| 100% | LITTLEBIG | 9 | ___ Town, country music group that won a Grammy for their hit song "Girl Crush": 2 wds. |
| 71% | CHICKS | 6 | The ___, country music group that won a Grammy for their hit song "Not Ready to Make Nice" |
| 62% | PERRY | 5 | The Band ___, country music group that won a Grammy for their cover of the song "Gentle on My Mind" |
| 60% | ZAC | 3 | ___ Brown Band, country music band that won a Grammy for their hit song "As She's Walking Away" |
| 48% | LINE | 4 | Florida Georgia ___, country music duo that won a Billboard Music Award for their hit song "Meant to Be" |
| 47% | ZACBROWNBAND | 12 | American country music band with the hit song "Colder Weather", that won the 2010 Grammy for Best New Artist: 3 wds. |
| 44% | SYSTEMOFADOWN | 13 | Group that won a Grammy for 2005's "B.Y.O.B": 4 wds. |
| 43% | BROKENHALOS | 11 | Chris Stapleton single that won the 2018 Grammy for Best Country Song: 2 wds. |
| 43% | SPACECOWBOY | 11 | Kacey Musgraves single that won the 2019 Grammy for Best Country Song: 2 wds. |
| 43% | VAMPIREWEEKEND | 14 | Indie rock band that won a Best Alternative Music Album Grammy in 2020 for "Father of the Bride": 2 wds. |
| 42% | AINTITFUN | 9 | Hit single by Paramore that won a Grammy Award for Best Rock Song in 2015 (3 wds.) |
| 42% | FAMILYTIES | 10 | 2021 Baby Keem and Kendrick Lamar hit that won a Grammy for Rap Performance: 2 wds. |
| 40% | BLACK | 5 | "___ Balloon," hit song by the Goo Goo Dolls from their album "Dizzy Up the Girl" that was nominated for a Grammy in 2000 |
| 40% | TLC | 3 | Girl group that won a Best R&B Album Grammy for "FanMail" |
| 40% | ALWAYSONMYMIND | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1983: 4 wds. |
| 40% | ONTHEROADAGAIN | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1981: 4 wds. |
| 39% | MIRANDALAMBERT | 14 | Ex-wife of Blake Shelton who won a Grammy for "The House That Built Me": 2 wds. |
| 39% | BETTERMAN | 9 | 2016 song written by Taylor Swift and performed by 33-Across that won a Grammy Award for Best Country Duo/Group Performance (2 wds.) |
| 39% | ELI | 3 | ___ Young Band, a country music band known for their hit song "Crazy Girl" |
| 39% | HOLIDAYINN | 10 | 1942 film that won a Best Original Song Oscar for 34-Across: 2 wds. |
| 39% | TLC | 3 | R&B group that won a Grammy for "No Scrubs" |
| 38% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |
| 38% | ABOUTDAMNTIME | 13 | 2022 Lizzo hit single that won a Grammy for Record of the Year (3 wds.) |
| 38% | HUMBLEANDKIND | 13 | Tim McGraw single that won the 2017 Grammy for Best Country Song: 3 wds. |
| 38% | FEELSLIKE | 9 | "___ Summer," hit song by Childish Gambino which was nominated for a Grammy: 2 wds. |
| 37% | IFIAINTGOTYOU | 13 | Song by 40-Across that won a Grammy for Best Female R&B Vocal Performance (5 wds.) |
| 37% | DIRESTRAITS | 11 | Music group with siblings as members with hit songs like "Sultans of Swing" and "Money for Nothing": 2 wds. |
| 37% | ONTHEROADAGAIN | 14 | Song by 30-Across/33-Across that won a Grammy Award for Best Country Song and was inducted into the Grammy Hall of Fame (4 wds.) |
| 37% | IFIAINTGOTYOU | 13 | 2004 18-Across hit that won a Grammy for Best Female R&B Vocal Performance: 5 wds. |
| 37% | PENTATONIX | 10 | Quintet that won a Grammy for their a cappella version of "Dance of the Sugar Plum Fairy" |