| 100% | ADELE | 5 | Singer who released "21" in '11 |
| 70% | JEWEL | 5 | Singer who released her "Picking Up the Pieces" album in 2015 |
| 70% | BILLIEEILISH | 12 | Singer who released "Birds of a Feather" in 2024: 2 wds. |
| 70% | DIDO | 4 | The English singer who released White Flag in 2003 |
| 69% | NELLYFURTADO | 12 | Singer who released "I'm Like a Bird" in 2000: 2 wds. |
| 68% | AVRILLAVIGNE | 12 | Canadian-born singer who released "Sk8er Boi" in 2002: 2 wds. |
| 68% | BLAKE | 5 | James ___, English singer who released the album "Assume Form" in 2019 |
| 68% | INDILA | 6 | French singer who released a song called "Love Story" in 2014 |
| 68% | CAREY | 5 | Mariah ___, singer who released a song called "Love Story" in 2008 |
| 67% | COREYHART | 9 | Canadian-born singer who released "Sunglasses at Night" in 1984: 2 wds. |
| 67% | ARIANA | 6 | ___ Grande, American singer who released the album "Thank U, Next" in 2019 |
| 67% | SOLANGE | 7 | American singer who released the album "When I Get Home" in 2019 |
| 67% | JUSTINBIEBER | 12 | Canadian-born singer who released "Boyfriend" in 2012: 2 wds. |
| 67% | ARIANA | 6 | With 38-Across, singer who released "Sweetener" in 2018 |
| 65% | SYD | 3 | Single named singer who released her debut R&B album "Fin" in February 2017 |
| 63% | NEILYOUNG | 9 | Canadian-born singer who released "Rockin' in the Free World" in 1989: 2 wds. |
| 63% | ALI | 3 | Nadia ___, singer who also released a song called "Love Story" in 2009 |
| 63% | SINATRA | 7 | Singer Frank who starred in the original "Ocean's 11" |
| 63% | ERIC | 4 | Singer Church who released "Heart & Soul" in April |
| 63% | HARRYSTYLES | 11 | "Sign of the Times" pop singer who released a self-titled #1 album in 2017: 2 wds. |
| 63% | CARLYRAEJEPSEN | 14 | "Call Me Maybe" singer who released her sixth studio album, "The Loneliest Time," in 2022 (3 wds.) |
| 62% | JUSTINBIEBER | 12 | Pop singer who released the #1 album "My World 2.0" in 2010, at age 16: 2 wds. |
| 62% | BRITNEYSPEARS | 13 | Pop singer who released the #1 album "… Baby One More Time" in 1999, at age 17: 2 wds. |
| 62% | LADYGAGA | 8 | 15-Across, 9-Down, and 22-Down singer who released the studio album "Mayhem" in 2025 (2 wds.) |
| 61% | BIEBER | 6 | Singer who was 15 in 2009 when his debut EP "My World" was released |
| 61% | CAREY | 5 | Singer Mariah who released her 15th studio album in 2018 |
| 60% | RANDY | 5 | ___ Newman, singer who also released a song called "Love Story (You and Me)" in 1968 |
| 60% | GEORGESTRAIT | 12 | 18-Across and 29-Across singer who released his 30th studio album, "Honky Tonk Time Machine," in 2019 (2 wds.) |
| 59% | SWIFT | 5 | Taylor ___, singer who also released a song called "Love Story" in 2008 and again in 2021 |
| 59% | ANDY | 4 | ___ Williams, singer who also released a song called "(Where Do I Begin?) Love Story" in 1971 |