| 100% | HEYYA | 5 | Outkast hit single of 2003 (2 wds.) |
| 65% | HEYYA | 5 | OutKast megahit of 2003: 2 wds. |
| 65% | HEYYA | 5 | 2003 OutKast hit: 2 wds. |
| 62% | HEYYA | 5 | OutKast hit that was #1 for nine weeks in 2003-2004: 2 wds. |
| 58% | HEYYA | 5 | 2003 hit for OutKast: 2 wds. |
| 52% | RAPGOD | 6 | Eminem song which holds the world record for most words in a hit single with an average of 4.28 words per second: 2 wds. |
| 51% | LUKASGRAHAM | 11 | Danish pop and soul band with the hit single "7 Years", that was nominated for Record of the Year in the 2017 Grammy Awards : 2 wds. |
| 50% | HEADABOVEWATER | 14 | 2019 album by 30-Across with the hit single of the same name (3 wds.) |
| 49% | BROWNSUGAR | 10 | #1 hit single from 31-Across with controversial lyrics: 2 wds. |
| 49% | OLIVIARODRIGO | 13 | Singer whose 2021 hit single "Drivers License" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 49% | POETICJUSTICE | 13 | Hit single from "Good Kid, M.A.A.D City" featuring Drake: 2 wds. |
| 49% | SOULMAN | 7 | Top-20 hit single for this puzzle's theme duo: 2 wds. |
| 49% | BILLIEJEAN | 10 | Title woman in a 1983 hit single by Michael Jackson: 2 wds. |
| 49% | PEGGYSUE | 8 | Title woman in a 1957 hit single by Buddy Holly: 2 wds. |
| 49% | KENNYCHESNEY | 12 | Country star with the 2010 hit single "Somewhere With You": 2 wds. |
| 49% | DEMONDAYS | 9 | 2005 Gorillaz album with the hit single "Feel Good Inc.": 2 wds. |
| 48% | DOJACAT | 7 | Singer whose 2021 hit single "Kiss Me More" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 48% | HEYYA | 5 | 2003 OutKast song: 2 wds. |
| 48% | WILDHORSES | 10 | Hit single from 31-Across with the lyric "we'll ride them someday": 2 wds. |
| 48% | JACKSONBROWNE | 13 | "Running on Empty" singer with the hit single "Somebody's Baby": 2 wds. |
| 48% | DIERKSBENTLEY | 13 | Country star with the 2016 hit single "Somewhere on a Beach": 2 wds. |
| 47% | SLUMBERPARTY | 12 | Hit single by Britney Spears (birthday today) from her ninth album, "Glory," featuring Tinashe: 2 wds. |
| 47% | HEYYA | 5 | Outkast hit single |
| 47% | LINDARONSTADT | 13 | "You're No Good" singer with the hit single "Ooh Baby Baby": 2 wds. |
| 47% | THATSALLRIGHT | 13 | Elvis Presley hit single whose B-side is "Blue Moon of Kentucky" (3 wds.) |
| 47% | THEDIXIECUPS | 12 | 1960s girl group trio who had the hit single "Chapel of Love" (3 wds.) |
| 46% | DUALIPA | 7 | Elton John's collaborator on the 2021 hit single "Cold Heart (Pnau Remix)": 2 wds. |
| 46% | ABOUTDAMNTIME | 13 | 2022 Lizzo hit single that won a Grammy for Record of the Year (3 wds.) |
| 46% | BLAKESHELTON | 12 | His "God's Country" won the 2019 CMA for Single of the Year: 2 wds. |
| 46% | MYEVERYTHING | 12 | 2014 album by 18-Across with the hit singles "Problem" and "Break Free": 2 wds. |