100% | TAKINGTHE | 9 | "___ Long Way," country album by The Chicks that won a Grammy Award in 2007: 2 wds. |
57% | OWN | 3 | "___ the Night," country album by Lady Antebellum that won a Grammy Award in 2012 |
54% | ENSENADA | 8 | "The Road to ___," country album by Lyle Lovett that won a Grammy Award in 1997 |
51% | PARK | 4 | "Same Trailer, Different ___," country album by Kacey Musgraves that won a Grammy Award in 2014 |
50% | ROOM | 4 | "From A ___: Volume 1" country album by Chris Stapleton that won a Grammy Award in 2018 |
48% | PLATINUM | 8 | County album by Miranda Lambert that won a Grammy Award in 2015 |
47% | VAMPIREWEEKEND | 14 | Indie rock band that won a Best Alternative Music Album Grammy in 2020 for "Father of the Bride": 2 wds. |
46% | 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% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
43% | LIVIN | 5 | "While I'm ___," album by Tanya Tucker that won the Grammy Award for Best Country Album in 2020 |
43% | TIGHTENUP | 9 | 27-Across song that won a Grammy Award in 2011 (2 wds.) |
43% | SOUR | 4 | Album by Olivia Rodrigo that won the Grammy Award for Best Pop Vocal Album in 2022 |
43% | RAISINGSAND | 11 | Bluegrass album by Robert Plant and Alison Krauss that won Album of the Year at the 2009 Grammy Awards (2 wds.) |
42% | TIFFANYHADDISH | 14 | "Black Mitzvah" comedian who won a Grammy Award for Best Comedy Album in 2021 (2 wds.) |
42% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
42% | 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.) |
42% | AINTITFUN | 9 | Hit single by Paramore that won a Grammy Award for Best Rock Song in 2015 (3 wds.) |
42% | KILLINTIME | 10 | Album by 45-Across featuring the singles 18-Across and 26-Across that won the 1989 Album of the Year Academy of Country Music Award (2 wds.) |
41% | KATHYGRIFFIN | 12 | "Calm Down Gurrl" comedian who won a Grammy Award for Best Comedy Album in 2014 (2 wds.) |
41% | WHOOPIGOLDBERG | 14 | "Direct from Broadway" comedian who won a Grammy Award for Best Comedy Album in 1986 (2 wds.) |
41% | BRYANCRANSTON | 13 | "Breaking Bad" star who won a 2014 Tony Award for portraying Lyndon Johnson in "All the Way": 2 wds. |
40% | MORNINGPHASE | 12 | Beck album that won the 2015 Grammy Award for Best Rock Album: 2 wds. |
40% | THERESISTANCE | 13 | Muse album that won the 2011 Grammy Award for Best Rock Album: 2 wds. |
40% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
39% | WASTINGLIGHT | 12 | Foo Fighters album that won the 2012 Grammy Award for Best Rock Album: 2 wds. |
38% | STAYHIGH | 8 | Brittany Howard song that won the Grammy Award for Best Rock Song in 2021: 2 wds. |
38% | 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.) |
38% | FROMTHEFIRES | 12 | Greta Van Fleet album that won the Grammy Award for Best Rock Album in 2019 (3 wds.) |
38% | TIFFANYHADDISH | 14 | "The Last O.G." actress who won a Grammy for Best Comedy Album in 2021: 2 wds. |
38% | GIRLONFIRE | 10 | Album by 40-Across that won a Grammy for Best R&B Album (3 wds.) |