| 100% | SINEADOCONNOR | 13 | Irish singer who had the #1 hit "Nothing Compares 2 U": 2 wds. |
| 65% | SINEADOCONNOR | 13 | Singer with the 1990 hit "Nothing Compares 2 U": 2 wds. |
| 58% | LEEGREENWOOD | 12 | "I.O.U." singer who had a hit in 2001 with "God Bless the U.S.A.": 2 wds. |
| 57% | NICKIMINAJ | 10 | "Anaconda" singer who has lived in both Trinidad and the US: 2 wds. |
| 57% | GERIHALLIWELL | 13 | Singer who had four #1 hits in the UK from 1999 to 2001, including "It's Raining Men": 2 wds. |
| 57% | JOHNMELLENCAMP | 14 | "Jack & Diane" singer who had a hit in 1986 with "R.O.C.K. in the U.S.A.": 2 wds. |
| 56% | GEORGEMICHAEL | 13 | Lead singer of Wham! who had the 1988 solo hit "Faith": 2 wds. |
| 56% | SEANKINGSTON | 12 | "Beautiful Girls" singer who has lived in both Jamaica and the US: 2 wds. |
| 52% | TAYLORSWIFT | 11 | Singer who has had 12 #1 hits, including "Blank Space": 2 wds. |
| 52% | ARIANAGRANDE | 12 | "Thank U, Next" singer who's had seven songs debut at #1 on the Billboard Hot 100: 2 wds. |
| 51% | SINEADOCONNOR | 13 | "Nothing Compares 2 U" singer who rocked a shaved head: 2 wds. |
| 51% | MARIAHCAREY | 11 | Singer who has had 19 #1 hits, including "Emotions": 2 wds. |
| 51% | ENYA | 4 | Irish singer who had the 2000 top 10 hit "Only Time" |
| 50% | JENNIFERLOPEZ | 13 | American singer and actress who has made hits like "On the Floor": 2 wds. |
| 50% | IGGYAZALEA | 10 | "Fancy" singer who is one of only two music acts to have their first two hit singles rank #1 and #2 simultaneously on the U.S. "Billboard" Hot 100 chart (2 wds.) |
| 50% | ARIANAGRANDE | 12 | Singer of the #1 hits "Thank U, Next" and "7 Rings": 2 wds. |
| 49% | JUDYCOLLINS | 11 | Folk singer who sang the 1975 hit "Send in the Clowns": 2 wds. |
| 49% | AKON | 4 | Singer who had the #1 hit "Don't Matter" |
| 49% | TAYLORSWIFT | 11 | "Cardigan" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 49% | LADYGAGA | 8 | "Shallow" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 48% | JASONDERULO | 11 | "Wiggle" R&B singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 48% | LUISFONSI | 9 | Singer who hit #1 in 2017 with the Spanish/English-language "Despacito": 2 wds. |
| 48% | EDSHEERAN | 9 | Singer who collaborated with Beyoncé on the 2017 #1 hit "Perfect Duet": 2 wds. |
| 48% | JONIMITCHELL | 12 | Folk singer who sang the 1974 hit "Big Yellow Taxi": 2 wds. |
| 48% | ALISONKRAUSS | 12 | "When You Say Nothing At All" singer who collaborated with Brad Paisley on the 2004 country hit "Whiskey Lullaby": 2 wds. |
| 47% | SINEAD | 6 | O'Connor with the 1990 hit "Nothing Compares 2 U" |
| 47% | RAYCHARLES | 10 | "Hit the Road Jack" singer who has a solo in 1985's "We Are the World": 2 wds. |
| 47% | ARIANAGRANDE | 12 | "Yes, And?" singer who had two songs reach #1 on the Billboard Hot 100 in 2024: 2 wds. |
| 47% | TINATURNER | 10 | "Private Dancer" singer who has a solo in "We Are the World": 2 wds. |
| 46% | KATYPERRY | 9 | Singer who collaborated with Snoop Dogg on the 2010 No. 1 Billboard hit "California Gurls" (2 wds.) |