| 100% | MICHAEL | 7 | With 33-Across, pop singer whose posthumous album "This Is It" topped the charts in 2009 |
| 50% | RAYCHARLES | 10 | Soul singer whose posthumous album "Genius Loves Company" topped the charts in 2005: 2 wds. |
| 49% | DAVIDBOWIE | 10 | Rock singer whose posthumous album "Blackstar" topped the charts in 2016: 2 wds. |
| 41% | ADELE | 5 | Singer whose second album, in 2011, topped the Billboard chart for a record 24 weeks |
| 39% | HARRYSTYLES | 11 | Singer whose "As It Was" won the MTV Video Music Award for Best Pop Video in 2022: 2 wds. |
| 39% | BRETTELDREDGE | 13 | Country singer whose "Baby, It's Cold Outside" topped the Adult Contemporary chart in 2017: 2 wds. |
| 39% | JONASBROTHERS | 13 | Pop trio whose "Like It's Christmas" topped the Adult Contemporary chart in 2019: 2 wds. |
| 39% | MILEY | 5 | With 33-Across, singer whose "Flowers" was the best-selling global single of 2023 |
| 38% | WILLIE | 6 | With 33-Across, country singer whose 1992 album "The IRS Tapes" was released to help pay his tax debts |
| 38% | ANDREABOCELLI | 13 | Italian classical singer whose album "Cinema" was nominated for Best Traditional Pop Vocal Album in the 2017 Grammy Awards : 2 wds. |
| 38% | OTISREDDING | 11 | US singer-songwriter whose posthumous album The Dock of the Bay was released in 1968 |
| 36% | ELVISPRESLEY | 12 | Musician whose self-titled album topped the charts in 1956 when he was just 21 years old: 2 wds. |
| 35% | JUSTIN | 6 | With 35-Across, "Yummy" singer who won the Pop Album of the Year Juno in 2011 and 2016 |
| 35% | CHRISSTAPLETON | 14 | Country singer whose album "Traveller" topped the Billboard 200 in 2015: 2 wds. |
| 34% | TAYLORSWIFT | 11 | Singer whose 2014 album "1989" had five songs top the Mainstream Top 40 chart: 2 wds. |
| 34% | SELENAGOMEZ | 11 | Singer whose 2015 album "Revival" had three songs top the Mainstream Top 40 chart: 2 wds. |
| 34% | AVRILLAVIGNE | 12 | Singer whose 2002 album "Let Go" had three songs top the Mainstream Top 40 chart: 2 wds. |
| 34% | MICHAEL | 7 | With 33-Across, King of Pop whose estate was called Neverland |
| 34% | THESEEDSOFLOVE | 14 | 1989 studio album by 42-Across whose opening track is the Top 40 hit single "Woman in Chains" (4 wds.) |
| 34% | WILLIE | 6 | With 39-Across, singer whose "A Beautiful Time" won the Grammy for Best Country Album in 2023 |
| 34% | JASONALDEAN | 11 | Country singer whose album "They Don't Know" topped the Billboard 200 in 2016: 2 wds. |
| 33% | JONBATISTE | 10 | Singer whose album "We Are" won the Album of the Year Grammy in 2022 |
| 33% | KEEPTHEFAITH | 12 | 1992 Bon Jovi album whose three Top 40 hits were the title track, "Bed of Roses," and "In These Arms" (3 wds.) |
| 33% | LEANN | 5 | With 33-Across, "Blue" singer who won the Best New Artist Grammy in 1997 |
| 33% | CARYELWES | 9 | Star of 33-Across whose memoir about it, "As You Wish," will be published in the fall of 2014: 2 wds. |
| 32% | DOLLYPARTON | 11 | "Jolene" singer whose 2021 Scent from Above perfume sold out in the first week it was available (2 wds.) |
| 32% | THOMASRHETT | 11 | Country singer whose album "Life Changes" topped the Billboard 200 in 2017: 2 wds. |
| 32% | EDSHEERAN | 9 | English singer whose album "÷" and song "Shape of You" both topped the charts in 2017: 2 wds. |
| 32% | JUSTIN | 6 | With 33-Across, pop idol who was the Best New Artist at the 2010 MTV Video Music Awards |
| 32% | JLO | 3 | Singer whose "This Is Me ... Now" album dropped in 2024, for short: 2 wds. |