| 100% | NEED | 4 | "___ You Now" (Grammy-winning song by Lady A) |
| 84% | HONEY | 5 | "American ___," 2010 song by Lady A from the album "Need You Now" |
| 81% | NEED | 4 | "___ You Now" (Grammy-winning song by Lady Antebellum) |
| 73% | LAYLA | 5 | A hit song by Eric Clapton titled after a lady, that won a Grammy |
| 65% | WHERE | 5 | "___ Are U Now," song by Skrillex, Diplo and Justin Bieber which won a Grammy in 2016 |
| 64% | ALLEY | 5 | "___ Cat," instrumental song by Bent Fabric which won a Grammy in 1963 |
| 63% | NEED | 4 | "____ You Now" by Lady A |
| 63% | OWN | 3 | "___ the Night," country album by Lady Antebellum that won a Grammy Award in 2012 |
| 63% | WHAT | 4 | "___ Goes Around...Comes Around," 2006 song by Justin Timberlake which won a Grammy award |
| 62% | NOW | 3 | "Need You ___" (Grammy-winning song by Lady Antebellum) |
| 62% | IFIAINTGOTYOU | 13 | Song by 40-Across that won a Grammy for Best Female R&B Vocal Performance (5 wds.) |
| 62% | HONEY | 5 | "American ___," Lady A's song referring a natural sweetener in the album "Need You Now" |
| 62% | YOU | 3 | "I Will Remember ___," song by Canadian singer Sarah McLachlan that won her a Grammy Award |
| 61% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 60% | AWAY | 4 | "Give It ___," 1991 song by the Red Hot Chili Peppers which won a Grammy Award in 1992 |
| 60% | NAME | 4 | "You Don't Know My ___," 2003 song by Alicia Keys that won a Grammy Award for Best R&B Song |
| 60% | COMPASS | 7 | 2013 song by Lady A from the album "Golden" |
| 60% | MYWORLD | 7 | "Come into ___," hit song by Australian singer Kylie Minogue which won a Grammy Award in 2004: 2 wds. |
| 59% | PAPA | 4 | *"___ Was a Rollin' Stone," song covered by The Temptations that won a Grammy Award |
| 59% | WANTED | 6 | "___ You More," 2012 song by Lady A from the album "Own the Night" |
| 58% | HERE | 4 | "___ You Come Again," 1977 Dolly Parton song that won a Grammy for Best Female Country Vocal Performance |
| 57% | FRIDAY | 6 | "___ Night," 2011 song by Lady A from the album "Own the Night" |
| 57% | AINTITFUN | 9 | Hit single by Paramore that won a Grammy Award for Best Rock Song in 2015 (3 wds.) |
| 57% | SINGLE | 6 | "___ Ladies (Put a Ring on It)," 2008 song by Beyonce that won three Grammy Awards |
| 57% | ADORE | 5 | "___ You," hit song by Harry Styles which was nominated for a Grammy award |
| 57% | LOVE | 4 | "Be Patient With My ___," 2019 song by Lady A from the album "Ocean" |
| 56% | 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.) |
| 55% | STARTED | 7 | "Let's Get It ___," 2004 song by the Black Eyed Peas that won a Grammy for Best Rap Performance by a Duo or Group |
| 55% | IFEELFORYOU | 11 | Grammy-winning song written by Prince that was a #1 hit for Chaka Khan in 1984 (4 wds.) |
| 54% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |