| 100% | SUNDAY | 6 | "___ Mornin' Comin' Down," 1969 song cover by Johnny Cash that won Song of The Year at the CMAs |
| 42% | FLOWERS | 7 | Miley Cyrus song that won Record of the Year at the 2024 Grammys |
| 41% | FASTCAR | 7 | 1988 Tracy Chapman hit that won Song of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 41% | HURT | 4 | Original song by Nine Inch Nails that was covered by Johnny Cash in 2002 and won the Grammy for Best Short Form Music Video |
| 40% | YOU | 3 | "___ Are My Sunshine," 1969 song cover by Johnny Cash featured on the album "Unearthed" |
| 40% | BEEN | 4 | "I've ___ Everywhere," Geoff Mack song covered by Johnny Cash that lists all the places traveled by the singer |
| 39% | RAISINGSAND | 11 | Bluegrass album by Robert Plant and Alison Krauss that won Album of the Year at the 2009 Grammy Awards (2 wds.) |
| 38% | LIVES | 5 | "Best Years of Our ___," song covered by Baha Men that was featured in the "Shrek" franchise |
| 37% | CAR | 3 | "A Wednesday ___," song by Johnny Cash that celebrates the third day of the week |
| 37% | TAKE | 4 | "Every Breath You ___," song performed by the Police that won the Grammy for Song of the Year in 1984 |
| 36% | ROAR | 4 | Katy Perry song that lost Song of the Year at the 2013 Grammys |
| 35% | BLOOD | 5 | "Bad ___," song by Taylor Swift that won an MTV VMA for Video of the Year in 2015 |
| 35% | LEAVE | 5 | "___ the Door Open," song by Silk Sonic that won the Grammy Award for Song of the Year in 2022 |
| 35% | TRACYCHAPMAN | 12 | "Fast Car" songwriter who won Song of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 35% | HELLO | 5 | 2015 song by Adele that won the Grammy Award for Record of the Year |
| 35% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 34% | PIECEOFME | 9 | Song by 32-Across that won three MTV Video Music Awards in 2008, including Video of the Year (3 wds.) |
| 34% | HELLO | 5 | Hit song by Adele that won 3 Grammy awards including Record of the Year in 2017 |
| 34% | MIRANDALAMBERT | 14 | "Settling Down" singer who won Entertainer of the Year at the 2022 ACM Awards: 2 wds. |
| 34% | BILLIEEILISH | 12 | "What Was I Made For?" singer/co-songwriter who won Song of the Year at the 2024 Grammy Awards (2 wds.) |
| 34% | GRAMMY | 6 | Song of the Year award won by Lorde for 36-Across |
| 34% | PAPA | 4 | *"___ Was a Rollin' Stone," song covered by The Temptations that won a Grammy Award |
| 33% | ROLLING | 7 | "___ in the Deep," hit song by Adele that won 3 Grammy awards including Record of the Year in 2012 |
| 33% | BOXES | 5 | "Little ___," 1964 song covered by The Womenfolk that is one of the shortest songs to enter the Billboard charts |
| 33% | HELLO | 5 | Adele song that won Record of the Year and Song of the Year Grammy Awards |
| 33% | PERDONAME | 9 | Reggaeton song by the duo La Factoria and Eddy Lover that won the Urban Song of the Year in 2009 |
| 33% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 33% | MARENMORRIS | 11 | "The Bones" country singer who won Female Vocalist of the Year at the 2020 CMAs: 2 wds. |
| 33% | MIRANDALAMBERT | 14 | "Bluebird" country singer who won Music Video of the Year at the 2020 CMAs: 2 wds. |
| 32% | OLDDOMINION | 11 | "One Man Band" country band who won Vocal Group of the Year at the 2020 CMAs: 2 wds. |