| 100% | ENSENADA | 8 | "The Road to ___," country album by Lyle Lovett that won a Grammy Award in 1997 |
| 63% | OWN | 3 | "___ the Night," country album by Lady Antebellum that won a Grammy Award in 2012 |
| 56% | PARK | 4 | "Same Trailer, Different ___," country album by Kacey Musgraves that won a Grammy Award in 2014 |
| 55% | TAKINGTHE | 9 | "___ Long Way," country album by The Chicks that won a Grammy Award in 2007: 2 wds. |
| 55% | ROOM | 4 | "From A ___: Volume 1" country album by Chris Stapleton that won a Grammy Award in 2018 |
| 53% | PLATINUM | 8 | County album by Miranda Lambert that won a Grammy Award in 2015 |
| 48% | LIVIN | 5 | "While I'm ___," album by Tanya Tucker that won the Grammy Award for Best Country Album in 2020 |
| 47% | SOUR | 4 | Album by Olivia Rodrigo that won the Grammy Award for Best Pop Vocal Album in 2022 |
| 44% | ITISWHATITIS | 12 | Album by 41-Across featuring 17-Across that won the Grammy Award for Best Progressive R&B Album in 2021 (5 wds.) |
| 44% | LOST | 4 | "Call Me If You Get ___," album by Tyler, the Creator that won the Grammy Award for Best Rap Album in 2022 |
| 41% | TIGHTENUP | 9 | 27-Across song that won a Grammy Award in 2011 (2 wds.) |
| 41% | BAHA | 4 | ___ Men (group that won a Grammy Award in 2001 for Best Dance Recording) |
| 40% | MAKING | 6 | "___ a Fire," song by Foo Fighters that won the Grammy Award for Best Rock Performance in 2022 |
| 40% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 40% | 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.) |
| 40% | AINTITFUN | 9 | Hit single by Paramore that won a Grammy Award for Best Rock Song in 2015 (3 wds.) |
| 40% | VAMPIREWEEKEND | 14 | Indie rock band that won a Best Alternative Music Album Grammy in 2020 for "Father of the Bride": 2 wds. |
| 40% | THRILLER | 8 | Album by Michael Jackson and Quincy Jones that won the Grammy for Album of the Year in 1984 |
| 39% | COME | 4 | "The Best is Yet to ___," album by Ella Fitzgerald that won her the Grammy for Best Jazz Vocal Performance in 1984 |
| 39% | GIRL | 4 | 2019 album by 44-Across that won the Country Music Association's Album of the Year Award |
| 39% | NIGHTFALL | 9 | 2020 album by 33-Across that was nominated for a Best Country Album Grammy Award |
| 39% | HERO | 4 | 2016 album by 44-Across that was nominated for a Best Country Album Grammy Award |
| 39% | LYLE | 4 | Musician Lovett who won the Best Country Album Grammy in 1996 |
| 39% | WAITING | 7 | "___ on a War," song by Foo Fighters that won the Grammy Award for Best Rock song in 2022 |
| 39% | MELODRAMA | 9 | 2017 album by 53-Across that received a Grammy Award nomination for Album of the Year |
| 38% | HELLO | 5 | Hit song by Adele that won 3 Grammy awards including Record of the Year in 2017 |
| 38% | RAISINGSAND | 11 | Bluegrass album by Robert Plant and Alison Krauss that won Album of the Year at the 2009 Grammy Awards (2 wds.) |
| 38% | UNAPOLOGETIC | 12 | Seventh studio album by Rihanna, that won her a Grammy in 2014 and had global hits like "Diamonds" and "Stay" |
| 38% | CHICKS | 6 | The ___, country music group that won a Grammy for their hit song "Not Ready to Make Nice" |
| 38% | BOYGENIUS | 9 | Indie rock supergroup that won a Grammy for the 2023 album "The Record" |