| 100% | JASONALDEAN | 11 | Country singer whose album "They Don't Know" topped the Billboard 200 in 2016: 2 wds. |
| 65% | CHRISSTAPLETON | 14 | Country singer whose album "Traveller" topped the Billboard 200 in 2015: 2 wds. |
| 64% | THOMASRHETT | 11 | Country singer whose album "Life Changes" topped the Billboard 200 in 2017: 2 wds. |
| 53% | MORGANWALLEN | 12 | "7 Summers" country singer whose "You Proof" hit the Billboard Top 10 in 2022: 2 wds. |
| 52% | MORGANWALLEN | 12 | Country singer whose 2021 double album "Dangerous" spent its first 10 weeks atop the Billboard 200: 2 wds. |
| 52% | ZACHBRYAN | 9 | "Heading South" country singer whose "Something in the Orange" hit the Billboard Top 10 in 2023: 2 wds. |
| 51% | LUKECOMBS | 9 | "Forever After All" country singer whose "The Kind of Love We Make" hit the Billboard Top 10 in 2022: 2 wds. |
| 50% | DAVIDBOWIE | 10 | Rock singer whose posthumous album "Blackstar" topped the charts in 2016: 2 wds. |
| 47% | SUICIDESQUAD | 12 | Comic book movie whose soundtrack topped the Billboard charts in 2016: 2 wds. |
| 46% | EDSHEERAN | 9 | English singer whose album "÷" and song "Shape of You" both topped the charts in 2017: 2 wds. |
| 46% | BRETTELDREDGE | 13 | Country singer whose "Baby, It's Cold Outside" topped the Adult Contemporary chart in 2017: 2 wds. |
| 44% | MEGHANTRAINOR | 13 | Singer whose "All About That Bass" spent 25 weeks in the Billboard Top 10 in 2014 and 2015: 2 wds. |
| 44% | LEANNRIMES | 10 | Singer whose "How Do I Live" spent 32 weeks in the Billboard Top 10 in 1997 and 1998: 2 wds. |
| 43% | CAMILACABELLO | 13 | "Havana" singer who simultaneously topped the Billboard 200, Hot 100, and Artist 100 in 2018: 2 wds. |
| 43% | FAITHHILL | 9 | Country singer whose song "Breathe" was named the #1 single on Billboard's year-end countdown in 2000 (2 wds.) |
| 43% | MIRANDALAMBERT | 14 | Singer whose "Wildcard" won the Grammy for Best Country Album in 2021: 2 wds. |
| 42% | CHRISSTAPLETON | 14 | Singer whose "Starting Over" won the Grammy for Best Country Album in 2022: 2 wds. |
| 42% | KENDRICKLAMAR | 13 | "Humble" rapper who simultaneously topped the Billboard 200, Hot 100, and Artist 100 in 2017: 2 wds. |
| 42% | DOLLYPARTON | 11 | Country singer whose latest album, "I Believe In You," is geared toward children: 2 wds. |
| 40% | BLACKPANTHER | 12 | Superhero movie whose soundtrack topped the Billboard charts in 2018: 2 wds. |
| 40% | LESMISERABLES | 13 | Musical drama whose soundtrack topped the Billboard charts in 2013: 2 wds. |
| 40% | TRACEADKINS | 11 | Singer whose "Ladies Love Country Boys" hit #1 on the Billboard Country Songs Chart in 2007: 2 wds. |
| 39% | ALANJACKSON | 11 | Singer whose "Country Boy" hit #1 on the Billboard Hot Country Songs Chart in 2009: 2 wds. |
| 39% | AVRILLAVIGNE | 12 | Singer whose 2002 album "Let Go" had three songs top the Mainstream Top 40 chart: 2 wds. |
| 39% | ANDREABOCELLI | 13 | Italian classical singer whose album "Cinema" was nominated for Best Traditional Pop Vocal Album in the 2017 Grammy Awards : 2 wds. |
| 39% | BRETTELDREDGE | 13 | "Somethin' I'm Good At" singer who topped the Billboard Country Albums chart with his latest LP: 2 wds. |
| 39% | RAYCHARLES | 10 | Soul singer whose posthumous album "Genius Loves Company" topped the charts in 2005: 2 wds. |
| 38% | TAYLORSWIFT | 11 | Singer whose 2014 album "1989" had five songs top the Mainstream Top 40 chart: 2 wds. |
| 38% | SELENAGOMEZ | 11 | Singer whose 2015 album "Revival" had three songs top the Mainstream Top 40 chart: 2 wds. |
| 38% | SHANIATWAIN | 11 | "That Don't Impress Me Much" singer who received the Billboard Women in Music Icon Award in 2016: 2 wds. |