| 100% | MICHAELJACKSON | 14 | Pop singer whose hologram performed at the Billboard Music Awards in 2014: 2 wds. |
| 51% | MARIACALLAS | 11 | Opera singer whose hologram performed at Lincoln Center in 2018: 2 wds. |
| 50% | TAYLORSWIFT | 11 | Singer whose "Anti-Hero" won the MTV Video Music Award for Best Pop Video in 2023: 2 wds. |
| 47% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 46% | JENNIFERLOPEZ | 13 | "Waiting for Tonight" singer who received the Billboard Icon Award in 2014: 2 wds. |
| 46% | JUSTINBIEBER | 12 | Singer whose "Peaches" won the MTV Video Music Award for Best Pop Video in 2021: 2 wds. |
| 45% | HARRYSTYLES | 11 | Singer whose "As It Was" won the MTV Video Music Award for Best Pop Video in 2022: 2 wds. |
| 44% | TUPACSHAKUR | 11 | Rapper whose hologram performed at Coachella in 2012: 2 wds. |
| 44% | ANDREABOCELLI | 13 | Italian classical singer whose album "Cinema" was nominated for Best Traditional Pop Vocal Album in the 2017 Grammy Awards : 2 wds. |
| 43% | KNOWINGYOU | 10 | Top 10 single that 30-Across performed at the Academy of Country Music Awards ceremony in 2021 (2 wds.) |
| 41% | LITTLEEVA | 9 | Pop singer whose version of "The Loco-Motion" inspired a dance craze in the 1960s: 2 wds. |
| 40% | DUALIPA | 7 | Pop singer whose "Levitating" was Billboard's best-performing song of 2021: 2 wds. |
| 40% | CHRISSTAPLETON | 14 | Country singer whose album "Traveller" topped the Billboard 200 in 2015: 2 wds. |
| 40% | MARIAHCAREY | 11 | "Emotions" singer who received the Billboard Icon Award in 2019: 2 wds. |
| 39% | JUSTINBIEBER | 12 | Pop singer who released the #1 album "My World 2.0" in 2010, at age 16: 2 wds. |
| 39% | BRITNEYSPEARS | 13 | Pop singer who released the #1 album "… Baby One More Time" in 1999, at age 17: 2 wds. |
| 39% | KYLIEMINOGUE | 12 | "Padam Padam" singer who received the Billboard Women in Music Icon Award in 2024: 2 wds. |
| 39% | JOSEFELICIANO | 13 | "Feliz Navidad" singer who received the Billboard Latin Music Lifetime Achievement Award in 1996: 2 wds. |
| 39% | NEILDIAMOND | 11 | "Sweet Caroline" singer who received the Billboard Icon Award in 2011: 2 wds. |
| 39% | MARIAHCAREY | 11 | Singer whose song "We Belong Together" peaked at number one on the Billboard Hot 100 chart in 2005: 2 wds. |
| 39% | MEGHANTRAINOR | 13 | Singer whose debut single "All About That Bass" reached #1 on the Billboard Hot 100 in 2014: 2 wds. |
| 38% | LUKECOMBS | 9 | Singer whose 2023 hit "Fast Car" spent 8 weeks at #2 on the Billboard Hot 100 without hitting #1: 2 wds. |
| 38% | SARABAREILLES | 13 | "Love Song" singer/pianist who performed a duet with 18-Across at the Grammy Awards in 2014 (2 wds.) |
| 38% | DEBBIEHARRY | 11 | Lead singer of Blondie who received the first Billboard Women in Music Icon Award, in 2008: 2 wds. |
| 38% | EDSHEERAN | 9 | Singer whose 2015 hit "Thinking Out Loud" spent 8 weeks at #2 on the Billboard Hot 100 without hitting #1: 2 wds. |
| 38% | RICKYMARTIN | 11 | Singer whose song "Livin' La Vida Loca" peaked at number one on the Billboard Hot 100 chart in 1999: 2 wds. |
| 38% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 38% | ADELEADKINS | 11 | British singer whose third studio album fetched her the Album of the Year in the 2017 Grammy Awards : 2 wds. |
| 38% | NICKIMINAJ | 10 | Rapper whose song "Anaconda" peaked at #2 on the Billboard Hot 100 in August 2014: 2 wds. |
| 38% | MEGHANTRAINOR | 13 | Singer whose "All About That Bass" spent 25 weeks in the Billboard Top 10 in 2014 and 2015: 2 wds. |