| 100% | LUISFONSI | 9 | Singer who hit #1 in 2017 with the Spanish/English-language "Despacito": 2 wds. |
| 68% | SHAKIRA | 7 | Singer who hit #1 in 2006 with the Spanish/English-language "Hips Don't Lie" |
| 60% | EDSHEERAN | 9 | Singer who collaborated with Beyoncé on the 2017 #1 hit "Perfect Duet": 2 wds. |
| 56% | LOSDELRIO | 9 | Duo that hit #1 in 1996 with the Spanish/English-language "Macarena": 3 wds. |
| 55% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 53% | ARIANAGRANDE | 12 | "7 Rings" singer who reimagined 18-Across in a 2024 hit with the same title: 2 wds. |
| 53% | LEEGREENWOOD | 12 | "I.O.U." singer who had a hit in 2001 with "God Bless the U.S.A.": 2 wds. |
| 52% | JOHNMELLENCAMP | 14 | "Jack & Diane" singer who had a hit in 1986 with "R.O.C.K. in the U.S.A.": 2 wds. |
| 51% | KATYPERRY | 9 | Singer who collaborated with Snoop Dogg on the 2010 No. 1 Billboard hit "California Gurls" (2 wds.) |
| 50% | TOBYKEITH | 9 | Singer who duetted with Willie Nelson on the 2003 #1 country hit "Beer for My Horses": 2 wds. |
| 50% | GERIHALLIWELL | 13 | Singer who had four #1 hits in the UK from 1999 to 2001, including "It's Raining Men": 2 wds. |
| 48% | RICKYMARTIN | 11 | "Livin' la Vida Loca" singer who records in both English and Spanish: 2 wds. |
| 48% | SANTANA | 7 | Group that hit #1 in 2000 with the Spanish/English-language "Maria Maria" |
| 48% | TODDRUNDGREN | 12 | Singer who came up with "Bang the Drum All Day" in his sleep: 2 wds. |
| 48% | SELENAGOMEZ | 11 | "Hands to Myself" singer who records in both English and Spanish: 2 wds. |
| 48% | JUDYCOLLINS | 11 | Folk singer who sang the 1975 hit "Send in the Clowns": 2 wds. |
| 47% | ALESSIACARA | 11 | "Stay" singer who won the Pop Album of the Year Juno in 2017: 2 wds. |
| 46% | LADYGAGA | 8 | "Poker Face" singer who was the featured act in the 2017 Super Bowl halftime show: 2 wds. |
| 46% | YOLANDAADAMS | 12 | "Already Alright" singer who was inducted into the Gospel Music Hall of Fame in 2017: 2 wds. |
| 46% | JIMMIEALLEN | 11 | "Best Shot" singer who collaborated with Brad Paisley on the 2021 country hit "Freedom Was a Highway": 2 wds. |
| 45% | SHERYLCROW | 10 | "All I Wanna Do" singer who collaborated with Kid Rock on his biggest pop hit, "Picture," in 2002: 2 wds. |
| 45% | EDSHEERAN | 9 | "Shape of You" pop singer who had 13 songs on the Hot 100 during a week in 2017: 2 wds. |
| 45% | 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. |
| 45% | ALISONKRAUSS | 12 | "When You Say Nothing At All" singer who collaborated with Brad Paisley on the 2004 country hit "Whiskey Lullaby": 2 wds. |
| 44% | SINEADOCONNOR | 13 | Irish singer who had the #1 hit "Nothing Compares 2 U": 2 wds. |
| 44% | BRUNOTONIOLI | 12 | "Dancing with the Stars" judge who is fluent in five languages (2 wds.) |
| 44% | HARRYSTYLES | 11 | "Sign of the Times" pop singer who released a self-titled #1 album in 2017: 2 wds. |
| 44% | MICHAELSTIPE | 12 | Singer who came up with "It's the End of the World as We Know It (And I Feel Fine)" in his sleep: 2 wds. |
| 44% | SHEENAEASTON | 12 | "Strut" singer who Prince encouraged and collaborated with in the 1980s: 2 wds. |
| 43% | MARYTRAVERS | 11 | Folk singer who, in a trio with Peter and Paul, sang the 1963 hit "Puff, the Magic Dragon": 2 wds. |