| 100% | HOTLINEBLING | 12 | Lead single from Drake's fourth album "Views," that won him two Grammys in 2017: 2 wds. |
| 44% | SPACECOWBOY | 11 | Single from the album "Golden Hour" that won Best Country Song at the 2019 Grammys: 2 wds. |
| 41% | JEAN | 4 | "Billie ___," the second single from Michael Jackson's album in 16a, that won two Grammys and one American Music Award |
| 38% | WEFOUNDLOVE | 11 | Single from Rihanna's 6th studio album, a collaboration with DJ Calvin Harris, that won her a Grammy and was featured in "Sherlock" : 3 wds. |
| 38% | MACKTHEKNIFE | 12 | 1959 Bobby Darin hit that won him two Grammys: 3 wds. |
| 37% | BLANKSPACE | 10 | Second single from Taylor Swift's fifth album, that received three Grammy nominations, and had a part in the lyrics misheard by many: 2 wds. |
| 37% | IWISHYOUROSES | 13 | Lead single from 49-Across's 2023 album "Red Moon in Venus" (4 wds.) |
| 36% | NOWOR | 5 | With 44-Across, lead single from 4-Down's "Hopeless Fountain Kingdom" album: 2 wds. |
| 35% | RUNTHISTOWN | 11 | 2009 single from Jay-Z, featuring Rihanna and Kanye West, that won the trio many awards, including two Grammys and an Emmy : 3 wds. |
| 35% | DONOTDISTURB | 12 | Song from Drake's 2017 playlist, "More Life", where he reveals his struggles in daily life: 3 wds. |
| 34% | TEENAGEFEVER | 12 | Song from Drake's 2017 playlist, "More Life", that samples Jennifer Lopez's "If You Had My Love": 2 wds. |
| 34% | MOTIONSICKNESS | 14 | Single from 48-Across's album "Stranger in the Alps" (2 wds.) |
| 34% | IWILL | 5 | "___ Wait," Mumford & Sons track released as a lead single from their album "Babel": 2 wds. |
| 33% | GLORYDAYS | 9 | The fifth single from Springsteen's album mentioned in 17a, about a man recollecting good times: 2 wds. |
| 33% | GOODDAYS | 8 | SZA top 10 hit that was the lead single from her 2022 #1 album "SOS": 2 wds. |
| 33% | BEVERLYHILLS | 12 | Single from the album "Make Believe" that was 42-Across's first Top 10 hit (2 wds.) |
| 33% | SHAKEITOFF | 10 | The lead single from Taylor Swift's fifth album, that received 3 Grammy nominations, and stayed on the Hot 100 charts for 50 weeks: 3 wds. |
| 33% | BABYBOY | 7 | Chart-topping single from 31-Down's "Dangerously in Love" album (2 wds.) |
| 33% | HOLYGRAIL | 9 | Hit single from Jay-Z's 12th album, featuring vocals from Justin Timberlake, which won a Grammy in 2014: 2 wds. |
| 33% | BUTTERFLIES | 11 | Single from the album "Golden Hour" that won Best Country Solo Performance at the 2019 Grammys |
| 32% | CANTGETENOUGH | 13 | Lead single from 45-Across's 2024 album 27-Across (3 wds.) |
| 31% | GETLUCKY | 8 | Lead single from "Random Access Memories": 2 wds. |
| 31% | VAMPIREWEEKEND | 14 | Indie rock band that won a Best Alternative Music Album Grammy in 2020 for "Father of the Bride": 2 wds. |
| 30% | BRASSMONKEY | 11 | 1987 single from 44-Across's album "Licensed to Ill": 2 wds. |
| 30% | BEAT | 4 | "___ It," a hit single from Michael Jackson's album in 16a that won a Grammy for "Record of the Year" |
| 29% | LOSINGMY | 8 | With 26-Down, single from 15-Across that became R.E.M.'s biggest hit: 2 wds. |
| 29% | HEARTWANTS | 10 | "The ___ What It Wants," single from Selena Gomez's compilation album "For You": 2 wds. |
| 29% | WHOKNEW | 7 | Top 10 single from Pink's "I'm Not Dead" album: 2 wds. |
| 29% | NOTEARSLEFT | 11 | With 28-Across, lead single from the album "Sweetener": 3 wds. |
| 29% | SHOTA | 5 | "He ___ portrait that won him an award.": 2 wds. |