| 100% | KENDRICKLAMAR | 13 | "Squabble Up" rapper who had three songs reach #1 in 2024: 2 wds. |
| 65% | MORGANWALLEN | 12 | "Love Somebody" singer who had two songs reach #1 in 2024: 2 wds. |
| 57% | ARIANAGRANDE | 12 | "Yes, And?" singer who had two songs reach #1 on the Billboard Hot 100 in 2024: 2 wds. |
| 48% | KENDRICKLAMAR | 13 | "Humble" rapper who had 14 songs on the Hot 100 during a week in 2017: 2 wds. |
| 47% | LILWAYNE | 8 | "A Milli" rapper who's had top 10 hits in each of the last three decades: 2 wds. |
| 43% | WYCLEFJEAN | 10 | "Gone Till November" rapper who has lived in both Haiti and the US: 2 wds. |
| 42% | FOXYBROWN | 9 | "I'll Be" rapper who has been a pioneer for women in hip-hop: 2 wds. |
| 41% | MARIAHCAREY | 11 | "Honey" singer who's had three songs debut at #1 on the Billboard Hot 100: 2 wds. |
| 41% | FLORIDA | 7 | Rapper who had a top 10 hit in 2015 with "G.D.F.R.": 2 wds. |
| 39% | ANNAKENDRICK | 12 | Actress who had a song from "Pitch Perfect" chart on the Billboard Hot 100 in 2013: 2 wds. |
| 39% | ANNEHATHAWAY | 12 | Actress who had a song from "Les Misérables" chart on the Billboard Hot 100 in 2013: 2 wds. |
| 39% | MOSDEF | 6 | Rapper who had a recurring role on "Dexter": 2 wds. |
| 38% | BRADLEYCOOPER | 13 | Actor who had a song from "A Star Is Born" chart on the Billboard Hot 100 in 2018: 2 wds. |
| 38% | IGGYAZALEA | 10 | "Fancy" rapper featured on three songs in Billboard's top 10 during a week in 2014: 2 wds. |
| 38% | DRDRE | 5 | Rapper who appeared in "Training Day": 2 wds. |
| 38% | KENDRICKLAMAR | 13 | Rapper who duetted with SZA on 2024's "Luther," a #1 hit for 13 weeks: 2 wds. |
| 37% | THEBEEGEES | 10 | Brothers Barry, Maurice, and Robin who had nine #1 songs in the 1970s (3 wds.) |
| 37% | ANGELINAJOLIE | 13 | "A Mighty Heart" actress who has three adopted children: 2 wds. |
| 36% | THEWEEKND | 9 | "Starboy" pop singer who had 18 songs on the Billboard Hot 100 during a week in 2016: 2 wds. |
| 36% | FETTYWAP | 8 | "Trap Queen" rapper who released a self-titled #1 album in 2015: 2 wds. |
| 35% | NICKIMINAJ | 10 | "Anaconda" singer who has lived in both Trinidad and the US: 2 wds. |
| 35% | VITOCORLEONE | 12 | Character who has the title role in 15-Across: 2 wds. |
| 35% | GERIHALLIWELL | 13 | Singer who had four #1 hits in the UK from 1999 to 2001, including "It's Raining Men": 2 wds. |
| 35% | SELENAGOMEZ | 11 | Singer whose 2015 album "Revival" had three songs top the Mainstream Top 40 chart: 2 wds. |
| 35% | ROBERTOLUONGO | 13 | NHL goalie who had his number 1 retired by the Florida Panthers in 2020: 2 wds. |
| 35% | JACQUESPLANTE | 13 | NHL goalie who had his number 1 retired by the Montreal Canadiens in 1995: 2 wds. |
| 35% | JOHNMCCAIN | 10 | Former Arizona senator who had a cameo in "Wedding Crashers": 2 wds. |
| 35% | STPAT | 5 | Irish figure who has a holiday in March, for short: 2 wds. |
| 35% | AVRILLAVIGNE | 12 | Singer whose 2002 album "Let Go" had three songs top the Mainstream Top 40 chart: 2 wds. |
| 35% | SHAGGY | 6 | Rapper who made up the word "boombastic" in a 1995 song of the same name |