| 100% | SYSTEMOFADOWN | 13 | Group that won a Grammy for 2005's "B.Y.O.B": 4 wds. |
| 58% | LITTLEBIG | 9 | ___ Town, country music group that won a Grammy for their hit song "Girl Crush": 2 wds. |
| 57% | TLC | 3 | R&B group that won a Grammy for "No Scrubs" |
| 54% | IFIAINTGOTYOU | 13 | Song by 40-Across that won a Grammy for Best Female R&B Vocal Performance (5 wds.) |
| 54% | WEAREINLOVE | 11 | 33-Across album that won a Grammy for Best Jazz Vocal Performance, Male (4 wds.) |
| 54% | GIRLONFIRE | 10 | Album by 40-Across that won a Grammy for Best R&B Album (3 wds.) |
| 53% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 53% | IFIAINTGOTYOU | 13 | 2004 18-Across hit that won a Grammy for Best Female R&B Vocal Performance: 5 wds. |
| 52% | TLC | 3 | Girl group that won a Best R&B Album Grammy for "FanMail" |
| 50% | CHICKS | 6 | The ___, country music group that won a Grammy for their hit song "Not Ready to Make Nice" |
| 49% | PERRY | 5 | The Band ___, country music group that won a Grammy for their cover of the song "Gentle on My Mind" |
| 49% | ABOUTDAMNTIME | 13 | 2022 Lizzo hit single that won a Grammy for Record of the Year (3 wds.) |
| 49% | 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 |
| 49% | 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.) |
| 48% | ALWAYSONMYMIND | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1983: 4 wds. |
| 48% | ONTHEROADAGAIN | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1981: 4 wds. |
| 48% | FAMILYTIES | 10 | 2021 Baby Keem and Kendrick Lamar hit that won a Grammy for Rap Performance: 2 wds. |
| 48% | SONGSIHEARD | 11 | 33-Across album that won a Grammy Award for Best Traditional Pop Vocal Album (3 wds.) |
| 48% | MYFAITHINYOU | 12 | "If I Ever Lose ___," single that won Sting a Grammy Award for Best Pop Vocal Performance (Male) in 1994: 4 wds. |
| 48% | AINTITFUN | 9 | Hit single by Paramore that won a Grammy Award for Best Rock Song in 2015 (3 wds.) |
| 47% | TIFFANYHADDISH | 14 | "The Last O.G." actress who won a Grammy for Best Comedy Album in 2021: 2 wds. |
| 47% | WHEREAREUNOW | 12 | 2015 Jack Ü/Justin Bieber hit that got a Grammy for Best Dance Recording: 4 wds. |
| 46% | ABOYNAMEDSUE | 12 | Johnny Cash song for which Shel Silverstein won a Grammy: 4 wds. |
| 46% | MIRANDALAMBERT | 14 | Ex-wife of Blake Shelton who won a Grammy for "The House That Built Me": 2 wds. |
| 46% | 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.) |
| 46% | CHAINOFFOOLS | 12 | Aretha Franklin's 1967 single that won her a Grammy for Best Female R&B Vocal Performance and later a Grammy Hall Of Fame Award: 3 wds. |
| 45% | THEFOGOFWAR | 11 | Documentary film based on Robert S. McNamara that won the Oscar for Best Documentary Feature in 2003: 4 wds. |
| 45% | NEWKIDINTOWN | 12 | 1976 Eagles song that won the Best Arrangement for Voices Grammy in 1977: 4 wds. |
| 45% | BAHA | 4 | ___ Men (group that won a Grammy Award in 2001 for Best Dance Recording) |
| 44% | DONTLETMEDOWN | 13 | Hit single from The Chainsmokers, featuring Daya, which won them a Grammy for Best Dance Recording: 4 wds. |