| 100% | DROPS | 5 | "___ of Jupiter" (Grammy-winning song by Train) |
| 74% | HELLO | 5 | 2015 song by Adele that won the Grammy Award for Record of the Year |
| 73% | DROPS | 5 | "___ of Jupiter," 2001 song by Train |
| 72% | HELLO | 5 | Hit song by Adele that won 3 Grammy awards including Record of the Year in 2017 |
| 72% | THIS | 4 | "___ is America," hit song by Childish Gambino which won the Grammy for Record of the Year |
| 71% | IWANTED | 7 | "Everything ___," song by Billie Eilish which won the Grammy for Record of the Year in 2021: 2 wds. |
| 70% | LEAVE | 5 | "___ the Door Open," song by Silk Sonic that won the Grammy Award for Song of the Year in 2022 |
| 70% | ROLLING | 7 | "___ in the Deep," hit song by Adele that won 3 Grammy awards including Record of the Year in 2012 |
| 70% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 66% | 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.) |
| 61% | BUTTERFLIES | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Solo Performance |
| 61% | JEROME | 6 | Song by Lizzo which won the 2020 Grammy for Best Traditional R&B Performance |
| 60% | ALLEY | 5 | "___ Cat," instrumental song by Bent Fabric which won a Grammy in 1963 |
| 60% | NINE | 4 | Number of Grammy Awards won by 12-Down |
| 60% | TEN | 3 | Number of Grammy Awards won by Bonnie Raitt |
| 60% | TEN | 3 | Number of Grammy Awards won by Taylor Swift |
| 60% | SPACECOWBOY | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Song (2 wds.) |
| 59% | RIVER | 5 | "Cry Me a ___," 2002 song by Justin Timberlake which won a Grammy Award |
| 59% | GRAMMY | 6 | Song of the Year award won by Lorde for 36-Across |
| 59% | REHAB | 5 | 2008 Grammy Song of the Year by Amy Winehouse |
| 59% | SWEETLOVE | 9 | Grammy-winning song by Anita Baker |
| 59% | CALIFORNIA | 10 | "Hotel ___," Grammy-winning song by the Eagles which is one of their biggest commercial hits |
| 59% | LAYLA | 5 | A hit song by Eric Clapton titled after a lady, that won a Grammy |
| 59% | WHAT | 4 | "___ Goes Around...Comes Around," 2006 song by Justin Timberlake which won a Grammy award |
| 59% | TRUTH | 5 | "___ Hurts," song by Lizzo which won the 2020 Grammy for Best Pop Solo Performance |
| 59% | DANI | 4 | "___ California," 2006 song by the Red Hot Chili Peppers that won two Grammy awards |
| 58% | VIVALAVIDA | 10 | 2009 Grammy Song of the Year by Coldplay: 3 wds. |
| 58% | JAIL | 4 | Song by Kanye featuring Jay-Z that won the Grammy Award for Best Rap Song in 2022 |
| 58% | TOGETHER | 8 | "We Belong ___," song by Mariah Carey that won the Grammy for Best R&B Song |
| 58% | CHER | 4 | A grammy winning singer nicknamed the "Goddess of Pop," who sang the hit song "Believe" |