| 100% | TROUBLE | 7 | Pink's Grammy-winning song that also featured in "Miss Congeniality 2: Armed and Fabulous" |
| 37% | STAYHIGH | 8 | Brittany Howard song that won the Grammy Award for Best Rock Song in 2021: 2 wds. |
| 37% | THISLAND | 8 | Gary Clark Jr. song that won the Grammy Award for Best Rock Song in 2020: 2 wds. |
| 35% | TIGHTENUP | 9 | 27-Across song that won a Grammy Award in 2011 (2 wds.) |
| 35% | LONELYBOY | 9 | 27-Across song that won two Grammy Awards in 2013 (2 wds.) |
| 35% | JAIL | 4 | Song by Kanye featuring Jay-Z that won the Grammy Award for Best Rap Song in 2022 |
| 32% | ISLANDSIN | 9 | With 40-Across, song that reached #1 on Billboard's country and Hot 100 charts in 1983: 2 wds. |
| 32% | ARMED | 5 | "Miss Congeniality 2: __ and Fabulous" |
| 32% | 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 |
| 32% | 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 |
| 32% | ARMED | 5 | "Miss Congeniality 2: ___ and Fabulous" (2005 movie) |
| 32% | ARMED | 5 | "Miss Congeniality 2: ___ and Fabulous" (2005 sequel) |
| 31% | ARMED | 5 | "Miss Congeniality 2: ___ and Fabulous" (Sandra Bullock movie) |
| 31% | GIGI | 4 | ___ Fernandez and Mary Joe Fernandez, tennis pair that won 2 consecutive Olympic gold medals in women's doubles |
| 31% | ARMED | 5 | "Miss Congeniality 2: ___ and Fabulous" (2005 Sandra Bullock sequel) |
| 31% | HEREWITHME | 10 | 2019 hit song by 17-Down featuring Chvrches with the lyrics "You're saying the words that I want you to say / There's a pain in my heart and it won't go away" (3 wds.) |
| 31% | HELLO | 5 | Adele song that won Record of the Year and Song of the Year Grammy Awards |
| 31% | IMNOT | 5 | With 49-Across, song that won 14-Across his Best Country Song Grammy: 2 wds. |
| 31% | NEWKIDINTOWN | 12 | 1976 Eagles song that won the Best Arrangement for Voices Grammy in 1977: 4 wds. |
| 31% | SAYONARA | 8 | Song played in the first and last episodes of "M*A*S*H" that's also called the "Japanese 32-Across Song" |
| 30% | REBELYELL | 9 | 42-Across hit song that is featured in Metal Gear, Guitar Hero, and WWE video games (2 wds.) |
| 30% | DONTWANNAFIGHT | 14 | Alabama Shakes song that won the Grammy Award for Best Rock Song in 2016: 3 wds. |
| 30% | FUNK | 4 | "Uptown ___," song by Mark Ronson featuring Bruno Mars that won 2 Grammys |
| 30% | WARTS | 5 | Bumps that are often seen on toads and also a feature of Shrek's anatomy as an ogre in the book |
| 30% | HELLO | 5 | Adele song that won the 2016 Record of the Year and Song of the Year Grammy Awards |
| 30% | ARLOPARKS | 9 | Grammy-nominated singer/songwriter whose songs 15-Across, 9-Down, and 27-Down are featured on her debut album, "Collapsed in Sunbeams" (2 wds.) |
| 30% | ONLY | 4 | "___ Fools and Horses," British TV series that featured the Pink Floyd song "Money" |
| 30% | JUDAS | 5 | "___ and the Black Messiah," film starring Daniel Kaluuya that won 2 Oscars in 2021 |
| 30% | GREATWALL | 9 | Landmark that, in a way, is a border feature of this puzzle and a hint to what's missing from 10 answers |
| 29% | BROKENHALOS | 11 | Chris Stapleton single that won the 2018 Grammy for Best Country Song: 2 wds. |