| 100% | PAPA | 4 | *"___ Was a Rollin' Stone," song covered by The Temptations that won a Grammy Award |
| 61% | 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.) |
| 58% | MAKING | 6 | "___ a Fire," song by Foo Fighters that won the Grammy Award for Best Rock Performance in 2022 |
| 57% | WAITING | 7 | "___ on a War," song by Foo Fighters that won the Grammy Award for Best Rock song in 2022 |
| 54% | TAKINGTHE | 9 | "___ Long Way," country album by The Chicks that won a Grammy Award in 2007: 2 wds. |
| 54% | OWN | 3 | "___ the Night," country album by Lady Antebellum that won a Grammy Award in 2012 |
| 53% | YOU | 3 | "I Will Remember ___," song by Canadian singer Sarah McLachlan that won her a Grammy Award |
| 52% | BLUE | 4 | "___ (Da Ba Dee)" a hit song by Eiffel 65 that won a Grammy award for "Best Dance Recording" |
| 52% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 51% | NAME | 4 | "You Don't Know My ___," 2003 song by Alicia Keys that won a Grammy Award for Best R&B Song |
| 51% | WAY | 3 | "Walk This ___," 1975 song by Aerosmith that was covered by Run-D.M.C and won a Soul Train Music Award |
| 50% | AINTITFUN | 9 | Hit single by Paramore that won a Grammy Award for Best Rock Song in 2015 (3 wds.) |
| 50% | LEAVE | 5 | "___ the Door Open," song by Silk Sonic that won the Grammy Award for Song of the Year in 2022 |
| 50% | NEVER | 5 | "___ Be the Same," hit song by Camila Cabello that won an iHeartRadio award in 2019 |
| 50% | ENSENADA | 8 | "The Road to ___," country album by Lyle Lovett that won a Grammy Award in 1997 |
| 50% | HELLO | 5 | 2015 song by Adele that won the Grammy Award for Record of the Year |
| 50% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 49% | JAIL | 4 | Song by Kanye featuring Jay-Z that won the Grammy Award for Best Rap Song in 2022 |
| 49% | SINGLE | 6 | "___ Ladies (Put a Ring on It)," 2008 song by Beyonce that won three Grammy Awards |
| 49% | 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 |
| 49% | HAVE | 4 | "___ a Cigar," Pink Floyd song that was covered by the Foo Fighters |
| 49% | TRUTH | 5 | "___ Hurts," song by Lizzo that won the Grammy Award for Best Pop Solo Performance in 2020 |
| 49% | HELLO | 5 | Hit song by Adele that won 3 Grammy awards including Record of the Year in 2017 |
| 49% | PERRY | 5 | The Band ___, country music group that won a Grammy for their cover of the song "Gentle on My Mind" |
| 48% | SHEENA | 6 | "___ Is a Punk Rocker," 1977 song by the Ramones that was covered by Charli XCX in 2016 |
| 48% | ROLLING | 7 | "___ in the Deep," hit song by Adele that won 3 Grammy awards including Record of the Year in 2012 |
| 47% | PLATINUM | 8 | County album by Miranda Lambert that won a Grammy Award in 2015 |
| 47% | INDUSTRYBABY | 12 | 2021 #1 song by Lil Nas X and 36-Across that was nominated for a Best Melodic Rap Performance Grammy Award and won three MTV Video Music Awards (2 wds.) |
| 47% | MORE | 4 | "Kiss Me ___," song by Doja Cat ft. SZA that won the Grammy Award for the Best Pop Duo/Group Performance in 2022 |
| 47% | TOOMANYRIVERS | 13 | Song by 17-Across covered by 40-Across that was a hit for Brenda Lee in the 1960s (3 wds.) |