| 100% | MICHELLEBRANCH | 14 | The Wreckers singer who appeared on "The Big Interview with Dan Rather" with her husband, Patrick Carney of the Black Keys (2 wds.) |
| 54% | JASONISBELL | 11 | Drive-By Truckers singer who appeared on "The Big Interview with Dan Rather" with his wife, singer/songwriter Amanda Shires (2 wds.) |
| 53% | JOHNFOGERTY | 11 | Creedence Clearwater Revival singer who appeared on "The Big Interview with Dan Rather" with his children, who recorded an album with him in 2020 (2 wds.) |
| 37% | GLORIAESTEFAN | 13 | "Coming Out of the Dark" singer who, with her husband Emilio, won the 2019 Gershwin Prize: 2 wds. |
| 37% | ALEXISSMITH | 11 | Singer/actress who appeared on the May 3, 1971, cover of Time Magazine with the headline "That Old Magic Relights Broadway" (2 wds.) |
| 36% | BEVERLYSILLS | 12 | Singer/songwriter who appeared on the November 22, 1971, cover of Time Magazine with the corner banner "America's Queen of Opera" (2 wds.) |
| 36% | JAMESTAYLOR | 11 | Singer/songwriter who appeared on the March 1, 1971, cover of Time Magazine with the headline "The New Rock: Bittersweet and Low" (2 wds.) |
| 36% | BRITNEYSPEARS | 13 | Singer who appears nude in the video of her 2008 single, "Womanizer": 2 wds. |
| 35% | MILEYCYRUS | 10 | Singer who appears nude in the video of her 2013 single, "Wrecking Ball": 2 wds. |
| 34% | CHADOCHOCINCO | 13 | Former name of an NFL player who appeared on "Dancing With the Stars" in 2010: 2 wds. |
| 34% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 33% | BRETMICHAELS | 12 | Rock singer with Poison who finished seventh on season 3 of "The Masked Singer" as the Banana: 2 wds. |
| 32% | MILEYCYRUS | 10 | "Wrecking Ball" singer who performs on the remix of 49-Across: 2 wds. |
| 32% | JESSEMCCARTNEY | 14 | Pop singer with Dream Street who was the runner-up on season 3 of "The Masked Singer" as the Turtle: 2 wds. |
| 32% | JIMMIEALLEN | 11 | "Best Shot" country singer who came in seventh place with partner Emma Slater on season 30 of "Dancing with the Stars" (2 wds.) |
| 31% | ARETHAFRANKLIN | 14 | Singer who spells out the title of her 1967 hit "Respect": 2 wds. |
| 31% | ARIANAGRANDE | 12 | Singer who spells out the title of her 2019 hit "NASA": 2 wds. |
| 31% | ERINANDREWS | 11 | Female sportscaster who appeared on "Dancing With the Stars": 2 wds. |
| 31% | JOHNLEGEND | 10 | "All of Me" singer who's back, along with Gwen Stefani, as a veteran coach on "The Voice": 2 wds. |
| 31% | IGGYAZALEA | 10 | "Fancy" singer featured on "Problem" who in 2014 became the second ever to be simultaneously #1 and #2 with her first two hits: 2 wds. |
| 31% | JONHAMM | 7 | "Mad Men" actor who appeared on the reality dating show "The Big Date" in 1996: 2 wds. |
| 31% | BOBBYRYDELL | 11 | "Volare" singer who was honored with a star on the Hollywood Walk of Fame in 2020 (2 wds.) |
| 31% | BILLNYE | 7 | TV "Science Guy" who appeared on "Dancing With the Stars" in 2013: 2 wds. |
| 31% | WARRENSAPP | 10 | Former NFL player who appeared on "Dancing With the Stars" in 2008: 2 wds. |
| 31% | DONNYOSMOND | 11 | Actor who was the Peacock on season 1 of "The Masked Singer": 2 wds. |
| 31% | TORISPELLING | 12 | Actress who was the Unicorn on season 1 of "The Masked Singer": 2 wds. |
| 31% | MARGARETCHO | 11 | Comedian who was the Poodle on season 1 of "The Masked Singer": 2 wds. |
| 30% | STEVIEWONDER | 12 | "Songs in the Key of Life" singer-songwriter who was born on May 13, 1950 (2 wds.) |
| 30% | QUEENLATIFAH | 12 | Singer who spells out the title of her 1994 hit "U.N.I.T.Y.": 2 wds. |
| 30% | ADAMLEVINE | 10 | Singer who appears nude in the video of Maroon 5's 2015 single, "This Summer": 2 wds. |