| 100% | JERRYLEELEWIS | 13 | 82-year-old singer who is still leaving his fans "Breathless": 3 wds. |
| 50% | CHUBBYCHECKER | 13 | 76-year-old singer who is still doing "The Twist": 2 wds. |
| 49% | PAULMCCARTNEY | 13 | 76-year-old singer who is still in a "Band on the Run": 2 wds. |
| 44% | MARYJBLIGE | 10 | "Not Gon' Cry" singer who was one of Glamour's 2023 Women of the Year: 3 wds. |
| 44% | FRANKIEVALLI | 12 | 30-Across singer who turns 90 years old on May 3, 2024 (2 wds.) |
| 41% | BRIANHARMAN | 11 | American who was 36 years old when he won his first major golf tournament, the 2023 Open Championship (2 wds.) |
| 41% | SERGIOGARCIA | 12 | Spaniard who was 37 years old when he won his first major golf tournament, the 2017 Masters Tournament (2 wds.) |
| 41% | STEWARTCINK | 11 | American who was 36 years old when he won his first major golf tournament, the 2009 Open Championship (2 wds.) |
| 40% | NATKINGCOLE | 11 | Legendary singer who was 18-Across's father: 3 wds. |
| 39% | ARIANAGRANDE | 12 | "Positions" singer who was Billboard's 2018 Woman of the Year: 2 wds. |
| 39% | DOLLYPARTON | 11 | "Jolene" singer who was MusiCares Person of the Year in 2019: 2 wds. |
| 39% | ZACBROWNBAND | 12 | "My Old Man" singers who have been nominated for the Country Music Association Award for Vocal Group of the Year 14 times (3 wds.) |
| 38% | TONYBENNETT | 11 | 2018 AP Coach of the Year who shares his name with the singer of "I Left My Heart in San Francisco": 2 wds. |
| 38% | BILLIEEILISH | 12 | "Bad Guy" singer who was Billboard's 2019 Woman of the Year: 2 wds. |
| 38% | NEILDIAMOND | 11 | "Sweet Caroline" singer who was MusiCares Person of the Year in 2009: 2 wds. |
| 38% | OLIVIARODRIGO | 13 | "Good 4 U" singer who was Billboard's 2021 Woman of the Year: 2 wds. |
| 38% | JONIMITCHELL | 12 | "Both Sides Now" singer who was MusiCares Person of the Year in 2022: 2 wds. |
| 38% | NICOLASCAGE | 11 | "National Treasure" actor who will turn 60 years old in 2024 (2 wds.) |
| 38% | KEANUREEVES | 11 | "John Wick" actor who will turn 60 years old in 2024 (2 wds.) |
| 37% | MARTINANDLEWIS | 14 | Comedy duo who were famously estranged for many years: 3 wds. |
| 37% | LANADELREY | 10 | "West Coast" singer who was born Elizabeth Woolridge Grant: 3 wds. |
| 37% | KACEYMUSGRAVES | 14 | "Follow Your Arrow" singer who is one of Time's 2022 Women of the Year: 2 wds. |
| 37% | DIONNEWARWICK | 13 | "Walk On By" singer who was the Mouse on season 3 of "The Masked Singer": 2 wds. |
| 36% | AMYWINEHOUSE | 12 | "Rehab" singer who was one of Tony Bennett's duet partners on his "Duets II" album: 2 wds. |
| 36% | ARIANAGRANDE | 12 | 17-Across and 39-Across singer who was named Billboard's 2018 Woman of the Year (2 wds.) |
| 36% | JONBONJOVI | 10 | "Blaze of Glory" singer who has his own wine label, Hampton Water: 3 wds. |
| 36% | AGEGROUP | 8 | Set of people who are around the same number of years old: 2 wds. |
| 36% | RUSSELLCROWE | 12 | "A Beautiful Mind" actor who will turn 60 years old in 2024 (2 wds.) |
| 36% | TAYLORSWIFT | 11 | "Anti-Hero" singer who is nominated for a 2022 American Music Award for Artist of the Year (2 wds.) |
| 36% | TAYLORSWIFT | 11 | Seven-time Grammy-winning country and pop singer who was EW's 2010 Entertainer of the Year: 2 wds. |