| 100% | JONASBROTHERS | 13 | Pop trio whose "Like It's Christmas" topped the Adult Contemporary chart in 2019: 2 wds. |
| 60% | BRETTELDREDGE | 13 | Country singer whose "Baby, It's Cold Outside" topped the Adult Contemporary chart in 2017: 2 wds. |
| 53% | KELLYCLARKSON | 13 | "American Idol" winner whose "Underneath the Tree" topped the Adult Contemporary chart in 2013: 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. |
| 36% | DAVIDBOWIE | 10 | Rock singer whose posthumous album "Blackstar" topped the charts in 2016: 2 wds. |
| 36% | SUICIDESQUAD | 12 | Comic book movie whose soundtrack topped the Billboard charts in 2016: 2 wds. |
| 35% | MICHAEL | 7 | With 33-Across, pop singer whose posthumous album "This Is It" topped the charts in 2009 |
| 33% | ELVISPRESLEY | 12 | Musician whose self-titled album topped the charts in 1956 when he was just 21 years old: 2 wds. |
| 33% | RAYCHARLES | 10 | Soul singer whose posthumous album "Genius Loves Company" topped the charts in 2005: 2 wds. |
| 33% | JUSTINBIEBER | 12 | Pop/R&B singer who's also topped the Country chart, thanks to "10,000 Hours" with Dan + Shay: 2 wds. |
| 33% | KANYEWEST | 9 | Rapper whose album "Graduation" and song "Stronger" both topped the charts in 2007: 2 wds. |
| 33% | KENDRICKLAMAR | 13 | Rapper whose album "Damn" and song "Humble" both topped the charts in 2017: 2 wds. |
| 33% | LITTLEEVA | 9 | Pop singer whose version of "The Loco-Motion" inspired a dance craze in the 1960s: 2 wds. |
| 32% | MICHAELJACKSON | 14 | Pop singer whose hologram performed at the Billboard Music Awards in 2014: 2 wds. |
| 32% | JACKLEMMON | 10 | "Some Like It Hot" actor who starred in "The Odd Couple": 2 wds. |
| 31% | HARRYSTYLES | 11 | Singer whose "As It Was" won the MTV Video Music Award for Best Pop Video in 2022: 2 wds. |
| 31% | MARRYME | 7 | Song from Thomas Rhett's "Life Changes" album that topped the Country Airplay charts in 2018: 2 wds. |
| 31% | ICEHOCKEY | 9 | Popular winter sport whose origin may be disputed but the game in its contemporary form was first played in Montreal, Canada: 2 wds. |
| 30% | MARILYNMONROE | 13 | "Some Like It Hot" actress whose last film role was Roslyn Tabor in 44-Across (2 wds.) |
| 30% | BADGUY | 6 | Billie Eilish song that topped the charts: 2 wds. |
| 30% | EDSHEERAN | 9 | English singer whose album "÷" and song "Shape of You" both topped the charts in 2017: 2 wds. |
| 29% | THEBEEGEES | 10 | Pop trio with the most #1 Billboard Hot 100 hits (9) during the 1970s: 2 wds. |
| 29% | DIRTYDANCING | 12 | 1987 Patrick Swayze movie whose soundtrack topped the charts for 18 weeks: 2 wds. |
| 29% | THEBODYGUARD | 12 | 1992 Whitney Houston film whose soundtrack topped the charts for 20 weeks: 2 wds. |
| 29% | MARILYNMONROE | 13 | American actress from the '50s who starred in "Some Like It Hot": 2 wds. |
| 29% | BRITNEYSPEARS | 13 | Musician whose first single "... Baby one more time" topped the charts in 1998 when she was just 17 years old: 2 wds. |
| 29% | SNOOPDOGG | 9 | Rapper with the 2004 #1 hit "Drop It Like It's Hot" whose name contains an unexpected double letter: 2 wds. |
| 29% | ICECUBE | 7 | It's a "rock" in "on the rocks": 2 wds. |
| 29% | THOMASRHETT | 11 | Country singer whose album "Life Changes" topped the Billboard 200 in 2017: 2 wds. |