| 100% | CHUBBYCHECKER | 13 | 76-year-old singer who is still doing "The Twist": 2 wds. |
| 77% | PAULMCCARTNEY | 13 | 76-year-old singer who is still in a "Band on the Run": 2 wds. |
| 59% | ARIANAGRANDE | 12 | "Positions" singer who was Billboard's 2018 Woman of the Year: 2 wds. |
| 59% | DOLLYPARTON | 11 | "Jolene" singer who was MusiCares Person of the Year in 2019: 2 wds. |
| 59% | BILLIEEILISH | 12 | "Bad Guy" singer who was Billboard's 2019 Woman of the Year: 2 wds. |
| 59% | NEILDIAMOND | 11 | "Sweet Caroline" singer who was MusiCares Person of the Year in 2009: 2 wds. |
| 58% | OLIVIARODRIGO | 13 | "Good 4 U" singer who was Billboard's 2021 Woman of the Year: 2 wds. |
| 58% | JONIMITCHELL | 12 | "Both Sides Now" singer who was MusiCares Person of the Year in 2022: 2 wds. |
| 58% | KACEYMUSGRAVES | 14 | "Follow Your Arrow" singer who is one of Time's 2022 Women of the Year: 2 wds. |
| 57% | AGEGROUP | 8 | Set of people who are around the same number of years old: 2 wds. |
| 57% | TAYLORSWIFT | 11 | Seven-time Grammy-winning country and pop singer who was EW's 2010 Entertainer of the Year: 2 wds. |
| 57% | JENNIFERLOPEZ | 13 | "Let's Get Loud" singer who was named Glamour Woman of the Year in 1999 and 2011: 2 wds. |
| 56% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 55% | JERRYLEELEWIS | 13 | 82-year-old singer who is still leaving his fans "Breathless": 3 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. |
| 53% | ARIANAGRANDE | 12 | 17-Across and 39-Across singer who was named Billboard's 2018 Woman of the Year (2 wds.) |
| 53% | PAULSIMON | 9 | Singer who performed "Still Crazy After All These Years" on the SNL40 anniversary special: 2 wds. |
| 52% | LENAHORNE | 9 | Jazz singer who was awarded the Spingarn Medal in 1983: 2 wds. |
| 52% | BRUNOMARS | 9 | "Grenade" singer who was the featured vocalist on "Uptown Funk": 2 wds. |
| 52% | JUSTINBIEBER | 12 | "Yummy" singer who was half the duet on 27-Across: 2 wds. |
| 52% | TAYLORSWIFT | 11 | "Anti-Hero" singer who is nominated for a 2022 American Music Award for Artist of the Year (2 wds.) |
| 52% | LEANNRIMES | 10 | Singer who is the youngest ever individual artist to win the Grammy: 2 wds. |
| 51% | BOBMARLEY | 9 | Singer whom 15-Across claims to be the reincarnation of: 2 wds. |
| 51% | BRUNOMARS | 9 | Singer who did the vocals on "Uptown Funk": 2 wds. |
| 51% | THOMASRHETT | 11 | 17-Across and 28-Across singer who was the 2019 Academy of Country Music's Male Artist of the Year (2 wds.) |
| 51% | RITCHIEVALENS | 13 | Rock singer who was the subject of the 1987 biopic "La Bamba": 2 wds. |
| 50% | ARIANAGRANDE | 12 | "7 Rings" singer who was half the duet on 27-/31-Across: 2 wds. |
| 50% | BENBERNANKE | 11 | Economist who was Time's 2009 Person of the Year: 2 wds. |
| 50% | JOHNNYCASH | 10 | Country singer who was the subject of the 2005 biopic "Walk the Line": 2 wds. |
| 50% | JAMESBROWN | 10 | Rock singer who was the subject of the 2014 biopic "Get On Up": 2 wds. |