| 100% | ALWAYSONMYMIND | 14 | Album by 30-Across/33-Across that was the "Billboard" #1 country album of the year for 1982 (4 wds.) |
| 61% | ONTHEROADAGAIN | 14 | Song by 30-Across/33-Across that won a Grammy Award for Best Country Song and was inducted into the Grammy Hall of Fame (4 wds.) |
| 54% | BESTOFMYLOVE | 12 | Song by the Emotions that was #3 on Billboard's year-end Hot 100 for 1977: 4 wds. |
| 48% | KILLINTIME | 10 | Album by 45-Across featuring the singles 18-Across and 26-Across that won the 1989 Album of the Year Academy of Country Music Award (2 wds.) |
| 47% | MARENMORRIS | 11 | 1-Across, 12-Across, 27-Across, and 50-Across country/pop singer who was named Female Vocalist of the Year by the Country Music Association in 2020 (2 wds.) |
| 46% | CHASINYOU | 9 | Single on 15-Across that was the third consecutive #1 hit for 28-Across on the Billboard Country Airplay Chart (2 wds.) |
| 46% | THRILLER | 8 | Album by Michael Jackson and Quincy Jones that won the Grammy for Album of the Year in 1984 |
| 46% | HOTPINK | 7 | Album by 50-Across that was nominated for Favorite Soul/R&B Album at the 2020 American Music Awards (2 wds.) |
| 46% | ALLI | 4 | "___ Want For Christmas is You," song by Mariah Carey that topped the charts after 25 years of its release: 2 wds. |
| 46% | ROLLWITHIT | 10 | 1988 #1 hit for 30-Across, which was nominated for the Grammy for Record of the Year: 3 wds. |
| 46% | IFIKNOWME | 9 | Album by 28-Across that reached #1 on the Top Country Albums chart in 2020 (4 wds.) |
| 46% | NIGHTFALL | 9 | 2020 album by 33-Across that was nominated for a Best Country Album Grammy Award |
| 45% | GIRL | 4 | 2019 album by 44-Across that won the Country Music Association's Album of the Year Award |
| 45% | DREAM | 5 | "Teenage ___," third studio album by Katy Perry that was nominated for a Grammy for Album of the Year in 2011 |
| 45% | WALKLIKEAMAN | 12 | No. 1 song by 30-Across that's included in the Rock & Roll Hall of Fame's list of "Songs That Shaped Rock and Roll" (4 wds.) |
| 44% | MELODRAMA | 9 | 2017 album by 53-Across that received a Grammy Award nomination for Album of the Year |
| 44% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 44% | KILLINGFLOOR | 12 | Debut novel by 25-Across that was the basis for the first season of "Reacher" (2 wds.) |
| 44% | ABETTERMAN | 10 | #1 song by 45-Across from 35-Across that won the 1989 Single of the Year Academy of Country Music Award (3 wds.) |
| 44% | NEXT | 4 | "Thank U, ___," number-one hit album by Ariana Grande that was nominated for Album of the Year at the 62nd Grammy Awards |
| 44% | THEBOYISMINE | 12 | 1998 Brandy and Monica song that was #1 on the Billboard Hot 100 for 13 weeks: 4 wds. |
| 44% | JASONALDEAN | 11 | 17-Across and 30-Across country singer who was named ACM's Artist of the Decade for the 2010s (2 wds.) |
| 43% | OLIVIARODRIGO | 13 | "Good 4 U" singer who was Billboard's 2021 Woman of the Year: 2 wds. |
| 43% | BANGLADESH | 10 | 1971 charity single by George Harrison that was written to raise awareness for millions of refugees from the country in the title: 2 wds. |
| 43% | TAKINITBACK | 11 | Studio album by 30-Across that debuted at No. 16 on the "Billboard" 200 (3 wds.) |
| 43% | KACEYMUSGRAVES | 14 | 19-Across and 46-Across singer who won four 2019 Grammys, including Album of the Year and Best Country Album for "Golden Hour" (2 wds.) |
| 43% | OUTOFTHEWOODS | 13 | Hit single by 30-Across from the album "1989" that asks, "Are we in the clear yet?" (4 wds.) |
| 43% | THEWAYWEWERE | 12 | Barbra Streisand hit that was No. 1 on Billboard's Year-End Hot 100 Singles of 1974 (4 wds.) |
| 43% | ROBREINER | 9 | Director of 33-Across who will write a foreword for the book by 15-Across: 2 wds. |
| 42% | THEWAYIMLIVIN | 13 | Album by 29-Across/32-Across nominated for the Best Country Album Grammy Award in 2015 (4 wds.) |