| 100% | DUALIPA | 7 | Pop singer whose "Levitating" was Billboard's best-performing song of 2021: 2 wds. |
| 60% | GLASSANIMALS | 12 | Indie rock band whose "Heat Waves" was Billboard's best-performing song of 2022: 2 wds. |
| 53% | LILNASX | 7 | Rapper whose "Old Town Road" was Billboard's best-performing song of 2019: 3 wds. |
| 51% | MICHAELJACKSON | 14 | Pop singer whose hologram performed at the Billboard Music Awards in 2014: 2 wds. |
| 51% | BRITNEYSPEARS | 13 | Pop singer whose name is an anagram of the word "Presbyterians": 2 wds. |
| 50% | OLIVIARODRIGO | 13 | "Good 4 U" singer who was Billboard's 2021 Woman of the Year: 2 wds. |
| 49% | BRANDICARLILE | 13 | Singer whose 2021 hit song "Right on Time" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 47% | ALJARREAU | 9 | Singer whose "Moonlighting" was the theme song for the TV show of the same name: 2 wds. |
| 47% | TIKTOK | 6 | Kesha song that was Billboard's top pop song of 2010: 2 wds. |
| 47% | BADDAY | 6 | Daniel Powter song that was Billboard's top pop song of 2006: 2 wds. |
| 47% | UPTOWNFUNK | 10 | Mark Ronson song that was Billboard's top pop song of 2015: 2 wds. |
| 46% | HARRYSTYLES | 11 | Singer whose "As It Was" won the MTV Video Music Award for Best Pop Video in 2022: 2 wds. |
| 46% | JUSTINBIEBER | 12 | "Love Yourself" pop singer who was Billboard's Top Male Artist of 2016: 2 wds. |
| 45% | BENSONBOONE | 11 | Singer whose "Beautiful Things" was the best-selling global single of 2024: 2 wds. |
| 45% | ANDREABOCELLI | 13 | Italian classical singer whose album "Cinema" was nominated for Best Traditional Pop Vocal Album in the 2017 Grammy Awards : 2 wds. |
| 45% | KENNYCHESNEY | 12 | "The Good Stuff" singer whose songs have spent 72 weeks at #1 on Billboard's Hot Country chart: 2 wds. |
| 44% | LILNASX | 7 | Singer whose 2021 hit song "Montero (Call Me by Your Name)" is nominated for three Grammy Awards, including Record of the Year (3 wds.) |
| 44% | THRIFTSHOP | 10 | Macklemore & Ryan Lewis song that was Billboard's top pop song of 2013: 2 wds. |
| 43% | PAULACOLE | 9 | Singer whose "I Don't Want to Wait" was the theme song for "Dawson's Creek": 2 wds. |
| 43% | HARRYSTYLES | 11 | Singer whose "As It Was" was the best-selling global single of 2022: 2 wds. |
| 42% | OLIVIARODRIGO | 13 | Singer whose 2021 hit single "Drivers License" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 42% | LUKECOMBS | 9 | Country singer whose cover of 27-Across's "Fast Car" was a #2 hit in 2023: 2 wds. |
| 42% | CELINEDION | 10 | Singer whose 1996 album "Falling into You" won Grammy Awards for Album of the Year and Best Pop Album (2 wds.) |
| 42% | JOHNDENVER | 10 | "Annie's Song" singer whose surname is Colorado's capital: 2 wds. |
| 42% | ALGREEN | 7 | Singer whose name is an anagram of the word "general": 2 wds. |
| 42% | DOJACAT | 7 | Singer whose 2021 hit single "Kiss Me More" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 42% | PETESEEGER | 10 | Folk singer whose anti-Vietnam War song on 15-/51-Across's show was censored by CBS: 2 wds. |
| 42% | TAYLORSWIFT | 11 | Seven-time Grammy-winning country and pop singer who was EW's 2010 Entertainer of the Year: 2 wds. |
| 42% | LITTLEEVA | 9 | Pop singer whose version of "The Loco-Motion" inspired a dance craze in the 1960s: 2 wds. |
| 42% | TOBYKEITH | 9 | "Red Solo Cup" singer whose songs have spent 53 weeks at #1 on Billboard's Hot Country chart: 2 wds. |