| 100% | SINEADOCONNOR | 13 | Singer with the 1990 hit "Nothing Compares 2 U": 2 wds. |
| 76% | SINEAD | 6 | O'Connor with the 1990 hit "Nothing Compares 2 U" |
| 73% | SINEADOCONNOR | 13 | Irish singer who had the #1 hit "Nothing Compares 2 U": 2 wds. |
| 65% | OLIVIARODRIGO | 13 | Singer with the 2021 hit "Good 4 U": 2 wds. |
| 64% | BRITNEYSPEARS | 13 | Singer with the 2001 hit "I'm a Slave 4 U": 2 wds. |
| 58% | LISALOEB | 8 | Singer with the 1994 hit "Stay (I Missed You)": 2 wds. |
| 58% | TAYLORDAYNE | 11 | Singer with the 1988 hit "Don't Rush Me": 2 wds. |
| 57% | CAMILACABELLO | 13 | Cuban-American singer with the 2018 #1 hit "Havana": 2 wds. |
| 57% | RACHELPLATTEN | 13 | Singer with the 2015 hit "Stand by You": 2 wds. |
| 57% | SINEADOCONNOR | 13 | Singer whose "Nothing Compares 2 U" was a #1 song for four weeks in 1990 (2 wds.) |
| 56% | LEWISCAPALDI | 12 | Scottish singer with the 2019 hit "Someone You Loved": 2 wds. |
| 56% | DIXIEDAMELIO | 12 | TikTok star and singer with the 2021 hit "Psycho": 2 wds. |
| 56% | FIONAAPPLE | 10 | "Fruity" female pop singer with the 1997 hit "Criminal": 2 wds. |
| 56% | VANESSACARLTON | 14 | American singer with the 2002 hit "A Thousand Miles": 2 wds. |
| 56% | CALVINHARRIS | 12 | Scottish singer with the 2014 hit "Summer": 2 wds. |
| 56% | BOBBYMCFERRIN | 13 | Singer with the 1988 hit "Don't Worry, Be Happy": 2 wds. |
| 56% | ALISONKRAUSS | 12 | "When You Say Nothing At All" singer who collaborated with Brad Paisley on the 2004 country hit "Whiskey Lullaby": 2 wds. |
| 56% | SHAWNMENDES | 11 | Canadian pop singer with the 2015 hit "Stitches": 2 wds. |
| 56% | LEEGREENWOOD | 12 | "I.O.U." singer who had a hit in 2001 with "God Bless the U.S.A.": 2 wds. |
| 55% | JOHNMELLENCAMP | 14 | "Jack & Diane" singer who had a hit in 1986 with "R.O.C.K. in the U.S.A.": 2 wds. |
| 55% | SAMSMITH | 8 | Singer of the 2014 hit "Stay With Me": 2 wds. |
| 54% | BARRYWHITE | 10 | Singer with the 1974 hit "Can't Get Enough of Your Love, Babe": 2 wds. |
| 54% | ARETHAFRANKLIN | 14 | Classic R&B singer with the 1967 hit "Chain of Fools": 2 wds. |
| 54% | BRYANADAMS | 10 | Singer with the 1985 top 10 hit "Summer of '69": 2 wds. |
| 53% | SHIRLEYMANSON | 13 | Scottish singer with the 2005 hit (with the band Garbage) "Bleed Like Me": 2 wds. |
| 53% | ARIANAGRANDE | 12 | Singer of the #1 hits "Thank U, Next" and "7 Rings": 2 wds. |
| 53% | LINDARONSTADT | 13 | "You're No Good" singer with the 1977 hit single "It's So Easy": 2 wds. |
| 53% | JOSEFELICIANO | 13 | Puerto Rican singer with the perennial holiday hit "Feliz Navidad": 2 wds. |
| 52% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 52% | MICHAELJACKSON | 14 | Singer with the most #1 Billboard Hot 100 hits (9) during the 1980s: 2 wds. |