| 100% | RAYCHARLES | 10 | Soul singer whose posthumous album "Genius Loves Company" topped the charts in 2005: 2 wds. |
| 60% | DAVIDBOWIE | 10 | Rock singer whose posthumous album "Blackstar" topped the charts in 2016: 2 wds. |
| 49% | MICHAEL | 7 | With 33-Across, pop singer whose posthumous album "This Is It" topped the charts in 2009 |
| 47% | TAYLORSWIFT | 11 | Singer whose 2014 album "1989" had five songs top the Mainstream Top 40 chart: 2 wds. |
| 47% | SELENAGOMEZ | 11 | Singer whose 2015 album "Revival" had three songs top the Mainstream Top 40 chart: 2 wds. |
| 46% | AVRILLAVIGNE | 12 | Singer whose 2002 album "Let Go" had three songs top the Mainstream Top 40 chart: 2 wds. |
| 46% | STEVIEWONDER | 12 | Soul singer whose 1976 album "Songs in the Key of Life" spent its first 13 weeks atop the Billboard 200: 2 wds. |
| 46% | EDSHEERAN | 9 | English singer whose album "÷" and song "Shape of You" both topped the charts in 2017: 2 wds. |
| 44% | BRETTELDREDGE | 13 | Country singer whose "Baby, It's Cold Outside" topped the Adult Contemporary chart in 2017: 2 wds. |
| 44% | KANYEWEST | 9 | Rapper whose album "Graduation" and song "Stronger" both topped the charts in 2007: 2 wds. |
| 44% | KENDRICKLAMAR | 13 | Rapper whose album "Damn" and song "Humble" both topped the charts in 2017: 2 wds. |
| 44% | CHRISSTAPLETON | 14 | Country singer whose album "Traveller" topped the Billboard 200 in 2015: 2 wds. |
| 43% | ELVISPRESLEY | 12 | Musician whose self-titled album topped the charts in 1956 when he was just 21 years old: 2 wds. |
| 42% | TRACEADKINS | 11 | Singer whose "Ladies Love Country Boys" hit #1 on the Billboard Country Songs Chart in 2007: 2 wds. |
| 41% | JASONALDEAN | 11 | Country singer whose album "They Don't Know" topped the Billboard 200 in 2016: 2 wds. |
| 41% | ADELE | 5 | Singer whose second album, in 2011, topped the Billboard chart for a record 24 weeks |
| 41% | THOMASRHETT | 11 | Country singer whose album "Life Changes" topped the Billboard 200 in 2017: 2 wds. |
| 39% | PATTYLOVELESS | 13 | "Blame It on Your Heart" singer whose "Mountain Soul II" won the Best Bluegrass Album Grammy in 2011: 2 wds. |
| 38% | BEYONCEKNOWLES | 14 | Singer whose song "Crazy In Love" featuring Jay Z peaked at number one on the Billboard Hot 100 chart in 2003: 2 wds. |
| 37% | BLACKPANTHER | 12 | Superhero movie whose soundtrack topped the Billboard charts in 2018: 2 wds. |
| 37% | LESMISERABLES | 13 | Musical drama whose soundtrack topped the Billboard charts in 2013: 2 wds. |
| 37% | MEGHANTRAINOR | 13 | Singer whose "All About That Bass" spent 25 weeks in the Billboard Top 10 in 2014 and 2015: 2 wds. |
| 37% | LEANNRIMES | 10 | Singer whose "How Do I Live" spent 32 weeks in the Billboard Top 10 in 1997 and 1998: 2 wds. |
| 36% | SUICIDESQUAD | 12 | Comic book movie whose soundtrack topped the Billboard charts in 2016: 2 wds. |
| 36% | MARIAHCAREY | 11 | Singer whose song "We Belong Together" peaked at number one on the Billboard Hot 100 chart in 2005: 2 wds. |
| 36% | BRITNEYSPEARS | 13 | Singer whose "Oops! ... I Did It Again" album went platinum in one week: 2 wds. |
| 36% | BRUNOMARS | 9 | Singer whose second album, "Unorthodox Jukebox," came out in December 2012: 2 wds. |
| 36% | NORAHJONES | 10 | Singer whose "Feels Like Home" album went platinum in one week: 2 wds. |
| 35% | MORGANWALLEN | 12 | "7 Summers" country singer whose "You Proof" hit the Billboard Top 10 in 2022: 2 wds. |
| 35% | LUKECOMBS | 9 | "Forever After All" country singer whose "The Kind of Love We Make" hit the Billboard Top 10 in 2022: 2 wds. |