| 100% | KANYEWEST | 9 | Rapper whose album "Graduation" and song "Stronger" both topped the charts in 2007: 2 wds. |
| 82% | KENDRICKLAMAR | 13 | Rapper whose album "Damn" and song "Humble" both topped the charts in 2017: 2 wds. |
| 64% | EDSHEERAN | 9 | English singer whose album "÷" and song "Shape of You" both topped the charts in 2017: 2 wds. |
| 49% | DAVIDBOWIE | 10 | Rock singer whose posthumous album "Blackstar" topped the charts in 2016: 2 wds. |
| 47% | RAYCHARLES | 10 | Soul singer whose posthumous album "Genius Loves Company" topped the charts in 2005: 2 wds. |
| 46% | ELVISPRESLEY | 12 | Musician whose self-titled album topped the charts in 1956 when he was just 21 years old: 2 wds. |
| 43% | NICKIMINAJ | 10 | Rapper whose song "Anaconda" peaked at #2 on the Billboard Hot 100 in August 2014: 2 wds. |
| 42% | 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.) |
| 42% | TAYLORSWIFT | 11 | Singer whose 2014 album "1989" had five songs top the Mainstream Top 40 chart: 2 wds. |
| 42% | SELENAGOMEZ | 11 | Singer whose 2015 album "Revival" had three songs top the Mainstream Top 40 chart: 2 wds. |
| 40% | MARRYME | 7 | Song from Thomas Rhett's "Life Changes" album that topped the Country Airplay charts in 2018: 2 wds. |
| 40% | AVRILLAVIGNE | 12 | Singer whose 2002 album "Let Go" had three songs top the Mainstream Top 40 chart: 2 wds. |
| 40% | CHRISSTAPLETON | 14 | Country singer whose album "Traveller" topped the Billboard 200 in 2015: 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% | THOMASRHETT | 11 | Country singer whose album "Life Changes" topped the Billboard 200 in 2017: 2 wds. |
| 39% | SUICIDESQUAD | 12 | Comic book movie whose soundtrack topped the Billboard charts in 2016: 2 wds. |
| 39% | LIMPBIZKIT | 10 | Band whose "Chocolate Starfish and the Hot Dog Flavored Water" album went platinum in one week: 2 wds. |
| 37% | KENDRICKLAMAR | 13 | "Humble" rapper whose 2022 album generated four simultaneous top 10 hits: 2 wds. |
| 37% | NAS | 3 | Rapper who released the albums "Magic 2" and "Magic 3" in 2023 |
| 36% | BADGUY | 6 | Billie Eilish song that topped the charts: 2 wds. |
| 36% | JASONALDEAN | 11 | Country singer whose album "They Don't Know" topped the Billboard 200 in 2016: 2 wds. |
| 36% | BRITNEYSPEARS | 13 | Musician whose first single "... Baby one more time" topped the charts in 1998 when she was just 17 years old: 2 wds. |
| 36% | KEEPTHEFAITH | 12 | 1992 Bon Jovi album whose three Top 40 hits were the title track, "Bed of Roses," and "In These Arms" (3 wds.) |
| 36% | JONASBROTHERS | 13 | Pop trio whose "Like It's Christmas" topped the Adult Contemporary chart in 2019: 2 wds. |
| 35% | BRETTELDREDGE | 13 | "Somethin' I'm Good At" singer who topped the Billboard Country Albums chart with his latest LP: 2 wds. |
| 35% | KELLYCLARKSON | 13 | "American Idol" winner whose "Underneath the Tree" topped the Adult Contemporary chart in 2013: 2 wds. |
| 35% | KENDRICKLAMAR | 13 | "Humble" rapper who simultaneously topped the Billboard 200, Hot 100, and Artist 100 in 2017: 2 wds. |
| 34% | NELLY | 5 | Rapper whose songs "Hot in Herre" and "Dilemma" were simultaneously #1 and #2 in 2002 |