| 100% | NANCYSINATRA | 12 | "Somethin' Stupid" singer who also sang 1965's "These Boots Are Made for Walkin'": 2 wds. |
| 66% | NANCYSINATRA | 12 | "These Boots Were Made for Walkin'" singer who sang on an episode of "The Sopranos": 2 wds. |
| 50% | NANCYSINATRA | 12 | Performer with the 1966 hit "These Boots Are Made for Walkin'": 2 wds. |
| 45% | SINATRA | 7 | "These Boots Are Made for Walkin'" singer Nancy |
| 41% | PATSYCLINE | 10 | "Crazy" singer who also sang 1957's "Walkin' After Midnight": 2 wds. |
| 38% | BASS | 4 | Prominent instrument in "These Boots Are Made for Walkin'" |
| 37% | BILLIEEILISH | 12 | Singer-songwriter who sings "What Was I Made For?" on "Barbie: The Album" (2 wds.) |
| 36% | THESE | 5 | Nancy Sinatra's "___ Boots Are Made for Walkin'" |
| 36% | THESE | 5 | "___ Boots Are Made for Walkin'" |
| 36% | THESE | 5 | "___ Boots Are Made for Walkin'" (1966 hit) |
| 35% | THESE | 5 | "___ Boots Are Made for Walkin'" (Nancy Sinatra hit) |
| 35% | ANNIELENNOX | 11 | "Sweet Dreams (Are Made of This)" singer who was voted into the Songwriters Hall of Fame in 2020: 2 wds. |
| 35% | THESE | 5 | "___ Boots Are Made for Walkin'" (1966 Nancy Sinatra hit) |
| 35% | THESE | 5 | "____ Boots Are Made for Walkin'" (1966 Nancy Sinatra hit) |
| 35% | LUCYDACUS | 9 | "Kissing Lessons" singer who is also a member of 16-Across: 2 wds. |
| 35% | KEITHURBAN | 10 | Country singer who was an "American Idol" judge for four seasons: 2 wds. |
| 34% | SHERYLCROW | 10 | "All I Wanna Do" singer who sang backup for Michael Jackson and Stevie Wonder: 2 wds. |
| 34% | JOHNLEGEND | 10 | "All of Me" singer who sang backup for Alicia Keys and Kanye West: 2 wds. |
| 33% | JENNIFERLOPEZ | 13 | Singer who was nominated for a Grammy for Best Dance Recording in 2000 but lost to Cher: 2 wds. |
| 33% | NOAHKAHAN | 9 | "Hurt Somebody" rock singer who was nominated for Best New Artist at the 2024 Grammys: 2 wds. |
| 33% | HARRYBELAFONTE | 14 | "Day-O" singer who was blacklisted for his leftist views in the Joseph McCarthy period: 2 wds. |
| 33% | CLAYAIKEN | 9 | "This Is the Night" singer who is running for Congress in North Carolina: 2 wds. |
| 33% | TAYLORSWIFT | 11 | Singer who was nominated for a Grammy for Best New Artist in 2008 but lost to Amy Winehouse: 2 wds. |
| 33% | CYNDILAUPER | 11 | "Time After Time" singer who wrote the music and lyrics for the Broadway musical "Kinky Boots": 2 wds. |
| 33% | ANNEMURRAY | 10 | "You Needed Me" singer who was made a Companion of the Order of Canada in 1984: 2 wds. |
| 33% | JONIMITCHELL | 12 | "Big Yellow Taxi" singer who was made a Companion of the Order of Canada in 2002: 2 wds. |
| 33% | JELLYROLL | 9 | "Need a Favor" country singer who was nominated for Best New Artist at the 2024 Grammys: 2 wds. |
| 33% | DIONNEWARWICK | 13 | "That's What Friends Are For" singer who received a 2023 Kennedy Center Honor: 2 wds. |
| 33% | GARTHBROOKS | 11 | "Shameless" singer who is 33-Across's husband: 2 wds. |
| 33% | CELINEDION | 10 | "The Power of Love" singer who was made a Companion of the Order of Canada in 2008: 2 wds. |