| 100% | DAVIDBOWIE | 10 | Rock singer whose posthumous album "Blackstar" topped the charts in 2016: 2 wds. |
| 68% | RAYCHARLES | 10 | Soul singer whose posthumous album "Genius Loves Company" topped the charts in 2005: 2 wds. |
| 57% | MICHAEL | 7 | With 33-Across, pop singer whose posthumous album "This Is It" topped the charts in 2009 |
| 56% | JASONALDEAN | 11 | Country singer whose album "They Don't Know" topped the Billboard 200 in 2016: 2 wds. |
| 54% | TAYLORSWIFT | 11 | Singer whose 2014 album "1989" had five songs top the Mainstream Top 40 chart: 2 wds. |
| 54% | SELENAGOMEZ | 11 | Singer whose 2015 album "Revival" had three songs top the Mainstream Top 40 chart: 2 wds. |
| 54% | CHRISSTAPLETON | 14 | Country singer whose album "Traveller" topped the Billboard 200 in 2015: 2 wds. |
| 54% | AVRILLAVIGNE | 12 | Singer whose 2002 album "Let Go" had three songs top the Mainstream Top 40 chart: 2 wds. |
| 53% | EDSHEERAN | 9 | English singer whose album "÷" and song "Shape of You" both topped the charts in 2017: 2 wds. |
| 51% | SUICIDESQUAD | 12 | Comic book movie whose soundtrack topped the Billboard charts in 2016: 2 wds. |
| 50% | KANYEWEST | 9 | Rapper whose album "Graduation" and song "Stronger" both topped the charts in 2007: 2 wds. |
| 50% | KENDRICKLAMAR | 13 | Rapper whose album "Damn" and song "Humble" both topped the charts in 2017: 2 wds. |
| 50% | THOMASRHETT | 11 | Country singer whose album "Life Changes" topped the Billboard 200 in 2017: 2 wds. |
| 49% | ELVISPRESLEY | 12 | Musician whose self-titled album topped the charts in 1956 when he was just 21 years old: 2 wds. |
| 49% | CHUBBYCHECKER | 13 | Rock singer whose version of "The Twist" inspired a dance craze in the 1960s: 2 wds. |
| 48% | BRETTELDREDGE | 13 | Country singer whose "Baby, It's Cold Outside" topped the Adult Contemporary chart in 2017: 2 wds. |
| 47% | ADELE | 5 | Singer whose second album, in 2011, topped the Billboard chart for a record 24 weeks |
| 45% | MEGHANTRAINOR | 13 | Singer whose "All About That Bass" spent 25 weeks in the Billboard Top 10 in 2014 and 2015: 2 wds. |
| 45% | LEANNRIMES | 10 | Singer whose "How Do I Live" spent 32 weeks in the Billboard Top 10 in 1997 and 1998: 2 wds. |
| 43% | MIRANDALAMBERT | 14 | Singer whose "Wildcard" won the Grammy for Best Country Album in 2021: 2 wds. |
| 43% | BLACKPANTHER | 12 | Superhero movie whose soundtrack topped the Billboard charts in 2018: 2 wds. |
| 43% | LESMISERABLES | 13 | Musical drama whose soundtrack topped the Billboard charts in 2013: 2 wds. |
| 43% | STEVIEWONDER | 12 | Soul singer whose 1976 album "Songs in the Key of Life" spent its first 13 weeks atop the Billboard 200: 2 wds. |
| 42% | ALANJACKSON | 11 | Singer whose "Country Boy" hit #1 on the Billboard Hot Country Songs Chart in 2009: 2 wds. |
| 42% | NORAHJONES | 10 | Singer whose "Feels Like Home" album went platinum in one week: 2 wds. |
| 42% | BILLYJOEL | 9 | Singer whose 1980 "Glass Houses" album includes the #1 song "It's Still Rock and Roll to Me" (2 wds.) |
| 41% | TRACEADKINS | 11 | Singer whose "Ladies Love Country Boys" hit #1 on the Billboard Country Songs Chart in 2007: 2 wds. |
| 41% | CHRISSTAPLETON | 14 | Singer whose "Starting Over" won the Grammy for Best Country Album in 2022: 2 wds. |
| 41% | GERRYRAFFERTY | 13 | Yacht rock singer whose hits include "Baker Street" and "Right Down the Line": 2 wds. |
| 41% | BRUNOMARS | 9 | Singer whose second album, "Unorthodox Jukebox," came out in December 2012: 2 wds. |