| 100% | SIA | 3 | Pop singer who released a remix album called "Cheap Thrills" |
| 55% | HARRYSTYLES | 11 | "Sign of the Times" pop singer who released a self-titled #1 album in 2017: 2 wds. |
| 47% | INDILA | 6 | French singer who released a song called "Love Story" in 2014 |
| 47% | CAREY | 5 | Mariah ___, singer who released a song called "Love Story" in 2008 |
| 44% | OSCARDELAHOYA | 13 | Boxing star who released a Grammy-nominated Latin pop album: 4 wds. |
| 44% | JUSTINBIEBER | 12 | Pop singer who released the #1 album "My World 2.0" in 2010, at age 16: 2 wds. |
| 44% | BRITNEYSPEARS | 13 | Pop singer who released the #1 album "… Baby One More Time" in 1999, at age 17: 2 wds. |
| 42% | ALI | 3 | Nadia ___, singer who also released a song called "Love Story" in 2009 |
| 41% | LEA | 3 | Singer/actress ___ Michele who released a Christmas album in 2019 |
| 41% | ARIANAGRANDE | 12 | "Thank U, Next" pop singer who got her seventh #1 hit with a remix of 38-Across: 2 wds. |
| 41% | RANDY | 5 | ___ Newman, singer who also released a song called "Love Story (You and Me)" in 1968 |
| 40% | ANDY | 4 | ___ Williams, singer who also released a song called "(Where Do I Begin?) Love Story" in 1971 |
| 40% | SWIFT | 5 | Taylor ___, singer who also released a song called "Love Story" in 2008 and again in 2021 |
| 40% | OSCARDELAHOYA | 13 | Famed boxer nicknamed "Golden Boy" who released a self-titled Latin Pop album in 2000 - receiving a grammy nomination!: 2 wds. |
| 39% | BRITNEYSPEARS | 13 | Pop singer whom Madonna once called “my talisman” |
| 38% | BILLYPRESTON | 12 | Singer who sang with Nat King Cole on a TV show at 11 and released his first album at 16: 2 wds. |
| 38% | ALISHA | 6 | Dance singer who released the album Nightwalkin' |
| 38% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 37% | JEWEL | 5 | Singer who released her "Picking Up the Pieces" album in 2015 |
| 37% | BILLIEEILISH | 12 | Singer who released "Birds of a Feather" in 2024: 2 wds. |
| 37% | MADONNA | 7 | Pop singer who played Mae in A League of Their Own |
| 37% | NELLYFURTADO | 12 | Singer who released "I'm Like a Bird" in 2000: 2 wds. |
| 37% | SMOKEY | 6 | Singer Robinson who released “Gasms,” his first album of new material in more than a decade, in April, 2023 |
| 36% | REBA | 4 | McEntire who released a gospel album in 2017 |
| 36% | BLAKE | 5 | James ___, English singer who released the album "Assume Form" in 2019 |
| 36% | CARLYRAEJEPSEN | 14 | "Call Me Maybe" singer who released her sixth studio album, "The Loneliest Time," in 2022 (3 wds.) |
| 36% | ARIANA | 6 | ___ Grande, American singer who released the album "Thank U, Next" in 2019 |
| 36% | SOLANGE | 7 | American singer who released the album "When I Get Home" in 2019 |
| 35% | NELLYFURTADO | 12 | Pop singer who had a crossover hit with her 2006 electropop song "Maneater" (2 wds.) |
| 35% | KESHA | 5 | Pop singer who used to use a dollar sign for the third letter of her name |