| 100% | JOHNDENVER | 10 | Singer of "Take Me Home, Country Roads", who hosted 5 Grammy Award ceremonies: 2 wds. |
| 49% | JOHN | 4 | ___ Denver, singer of "Take Me Home, Country Roads" who might have just been homesick |
| 37% | KEITHURBAN | 10 | "Blue Ain't Your Color" singer who hosted the socially distant 2020 Academy of Country Music Awards: 2 wds. |
| 36% | JONSTEWART | 10 | Comedian who was the host of "The Daily Show" till 2015, and has hosted 2 Grammy Award ceremonies: 2 wds. |
| 36% | ROSIEODONNELL | 13 | Host of a self-titled talk show who hosted the 1999 and 2000 Grammy ceremonies: 2 wds. |
| 35% | DIERKSBENTLEY | 13 | Singer of 15-Across and 29-Across who was awarded the 2018 Academy of Country Music's Merle Haggard Spirit Award (2 wds.) |
| 35% | DIERKSBENTLEY | 13 | Singer of 15-Across and 29-Across who was honored with an Academy of Country Music's Merle Haggard Spirit Award (2 wds.) |
| 35% | PHIL | 4 | ___ Collins, singer of "Take Me Home" who might have just been homesick |
| 35% | DEBBIEHARRY | 11 | Lead singer of Blondie who received the first Billboard Women in Music Icon Award, in 2008: 2 wds. |
| 35% | MARK | 4 | ___ Strong, actor who sang a section of "Take Me Home, Country Roads" in "Kingsman: The Golden Circle" |
| 34% | DENVER | 6 | John ___, American singer-songwriter who sang "Take Me Home, Country Roads" |
| 34% | PAULREISER | 10 | "Mad About You" costar who hosted the 1995 Grammy ceremony: 2 wds. |
| 33% | REBAMCENTIRE | 12 | Grammy-winning country star who plays a singer on 32-Across: 2 wds. |
| 33% | ALISONKRAUSS | 12 | "Raising Sand" singer who won five Grammy Awards in 2009: 2 wds. |
| 33% | JONIMITCHELL | 12 | Singer of 5-Down and 7-Down who turns 75 on November 7, 2018 (2 wds.) |
| 33% | SELENAGOMEZ | 11 | Singer of "Lose You to Love Me" who has 179 million Instagram followers: 2 wds. |
| 33% | ALANJACKSON | 11 | "Country Boy" singer who won the CMA Award for Entertainer of the Year three times: 2 wds. |
| 32% | WALKERHAYES | 11 | Singer of the 2021 country song "AA": 2 wds. |
| 32% | WVA | 3 | "Take Me Home, Country Roads" subj. |
| 32% | WESTVIRGINIA | 12 | "Take Me Home, Country Roads" state |
| 32% | DEMILOVATO | 10 | "Sorry Not Sorry" singer who hosted the People's Choice Awards in 2020: 2 wds. |
| 32% | AMYWINEHOUSE | 12 | "Back to Black" singer who won five Grammy Awards in 2008: 2 wds. |
| 32% | LITTLEBIGTOWN | 13 | "Better Man" singers who have won the Country Music Association Award for Vocal Group of the Year six times (3 wds.) |
| 32% | TAYLORSWIFT | 11 | Singer of "Me!" who has 134 million Instagram followers: 2 wds. |
| 32% | SAMSMITH | 8 | Singer of the 2014 hit "Stay With Me": 2 wds. |
| 32% | DENVER | 6 | "Take Me Home, Country Roads" artist John |
| 31% | BLUERIDGE | 9 | Range mentioned in "Take Me Home, Country Roads" |
| 31% | LAURIEANDERSON | 14 | "O Superman" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 31% | 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.) |
| 31% | LUKECOMBS | 9 | Singer of the 2019 country hit "Beer Never Broke My Heart": 2 wds. |