| 100% | DADDYYANKEE | 11 | Rapper/singer who duetted with Luis Fonsi on 2017's "Despacito," a #1 hit for 16 weeks: 2 wds. |
| 60% | MARIAHCAREY | 11 | Singer who duetted with Boyz II Men on 1995's "One Sweet Day," a #1 hit for 16 weeks: 2 wds. |
| 58% | KENDRICKLAMAR | 13 | Rapper who duetted with SZA on 2024's "Luther," a #1 hit for 13 weeks: 2 wds. |
| 49% | TOBYKEITH | 9 | Singer who duetted with Willie Nelson on the 2003 #1 country hit "Beer for My Horses": 2 wds. |
| 48% | EDSHEERAN | 9 | Singer who collaborated with Beyoncé on the 2017 #1 hit "Perfect Duet": 2 wds. |
| 40% | LUISFONSI | 9 | Singer who hit #1 in 2017 with the Spanish/English-language "Despacito": 2 wds. |
| 39% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 38% | BILLYPRESTON | 12 | Singer who sang with Nat King Cole on a TV show at 11 and released his first album at 16: 2 wds. |
| 38% | EDSHEERAN | 9 | "Shape of You" pop singer who had 13 songs on the Hot 100 during a week in 2017: 2 wds. |
| 37% | JIMMIEALLEN | 11 | "Best Shot" singer who collaborated with Brad Paisley on the 2021 country hit "Freedom Was a Highway": 2 wds. |
| 37% | GWENSTEFANI | 11 | Singer who dueted with her beau Blake Shelton on "You Make It Feel Like Christmas": 2 wds. |
| 37% | ADAMLEVINE | 10 | Maroon 5 singer who was a coach for 16 seasons on "The Voice" (2 wds.) |
| 36% | ARIANAGRANDE | 12 | "Thank U, Next" pop singer who got her seventh #1 hit with a remix of 38-Across: 2 wds. |
| 36% | LEEGREENWOOD | 12 | "I.O.U." singer who had a hit in 2001 with "God Bless the U.S.A.": 2 wds. |
| 36% | KATYPERRY | 9 | Singer who collaborated with Snoop Dogg on the 2010 No. 1 Billboard hit "California Gurls" (2 wds.) |
| 36% | LUKECOMBS | 9 | Country singer who had a 2023 hit with his cover of Tracy Chapman's "Fast Car": 2 wds. |
| 36% | SEANPAUL | 8 | Rapper who collaborated with Beyoncé on the 2003 #1 hit "Baby Boy": 2 wds. |
| 35% | JOHNLEGEND | 10 | "All of Me" singer who's back, along with Gwen Stefani, as a veteran coach on "The Voice": 2 wds. |
| 35% | JOHNMELLENCAMP | 14 | "Jack & Diane" singer who had a hit in 1986 with "R.O.C.K. in the U.S.A.": 2 wds. |
| 34% | ELTONJOHN | 9 | Pop star who sang a duet with Lady Gaga on his hit "Your Song" at the 2010 Grammys: 2 wds. |
| 34% | DANIELCAESAR | 12 | "Best Part" singer who's featured, along with Giveon, on 16-Across: 2 wds. |
| 34% | THEWEEKND | 9 | "Starboy" pop singer who had 18 songs on the Billboard Hot 100 during a week in 2016: 2 wds. |
| 34% | ARIANAGRANDE | 12 | "7 Rings" singer who reimagined 18-Across in a 2024 hit with the same title: 2 wds. |
| 33% | MARYTRAVERS | 11 | Folk singer who, in a trio with Peter and Paul, sang the 1963 hit "Puff, the Magic Dragon": 2 wds. |
| 33% | THOMASRHETT | 11 | Singer/songwriter who collaborated with 17-Across, 28-Across, Reba McEntire, and Keith Urban on the country hit "Be a Light" (2 wds.) |
| 32% | MILEYCYRUS | 10 | "Wrecking Ball" singer who's been a judge on "The Voice": 2 wds. |
| 32% | BLAKESHELTON | 12 | "Honey Bee" singer who's been a judge on "The Voice": 2 wds. |
| 32% | MEGANTHEE | 9 | With 46-Across, rapper who collaborated with Beyoncé on the 2020 #1 hit "Savage (Remix)": 2 wds. |
| 32% | SINGLELADIES | 12 | 2008 #1 hit for Beyoncé that had the subtitle "Put a Ring on It": 2 wds. |
| 32% | ERIC | 4 | Singer Church who duetted with Keith Urban on the #1 country hit "Raise 'Em Up" |