| 100% | PAULSIMON | 9 | One of the singers of "Bridge Over Troubled Water," the 1972 campaign song for George McGovern: 2 wds. |
| 48% | PAULSIMON | 9 | American artist who has won the Grammy thrice for "Best Album of the Year," including one for "Bridge over Troubled Water": 2 wds. |
| 40% | BILLIEEILISH | 12 | Singer of the theme song for the Bond movie "No Time to Die": 2 wds. |
| 40% | KATYPERRY | 9 | Singer of "Roar," a 2016 campaign song for Hillary Clinton: 2 wds. |
| 40% | SAMSMITH | 8 | Singer of the theme song for the Bond movie "Spectre": 2 wds. |
| 40% | TOMJONES | 8 | Singer of the theme song for the Bond movie "Thunderball": 2 wds. |
| 38% | TOBYKEITH | 9 | Singer (with Willie Nelson) of the 2003 song "Beer for My Horses": 2 wds. |
| 38% | SHEENAEASTON | 12 | Singer of the title song for the 1981 film "For Your Eyes Only" (2 wds.) |
| 37% | DIANAROSS | 9 | "Stop! In the Name of Love" singer named one of People's Most Beautiful for 2017: 2 wds. |
| 37% | DOLLYPARTON | 11 | Singer of the title song for the 1980 film "9 to 5" (2 wds.) |
| 37% | CHUCKBERRY | 10 | American songwriter who was one of the pioneers of Rock and Roll and was known for his song "Johnny B. Goode": 2 wds. |
| 37% | KENNYLOGGINS | 12 | Singer of the title song for the 1984 film "Footloose" (2 wds.) |
| 37% | ALJARREAU | 9 | Singer whose "Moonlighting" was the theme song for the TV show of the same name: 2 wds. |
| 37% | SHEENAEASTON | 12 | Singer of the James Bond theme song "For Your Eyes Only": 2 wds. |
| 37% | TONYBENNETT | 11 | "Rags to Riches" singer who won the 2017 Library of Congress Gershwin Prize for Popular Song: 2 wds. |
| 36% | HELENREDDY | 10 | Australian-American singer whose 1972 song became an anthem for the women's liberation movement: 2 wds. |
| 36% | KENNYCHESNEY | 12 | "Come Over" singer who won the CMA Award for Entertainer of the Year four times: 2 wds. |
| 36% | STEVIEWONDER | 12 | American singer with 25 Grammy Awards famous for his song "You Are the Sunshine of My Life": 2 wds. |
| 35% | PAULMCCARTNEY | 13 | One of the two singers on 15-Across: 2 wds. |
| 35% | DIANAROSS | 9 | American singer who was the lead singer of "The Supremes" and is known for her solo songs like "Upside Down": 2 wds. |
| 35% | CHRISSTAPLETON | 14 | "Starting Over" singer/songwriter who won the 2021 CMA Awards for Male Vocalist of the Year, Album of the Year, Single of the Year, and Song of the Year (2 wds.) |
| 35% | PETERCETERA | 11 | Singer with the 1986 #1 song “Glory of Love”: 2 wds. |
| 34% | KATYPERRY | 9 | Starting in 2010, pop singer with a song in the top 10 of the Billboard Hot 100 for 69 consecutive weeks: 2 wds. |
| 34% | ARTGARFUNKEL | 12 | Ivy Leaguer (he went to Columbia) who sang the 1970 #1 hit "Bridge Over Troubled Water" with Paul Simon: 2 wds. |
| 34% | ELLIEGOULDING | 13 | Singer of the 2011 song "Lights": 2 wds. |
| 34% | CHRISSTAPLETON | 14 | Singer whose "Starting Over" won the Grammy for Best Country Album in 2022: 2 wds. |
| 34% | JLO | 3 | Nickname of the singer known for "All I Have" and "On the Floor": 2 wds. |
| 34% | NANCYSINATRA | 12 | Singer of the James Bond theme song "You Only Live Twice": 2 wds. |
| 34% | GARTHBROOKS | 11 | Singer of the 2000 song "Wild Horses": 2 wds. |
| 34% | TAYLORSWIFT | 11 | Singer of the 2008 song "White Horse": 2 wds. |