2008 vs. 2024)
Frazer Harrison / Getty Images, Axelle / FilmMagic
17. Jack Antonoff (2013 vs. 2024)
Jeff Vespa / WireImage, Matt Winkelmeyer / Getty Images for The Recording Academy
18. Billy Joel (1981 vs. 2024)
Michael Ochs Archives / Getty Images, Neilson Barnard / Getty Images for The Recording Academy
19. Mariah Carey (1991 vs. 2024)
Images Press / Getty Images, Kevin Winter / Getty Images for The Recording Academy
20. Kelly Clarkson (2004 vs. 2024)
L. Cohen / WireImage, Jeff Kravitz / FilmMagic
21. Fantasia Barrino (2009 vs. 2024)
Gregg Deguire / FilmMagic, Lionel Hahn / Getty Images
22. Kelly Osbourne (2000 vs. 2024)
Vinnie Zuffante / Getty Images, Gilbert Flores / Billboard via Getty Images
23. Paris Jackson (2010 vs. 2024)
Michael Caulfield / WireImage
24. Ed Sheeran (2013 vs. 2024)
Jeff Vespa / WireImage, Lionel Hahn / Getty Images
25. And Brandi Carlile (2016 vs. 2024)
Valerie Macon / AFP via Getty Images, Axelle / FilmMagic
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