| 100% | IBELIEVEICANFLY | 15 | Grammy-winning R. Kelly hit of 1996 |
| 50% | OUTOFTIME | 9 | Grammy-winning R.E.M. album of 1991 |
| 50% | CHER | 4 | A grammy winning singer nicknamed the "Goddess of Pop," who sang the hit song "Believe" |
| 50% | BEATIT | 6 | 1983 hit that won a Grammy for Record of the Year |
| 48% | VOLARE | 6 | 1958 hit that won the first-ever Grammy for Song of the Year |
| 48% | ROSANNA | 7 | Toto hit song that won the 1982 Grammy for Record of the Year |
| 47% | HELLO | 5 | Hit song by Adele that won 3 Grammy awards including Record of the Year in 2017 |
| 47% | IRONIC | 6 | Alanis Morissette hit of 1996 |
| 47% | BLACKHOLESUN | 12 | Grammy-winning Soundgarden hit of 1994 |
| 47% | ABOUTDAMNTIME | 13 | 2022 Lizzo hit single that won a Grammy for Record of the Year (3 wds.) |
| 47% | DIP | 3 | "Da' ___" (Freak Nasty hit of 1996) |
| 46% | ASHANTI | 7 | Grammy-winning R&B singer of "Foolish" |
| 46% | BAD | 3 | With 7-Down, Billie Eilish hit that won the 2020 Grammy for Song of the Year |
| 46% | THIS | 4 | "___ is America," hit song by Childish Gambino which won the Grammy for Record of the Year |
| 46% | ADELE | 5 | Grammy winning singer of "Hello" |
| 45% | IFIAINTGOTYOU | 13 | 2004 18-Across hit that won a Grammy for Best Female R&B Vocal Performance: 5 wds. |
| 45% | WEAREYOUNG | 10 | #1 fun. hit released in 2011 that won the Grammy for Song of the Year: 3 wds. |
| 45% | HIGHERLOVE | 10 | 1986 #1 hit for 30-Across, which won the Grammy for Record of the Year: 2 wds. |
| 45% | HALO | 4 | Grammy-winning Beyoncé hit of 2009 |
| 44% | IBELIEVEICANFLY | 15 | R. Kelly hit from "Space Jam" |
| 44% | DOVER | 5 | "Cliffs of ___," Grammy-winning instrumental hit by Eric Johnson |
| 44% | ROLLING | 7 | "___ in the Deep," hit song by Adele that won 3 Grammy awards including Record of the Year in 2012 |
| 43% | BEAT | 4 | "___ It," a hit single from Michael Jackson's album in 16a that won a Grammy for "Record of the Year" |
| 42% | DIARY | 5 | "The ___ of Alicia Keys" (R&B album that won three Grammy Awards) |
| 42% | CELINEDION | 10 | Singer whose 1996 album "Falling into You" won Grammy Awards for Album of the Year and Best Pop Album (2 wds.) |
| 42% | REMIX | 5 | R. Kelly's "Ignition" has a hit one |
| 42% | SINGININTHERAIN | 15 | Title hit of a 1952 Gene Kelly musical |
| 42% | CALIFORNIA | 10 | "Hotel ___," Grammy-winning song by the Eagles which is one of their biggest commercial hits |
| 41% | HER | 3 | R&B artist with the Grammy-winning 2017 hit "Best Part" |
| 41% | IBELIEVEICANFLY | 15 | R. Kelly hit whose last title word is aptly rhymed with "sky" in the lyrics ... and a hint to the starts of the other four longest puzzle answers |