| 100% | MARRYME | 7 | Song from Thomas Rhett's "Life Changes" album that topped the Country Airplay charts in 2018: 2 wds. |
| 81% | UNFORGETTABLE | 13 | Song from Thomas Rhett's "Life Changes" album that topped the Country Airplay charts in 2017 |
| 81% | SIXTEEN | 7 | Song from Thomas Rhett's "Life Changes" album that topped the Country Airplay charts in 2019 |
| 41% | LETTERTOME | 10 | Song from the album "5th Gear" that was Brad Paisley's sixth consecutive #1 hit on the "Billboard" Hot Country Songs chart (3 wds.) |
| 40% | HEARTBREAKER | 12 | 1978 Dolly Parton song from the eponymous album that topped the U.S. country singles chart |
| 38% | THOMASRHETT | 11 | Country singer whose album "Life Changes" topped the Billboard 200 in 2017: 2 wds. |
| 38% | MUDONTHETIRES | 13 | Studio album that was #1 on the "Billboard" Top Country Albums chart and whose title track was Brad Paisley's fourth #1 hit on the "Billboard" Hot Country Songs chart (4 wds.) |
| 35% | BADGUY | 6 | Billie Eilish song that topped the charts: 2 wds. |
| 35% | WHENDOVESCRY | 12 | Song from the album 28-Across that was the top-selling single of 1984 (3 wds.) |
| 35% | SEVENWONDERS | 12 | "Odd" song from Fleetwood Mac's "Tango in the Night" album (2 wds.) |
| 34% | KANYEWEST | 9 | Rapper whose album "Graduation" and song "Stronger" both topped the charts in 2007: 2 wds. |
| 34% | KENDRICKLAMAR | 13 | Rapper whose album "Damn" and song "Humble" both topped the charts in 2017: 2 wds. |
| 34% | BRETTELDREDGE | 13 | "Somethin' I'm Good At" singer who topped the Billboard Country Albums chart with his latest LP: 2 wds. |
| 34% | SOMETHINGLIKE | 13 | "___ That", song from Tim McGraw about falling in love at 17, that was the top-played radio single in any musical genre in the 2000s: 2 wds. |
| 34% | STARTABAND | 10 | Song with Keith Urban from the album "Play" that was Brad Paisley's ninth consecutive #1 hit on the "Billboard" Hot Country Songs chart (3 wds.) |
| 33% | BLAMEITONYOU | 12 | Single from "9" by 40-Across that reached #1 on the U.S. Country Airplay charts in 2020 (4 wds.) |
| 33% | GOTWHATIGOT | 11 | Single from "9" by 40-Across that reached #1 on the U.S. Country Airplay charts in 2020 (4 wds.) |
| 33% | SPACECOWBOY | 11 | Single from the album "Golden Hour" that won Best Country Song at the 2019 Grammys: 2 wds. |
| 33% | BRETTELDREDGE | 13 | Country singer whose "Baby, It's Cold Outside" topped the Adult Contemporary chart in 2017: 2 wds. |
| 33% | ONENUMBERAWAY | 13 | 2018 song by 52-Across that reached #1 on the Billboard Country Airplay chart (3 wds.) |
| 33% | BLACKPANTHER | 12 | Superhero movie whose soundtrack topped the Billboard charts in 2018: 2 wds. |
| 33% | CHRISSTAPLETON | 14 | Country singer whose album "Traveller" topped the Billboard 200 in 2015: 2 wds. |
| 33% | SEXYSADIE | 9 | Girl in a Beatles song from the "White Album": 2 wds. |
| 33% | DUELINGBANJOS | 13 | Instrumental song from the movie "Deliverance" that hit #2 in 1973: 2 wds. |
| 32% | BROKENHALOS | 11 | Chris Stapleton single that won the 2018 Grammy for Best Country Song: 2 wds. |
| 32% | ROCKETMAN | 9 | Top 10 song from the 47-Across album "Honky Château" (2 wds.) |
| 31% | TEENAGEFEVER | 12 | Song from Drake's 2017 playlist, "More Life", that samples Jennifer Lopez's "If You Had My Love": 2 wds. |
| 31% | EDSHEERAN | 9 | English singer whose album "÷" and song "Shape of You" both topped the charts in 2017: 2 wds. |
| 31% | ANNAKENDRICK | 12 | Actress who had a song from "Pitch Perfect" chart on the Billboard Hot 100 in 2013: 2 wds. |
| 31% | ANNEHATHAWAY | 12 | Actress who had a song from "Les Misérables" chart on the Billboard Hot 100 in 2013: 2 wds. |