| 100% | WHITECHRISTMAS | 14 | Oscar-winning Irving Berlin song that's a seasonal favorite: 2 wds. |
| 47% | SMASHHIT | 8 | Song that's a huge success: 2 wds. |
| 47% | WHITECHRISTMAS | 14 | Irivng Berlin song sung by 53-Across in 16-Across that won an Oscar for Best Original Song (2 wds.) |
| 43% | TIGHTENUP | 9 | 27-Across song that won a Grammy Award in 2011 (2 wds.) |
| 39% | GREENBOOK | 9 | 2018 drama starring Mahershala Ali that's one of six PG-13 films to win a Best Picture Oscar in the 21st century (2 wds.) |
| 39% | CHEEKTOCHEEK | 12 | Irving Berlin song recorded as a duet by Louis Armstrong and 48-Across (3 wds.) |
| 39% | HOLIDAYINN | 10 | 1942 film that won a Best Original Song Oscar for 34-Across: 2 wds. |
| 39% | WITCHYWOMAN | 11 | Eagles song that a sorceress might sing on Halloween?: 2 wds. |
| 39% | THEARTIST | 9 | 2011 mostly silent drama starring Jean Dujardin that's one of six PG-13 films to win a Best Picture Oscar in the 21st century (2 wds.) |
| 38% | RRR | 3 | 2022 Indian film that won a Best Song Oscar |
| 37% | LETITGO | 7 | "Frozen" song that won an Oscar for Best Original Song in 2014 (3 wds.) |
| 37% | PROUDMARY | 9 | 1971 Ike & Tina Turner hit that's a cover of a Creedence Clearwater Revival song: 2 wds. |
| 37% | IMNOT | 5 | With 49-Across, song that won 14-Across his Best Country Song Grammy: 2 wds. |
| 37% | DIAMONDDOGS | 11 | David Bowie song that should be listened to on a 60th wedding anniversary?: 2 wds. |
| 37% | COMETOGETHER | 12 | 1969 #1 Beatles song that was subject of a Chuck Berry plagiarism lawsuit: 2 wds. |
| 37% | MONSTERMASH | 11 | Bobby "Boris" Pickett song that a vampire or werewolf might sing on Halloween?: 2 wds. |
| 37% | CITYOFSTARS | 11 | "La La Land" song that won an Oscar for Best Original Song in 2017 (3 wds.) |
| 37% | STAYHIGH | 8 | Brittany Howard song that won the Grammy Award for Best Rock Song in 2021: 2 wds. |
| 37% | THETWIST | 8 | 34-Across song that went to #1 twice and launched a huge dance craze: 2 wds. |
| 37% | IRONMAN | 7 | 44-Across song that shares its title with a Robert Downey, Jr. superhero film: 2 wds. |
| 37% | ROUNDHERE | 9 | 1994 Counting Crows song that begins, "Step out the front door like a ghost": 2 wds. |
| 36% | BILLIEJEAN | 10 | 1983 Michael Jackson song that inspired a moonwalk dance craze: 2 wds. |
| 36% | THEENTERTAINER | 14 | Scott Joplin instrumental song that was a hit in 1974: 2 wds. |
| 36% | BESTACTOR | 9 | Oscar won by 21-Across for "The King's Speech": 2 wds. |
| 36% | ISME | 4 | "This ___," Keala Settle song that won the 2018 Golden Globe Award for Best Original Song: 2 wds. |
| 36% | THISLAND | 8 | Gary Clark Jr. song that won the Grammy Award for Best Rock Song in 2020: 2 wds. |
| 36% | LOSEYOURSELF | 12 | 2002 Eminem rap song that topped the Hot 100 for a record-tying 12 weeks: 2 wds. |
| 36% | ASIF | 4 | "Like that's a possibility!": 2 wds. |
| 36% | FIGHTFORYOU | 11 | "Judas and the Black Messiah" song that won an Oscar for Best Original Song in 2021 (3 wds.) |
| 36% | BADBLOOD | 8 | Taylor Swift/Kendrick Lamar song that won the 2015 MTV VMA for Video of the Year: 2 wds. |