| 100% | BRITNEYSPEARS | 13 | Pop singer who released the #1 album "… Baby One More Time" in 1999, at age 17: 2 wds. |
| 62% | JUSTINBIEBER | 12 | Pop singer who released the #1 album "My World 2.0" in 2010, at age 16: 2 wds. |
| 53% | STEVIEWONDER | 12 | R&B singer who released the #1 album "Recorded Live: The 12 Year Old Genius" in 1963, at age 13: 2 wds. |
| 50% | BRITNEYSPEARS | 13 | "Baby One More Time" pop singer who cameoed in "The Simpsons" episode, "The Mansion Family" as herself: 2 wds. |
| 50% | HARRYSTYLES | 11 | "Sign of the Times" pop singer who released a self-titled #1 album in 2017: 2 wds. |
| 45% | BRITNEYSPEARS | 13 | Musician whose first single "... Baby one more time" topped the charts in 1998 when she was just 17 years old: 2 wds. |
| 39% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 38% | ALESSIACARA | 11 | "Stay" singer who won the Pop Album of the Year Juno in 2017: 2 wds. |
| 37% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 37% | CARLYRAEJEPSEN | 14 | "Call Me Maybe" singer who released her sixth studio album, "The Loneliest Time," in 2022 (3 wds.) |
| 36% | GEORGESTRAIT | 12 | 18-Across and 29-Across singer who released his 30th studio album, "Honky Tonk Time Machine," in 2019 (2 wds.) |
| 36% | COREYHART | 9 | Canadian-born singer who released "Sunglasses at Night" in 1984: 2 wds. |
| 36% | FIONAAPPLE | 10 | 18-Across, 25-Across, and 38-Across singer who released her fifth studio album "Fetch the Boltcutters" in 2020 (2 wds.) |
| 35% | NEILYOUNG | 9 | Canadian-born singer who released "Rockin' in the Free World" in 1989: 2 wds. |
| 35% | GERIHALLIWELL | 13 | Singer who had four #1 hits in the UK from 1999 to 2001, including "It's Raining Men": 2 wds. |
| 35% | EDSHEERAN | 9 | "Shape of You" singer who won two awards, including Best Pop Vocal Album, at the 2018 Grammy Awards (2 wds.) |
| 35% | TAYLORSWIFT | 11 | "Cardigan" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 35% | LADYGAGA | 8 | "Shallow" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 35% | MICHAELJACKSON | 14 | Pop singer whose hologram performed at the Billboard Music Awards in 2014: 2 wds. |
| 35% | LAURYNHILL | 10 | "Everything Is Everything" singer who received the Grammys for both Album of the Year and Best New Artist in 1999: 2 wds. |
| 34% | ELVISCOSTELLO | 13 | "Look Now" singer who won the Best Traditional Pop Vocal Album Grammy Award in 2020 (2 wds.) |
| 34% | THEWEEKND | 9 | "Starboy" pop singer who had 18 songs on the Billboard Hot 100 during a week in 2016: 2 wds. |
| 34% | EDSHEERAN | 9 | "Shape of You" pop singer who had 13 songs on the Hot 100 during a week in 2017: 2 wds. |
| 34% | EMMYLOUHARRIS | 13 | "Blue Kentucky Girl" singer who's one of the three women on the 1987 album "Trio": 2 wds. |
| 34% | DOLLYPARTON | 11 | "9 to 5" singer who's one of the three women on the 1987 album "Trio": 2 wds. |
| 34% | DOLLYPARTON | 11 | "Jolene" singer who was inducted into the Country Music Hall of Fame in 1999: 2 wds. |
| 33% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 33% | SPEARS | 6 | The surname of Baby One More Time singer |
| 33% | TORIKELLY | 9 | "Nobody Love" singer who first started posting videos on YouTube at the age of 14: 2 wds. |
| 33% | BILLIEEILISH | 12 | "Bad Guy" singer who was one of PETA's Most Beautiful Vegan Celebrities in 2021: 2 wds. |