| 100% | TOBYKEITH | 9 | Singer (with Willie Nelson) of the 2003 song "Beer for My Horses": 2 wds. |
| 74% | TOBYKEITH | 9 | Singer who duetted with Willie Nelson on the 2003 #1 country hit "Beer for My Horses": 2 wds. |
| 51% | STEVIEWONDER | 12 | American singer with 25 Grammy Awards famous for his song "You Are the Sunshine of My Life": 2 wds. |
| 48% | PETERCETERA | 11 | Singer with the 1986 #1 song “Glory of Love”: 2 wds. |
| 48% | GARTHBROOKS | 11 | Singer of the 2000 song "Wild Horses": 2 wds. |
| 48% | TAYLORSWIFT | 11 | Singer of the 2008 song "White Horse": 2 wds. |
| 48% | KATYPERRY | 9 | Singer of the 2013 song "Dark Horse": 2 wds. |
| 47% | PHILCOLLINS | 11 | Singer with the 1988 #1 song “Groovy Kind of Love”: 2 wds. |
| 46% | SAMSMITH | 8 | Singer of the theme song for the Bond movie "Spectre": 2 wds. |
| 46% | TOMJONES | 8 | Singer of the theme song for the Bond movie "Thunderball": 2 wds. |
| 45% | BILLIEEILISH | 12 | Singer of the theme song for the Bond movie "No Time to Die": 2 wds. |
| 45% | TWILIGHTTIME | 12 | The Platters song covered by Willie Nelson with the lyric "When purple colored curtains mark the end of the day" (2 wds.) |
| 43% | DOLLYPARTON | 11 | Singer of the title song for the 1980 film "9 to 5" (2 wds.) |
| 43% | KENNYLOGGINS | 12 | Singer of the title song for the 1984 film "Footloose" (2 wds.) |
| 42% | 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. |
| 42% | SHEENAEASTON | 12 | Singer of the title song for the 1981 film "For Your Eyes Only" (2 wds.) |
| 42% | SHEENAEASTON | 12 | Singer of the James Bond theme song "For Your Eyes Only": 2 wds. |
| 41% | ELLIEGOULDING | 13 | Singer of the 2011 song "Lights": 2 wds. |
| 41% | ALJARREAU | 9 | Singer whose "Moonlighting" was the theme song for the TV show of the same name: 2 wds. |
| 41% | DAVIDCOOK | 9 | Singer of the 2008 song "Light On": 2 wds. |
| 41% | BRYANADAMS | 10 | Singer with the 1985 top 10 hit "Summer of '69": 2 wds. |
| 40% | KIDROCK | 7 | Rap and country singer with the song "Bawitdaba": 2 wds. |
| 40% | KANYEWEST | 9 | Singer of the 2010 song "All of the Lights": 2 wds. |
| 40% | NICKIMINAJ | 10 | Singer of the buttocks-themed song "Anaconda": 2 wds. |
| 40% | KELLYCLARKSON | 13 | Singer of the 2015 hit "Heartbeat Song": 2 wds. |
| 40% | RACHELPLATTEN | 13 | Singer of the 2015 hit "Fight Song": 2 wds. |
| 40% | SARABAREILLES | 13 | Singer of the 2007 hit "Love Song": 2 wds. |
| 40% | WALKERHAYES | 11 | Singer of the 2021 country song "AA": 2 wds. |
| 40% | MEGHANTRAINOR | 13 | Singer of the 2016 dance song "NO": 2 wds. |
| 40% | SAMSMITH | 8 | Singer of the 2014 hit "Stay With Me": 2 wds. |