| 100% | MARIAHCAREY | 11 | "Fantasy" singer who recently became the first person to top the Billboard Hot 100 in four different decades: 2 wds. |
| 63% | MANNYPACQUIAO | 13 | Filipino boxer who recently became the first person to hold a world title in four different decades: 2 wds. |
| 56% | VINCECARTER | 11 | Atlanta Hawks forward who recently became the first to play in the NBA in four different decades: 2 wds. |
| 50% | LASTNIGHT | 9 | 2023 Morgan Wallen hit that became his first song to top the Billboard Hot 100: 2 wds. |
| 45% | CAMILACABELLO | 13 | "Havana" singer who simultaneously topped the Billboard 200, Hot 100, and Artist 100 in 2018: 2 wds. |
| 43% | STEVIEWONDER | 12 | "Sir Duke" singer who debuted songs on the Hot 100 in five different decades: 2 wds. |
| 42% | RICHARDBYRD | 11 | American explorer who in 1929 became the first person to fly over the South Pole: 2 wds. |
| 42% | ROALDAMUNDSEN | 13 | Norwegian explorer who in 1911 became the first person to reach the South Pole, one month ahead of 18-Across: 2 wds. |
| 40% | KATYPERRY | 9 | Starting in 2010, pop singer with a song in the top 10 of the Billboard Hot 100 for 69 consecutive weeks: 2 wds. |
| 40% | KENDRICKLAMAR | 13 | "Humble" rapper who simultaneously topped the Billboard 200, Hot 100, and Artist 100 in 2017: 2 wds. |
| 39% | THEWEEKND | 9 | "Starboy" pop singer who had 18 songs on the Billboard Hot 100 during a week in 2016: 2 wds. |
| 38% | OLIVIARODRIGO | 13 | Singer whose debut single "Drivers License" reached #1 on the Billboard Hot 100 in 2021: 2 wds. |
| 38% | ARIANAGRANDE | 12 | "Yes, And?" singer who had two songs reach #1 on the Billboard Hot 100 in 2024: 2 wds. |
| 38% | MARIAHCAREY | 11 | Singer whose song "We Belong Together" peaked at number one on the Billboard Hot 100 chart in 2005: 2 wds. |
| 38% | IGGYAZALEA | 10 | "Fancy" singer featured on "Problem" who in 2014 became the second ever to be simultaneously #1 and #2 with her first two hits: 2 wds. |
| 37% | KELLYCLARKSON | 13 | Singer whose debut single "A Moment Like This" reached #1 on the Billboard Hot 100 in 2002: 2 wds. |
| 37% | MEGHANTRAINOR | 13 | Singer whose debut single "All About That Bass" reached #1 on the Billboard Hot 100 in 2014: 2 wds. |
| 37% | BRADLEYCOOPER | 13 | Actor who had a song from "A Star Is Born" chart on the Billboard Hot 100 in 2018: 2 wds. |
| 37% | ANNAKENDRICK | 12 | Actress who had a song from "Pitch Perfect" chart on the Billboard Hot 100 in 2013: 2 wds. |
| 37% | ANNEHATHAWAY | 12 | Actress who had a song from "Les Misérables" chart on the Billboard Hot 100 in 2013: 2 wds. |
| 37% | RICKYMARTIN | 11 | Singer whose song "Livin' La Vida Loca" peaked at number one on the Billboard Hot 100 chart in 1999: 2 wds. |
| 37% | ADELE | 5 | First solo female singer with three songs in the top 10 of the Billboard Hot 100 simultaneously |
| 36% | PHYSICALSALES | 13 | Billboard Hot 100 ranking factor that relates to albums bought in person: 2 wds. |
| 36% | 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. |
| 36% | ICEICEBABY | 10 | First hip-hop single to top the Billboard Hot 100 (1990) |
| 35% | JOHNSALLEY | 10 | First NBA player to win a championship in three different decades and who is also a vegan activist: 2 wds. |
| 35% | RODSTEWART | 10 | Singer who performed his song "Infatuation" to open the first MTV Video Music Awards, in 1984: 2 wds. |
| 35% | ADELE | 5 | "Hello" singer who simultaneously topped the Billboard 200, Hot 100, and Artist 100 in 2015 and 2016 |
| 35% | MADONNA | 7 | "Vogue" singer who debuted songs on the Hot 100 in five different decades |
| 35% | RAMIMALEK | 9 | Actor who became the first one of Egyptian heritage to win an Oscar for Best Actor in 2019: 2 wds. |