| 100% | RAIN | 4 | "___ on Me," 2020 Lady Gaga and Ariana Grande song that won the Best Pop Duo Performance at the 63rd Grammy Awards |
| 58% | RAIN | 4 | "___ On Me," song by Lady Gaga and Ariana Grande that won the MTV Video Music Award for Song of the Year in 2020 |
| 54% | KISSMEMORE | 10 | 50-Across and SZA hit single that won Best Pop Duo/Group Performance at the 2022 Grammy Awards (3 wds.) |
| 48% | MORE | 4 | "Kiss Me ___," song by Doja Cat ft. SZA that won the Grammy Award for the Best Pop Duo/Group Performance in 2022 |
| 48% | TOWN | 4 | "Old ___ Road," song by Lil Nas X featuring Billy Ray Cyrus that won the Grammy Award for Best Pop Duo/Group Performance in 2020 |
| 46% | TRUTHHURTS | 10 | Viral 46-Across song that won the 2020 Grammy Award for Best Pop Solo Performance (2 wds.) |
| 45% | RAIN | 4 | "___ On Me," 2020 song from "Chromatica" that was a collab between Lady Gaga and Ariana Grande |
| 45% | TRUTH | 5 | "___ Hurts," song by Lizzo that won the Grammy Award for Best Pop Solo Performance in 2020 |
| 44% | TRUTHHURTS | 10 | 1-Across hit that won Best Pop Solo Performance at the 2020 Grammy Awards: 2 wds. |
| 43% | RAIN | 4 | "___ On Me," song by Ariana Grande and Lady Gaga ... or a shower from above that may fill up the water bodies mentioned in this puzzle |
| 43% | OLDTOWNROAD | 11 | Song for which Lil Nas X and Billy Ray Cyrus won the Grammy for Best Pop Duo/Group Performance in 2020: 3 wds. |
| 40% | DUET | 4 | Song such as Lady Gaga and Ariana Grande's "Rain on Me" |
| 38% | SAYSOMETHING | 12 | Song for which A Great Big World and Christina Aguilera won the Grammy for Best Pop Duo/Group Performance in 2015: 2 wds. |
| 37% | 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.) |
| 37% | SHALLOW | 7 | Lady Gaga and Bradley Cooper song from "A Star Is Born" that won the Oscar for Best Original Song in 2019 |
| 37% | THISLAND | 8 | Gary Clark Jr. song that won the Grammy Award for Best Rock Song in 2020: 2 wds. |
| 36% | WAITING | 7 | "___ on a War," song by Foo Fighters that won the Grammy Award for Best Rock song in 2022 |
| 36% | YOU | 3 | "Someone like ___," hit song by Adele that won the Grammy for Best Pop Solo Performance in 2012 |
| 36% | MAKING | 6 | "___ a Fire," song by Foo Fighters that won the Grammy Award for Best Rock Performance in 2022 |
| 35% | LIVIN | 5 | "While I'm ___," album by Tanya Tucker that won the Grammy Award for Best Country Album in 2020 |
| 35% | IGOR | 4 | Tyler, the Creator album that won Best Rap Album at the 2020 Grammy Awards |
| 35% | TRUTH | 5 | "___ Hurts," song by Lizzo which won the 2020 Grammy for Best Pop Solo Performance |
| 35% | MAN | 3 | "___! I Feel Like a Woman!" 1999 Shania Twain song that won a Grammy Award for Best Female Country Vocal Performance |
| 35% | STRESSEDOUT | 11 | Song for which Twenty One Pilots won the Grammy for Best Pop Duo/Group Performance in 2017: 2 wds. |
| 34% | STUCKWITHU | 10 | Single by Ariana Grande and 29-Across that debuted at No. 1 on the "Billboard" Top 100 in 2020 (3 wds.) |
| 34% | NEEDTOKNOW | 10 | Hit single by 50-Across that was nominated for Best Melodic Rap Performance at the 2022 Grammy Awards (3 wds.) |
| 34% | RINGS | 5 | "7 ___," number-one hit song by Ariana Grande which was nominated for Record of the Year at the 62nd Grammy Awards |
| 34% | MYFAITHINYOU | 12 | "If I Ever Lose ___," single that won Sting a Grammy Award for Best Pop Vocal Performance (Male) in 1994: 4 wds. |
| 34% | MENATWORK | 9 | 15-Across and 33-Across rock band from Australia that won Best New Artist at the 1983 Grammy Awards (3 wds.) |
| 33% | DONTLETMEDOWN | 13 | The Chainsmokers song that won the 2017 Grammy Award for Best Dance Recording (4 wds.) |