| 100% | NANCYSINATRA | 12 | "These Boots Were Made for Walkin'" singer who sang on an episode of "The Sopranos": 2 wds. |
| 54% | NANCYSINATRA | 12 | "Somethin' Stupid" singer who also sang 1965's "These Boots Are Made for Walkin'": 2 wds. |
| 47% | NANCYSINATRA | 12 | Performer with the 1966 hit "These Boots Are Made for Walkin'": 2 wds. |
| 47% | BILLIEEILISH | 12 | Singer-songwriter who sings "What Was I Made For?" on "Barbie: The Album" (2 wds.) |
| 44% | ANNIELENNOX | 11 | "Sweet Dreams (Are Made of This)" singer who was voted into the Songwriters Hall of Fame in 2020: 2 wds. |
| 43% | JAMESBROWN | 10 | Rock singer who was the subject of the 2014 biopic "Get On Up": 2 wds. |
| 43% | SINATRA | 7 | "These Boots Are Made for Walkin'" singer Nancy |
| 43% | PATTILABELLE | 12 | "New Attitude" singer who was the Flower on season 2 of "The Masked Singer": 2 wds. |
| 42% | ANNEMURRAY | 10 | "You Needed Me" singer who was made a Companion of the Order of Canada in 1984: 2 wds. |
| 42% | JONIMITCHELL | 12 | "Big Yellow Taxi" singer who was made a Companion of the Order of Canada in 2002: 2 wds. |
| 42% | ARIANAGRANDE | 12 | "7 Rings" singer who was both the host and musical guest on a 2016 "SNL" episode: 2 wds. |
| 42% | DAVIDGILMOUR | 12 | "On an Island" guitarist and singer who was inducted into the Rock and Roll Hall of Fame in 1996: 2 wds. |
| 42% | BILLIEEILISH | 12 | "Bad Guy" singer who was both the host and musical guest on a 2021 "Saturday Night Live" episode: 2 wds. |
| 42% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 41% | BILLIEEILISH | 12 | "What Was I Made For?" singer/co-songwriter who won Song of the Year at the 2024 Grammy Awards (2 wds.) |
| 41% | ISAACHAYES | 10 | "Soul Man" singer who won an Academy Award for Best Original Song for his work on the film "Shaft": 2 wds. |
| 41% | DIANAROSS | 9 | American singer who was the lead singer of "The Supremes" and is known for her solo songs like "Upside Down": 2 wds. |
| 40% | JENNIFERLOPEZ | 13 | "On the Floor" singer who's an executive producer and judge on "World of Dance": 2 wds. |
| 40% | SAMFISCHER | 10 | "This City" singer who sings "What Other People Say" with Demi Lovato on the 2021 album "Dancing with the Devil ... the Art of Starting Over" (2 wds.) |
| 39% | KELLYCLARKSON | 13 | "Miss Independent" singer who has been a coach on "The Voice" for the last five seasons (2 wds.) |
| 39% | BOBBYRYDELL | 11 | "Volare" singer who was honored with a star on the Hollywood Walk of Fame in 2020 (2 wds.) |
| 39% | THEWEEKND | 9 | Stage name of "Starboy" singer who used the name for anonymity on YouTube: 2 wds. |
| 39% | BOBMARLEY | 9 | Singer whom 15-Across claims to be the reincarnation of: 2 wds. |
| 39% | ENYA | 4 | One-name Irish singer who sang "May It Be" for "The Fellowship of the Ring" |
| 39% | TAYLORSWIFT | 11 | "Anti-Hero" singer who was honored with the People's Choice Award for The Female Artist of 2022 (2 wds.) |
| 39% | ELVISCOSTELLO | 13 | "Veronica" new wave singer who was honored with a star on the Hollywood Walk of Fame in 2020 (2 wds.) |
| 39% | TANYATUCKER | 11 | "Delta Dawn" country singer who was honored with a star on the Hollywood Walk of Fame in 2020 (2 wds.) |
| 39% | GLADYSKNIGHT | 12 | "Midnight Train to Georgia" singer who was the Bee on season 1 of "The Masked Singer": 2 wds. |
| 39% | SAMSMITH | 8 | Nonbinary singer who won an Oscar for the Bond theme "Writing's on the Wall": 2 wds. |
| 39% | ARIANAGRANDE | 12 | "Thank U Next" singer who sings "Met Him Last Night" with Demi Lovato on "Dancing with the Devil ... the Art of Starting Over" (2 wds.) |