| 100% | ANNAKENDRICK | 12 | Actress who had a song from "Pitch Perfect" chart on the Billboard Hot 100 in 2013: 2 wds. |
| 89% | ANNEHATHAWAY | 12 | Actress who had a song from "Les Misérables" chart on the Billboard Hot 100 in 2013: 2 wds. |
| 69% | BRADLEYCOOPER | 13 | Actor who had a song from "A Star Is Born" chart on the Billboard Hot 100 in 2018: 2 wds. |
| 57% | THEWEEKND | 9 | "Starboy" pop singer who had 18 songs on the Billboard Hot 100 during a week in 2016: 2 wds. |
| 53% | ARIANAGRANDE | 12 | "Yes, And?" singer who had two songs reach #1 on the Billboard Hot 100 in 2024: 2 wds. |
| 53% | KENDRICKLAMAR | 13 | "Humble" rapper who had 14 songs on the Hot 100 during a week in 2017: 2 wds. |
| 50% | EDSHEERAN | 9 | "Shape of You" pop singer who had 13 songs on the Hot 100 during a week in 2017: 2 wds. |
| 47% | WHATSNEXT | 9 | Drake song that hit #1 on the Billboard Hot 100 in 2021: 2 wds. |
| 47% | ALANJACKSON | 11 | Singer whose "Country Boy" hit #1 on the Billboard Hot Country Songs Chart in 2009: 2 wds. |
| 46% | MARIAHCAREY | 11 | "Honey" singer who's had three songs debut at #1 on the Billboard Hot 100: 2 wds. |
| 45% | LONDONBRIDGE | 12 | Fergie song that reached #1 on the Billboard Hot 100 in the summer of 2006: 2 wds. |
| 45% | MARIAHCAREY | 11 | Singer whose song "We Belong Together" peaked at number one on the Billboard Hot 100 chart in 2005: 2 wds. |
| 44% | KELLYCLARKSON | 13 | Singer whose debut single "A Moment Like This" reached #1 on the Billboard Hot 100 in 2002: 2 wds. |
| 44% | TAYLORSWIFT | 11 | "Shake It Off" singer who's had seven songs debut at #1 on the Billboard Hot 100: 2 wds. |
| 44% | NICKIMINAJ | 10 | Rapper whose song "Anaconda" peaked at #2 on the Billboard Hot 100 in August 2014: 2 wds. |
| 44% | RICKYMARTIN | 11 | Singer whose song "Livin' La Vida Loca" peaked at number one on the Billboard Hot 100 chart in 1999: 2 wds. |
| 44% | ARIANAGRANDE | 12 | "Thank U, Next" singer who's had seven songs debut at #1 on the Billboard Hot 100: 2 wds. |
| 43% | BLURREDLINES | 12 | 2013 Robin Thicke song that was #1 on the Billboard Hot 100 for 12 weeks: 2 wds. |
| 42% | OLIVIARODRIGO | 13 | Singer whose debut single "Drivers License" reached #1 on the Billboard Hot 100 in 2021: 2 wds. |
| 42% | 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. |
| 41% | DRAKE | 5 | "God's Plan" rapper who had 24 songs on the Hot 100 during a week in 2017 |
| 41% | MEGHANTRAINOR | 13 | Singer whose debut single "All About That Bass" reached #1 on the Billboard Hot 100 in 2014: 2 wds. |
| 41% | FAMILYAFFAIR | 12 | 28-Across song that spent six weeks at #1 on the Billboard Hot 100 in 2001 (2 wds.) |
| 41% | KIMPETRAS | 9 | First openly transgender woman to have a No. 1 song on the Billboard Hot 100 chart |
| 41% | TRACEADKINS | 11 | Singer whose "Ladies Love Country Boys" hit #1 on the Billboard Country Songs Chart in 2007: 2 wds. |
| 40% | UPSIDEDOWN | 10 | 1980 50-Across song that hit #1 on the Billboard Hot 100, Disco, and Soul charts (2 wds.) |
| 40% | LETITIAWRIGHT | 13 | Actress who plays Shuri in the Marvel Cinematic Universe and has been on "Black Mirror": 2 wds. |
| 40% | STEVIEWONDER | 12 | "Sir Duke" singer who debuted songs on the Hot 100 in five different decades: 2 wds. |
| 39% | HOTLINEBLING | 12 | 2015 Drake song that peaked at #2 on the Billboard Hot 100: 2 wds. |
| 39% | CHEAPTHRILLS | 12 | 2016 Sia song that reached #1 on the Billboard Hot 100: 2 wds. |