| 100% | GLORIAESTEFAN | 13 | Cuban-American singer with the 1991 #1 hit "Coming Out of the Dark": 2 wds. |
| 59% | CAMILACABELLO | 13 | Cuban-American singer with the 2018 #1 hit "Havana": 2 wds. |
| 58% | GLORIAESTEFAN | 13 | "Coming Out of the Dark" singer who, with her husband Emilio, won the 2019 Gershwin Prize: 2 wds. |
| 52% | GLORIAESTEFAN | 13 | "Coming Out of the Dark" singer who's part owner of the Miami Dolphins: 2 wds. |
| 50% | VANESSACARLTON | 14 | American singer with the 2002 hit "A Thousand Miles": 2 wds. |
| 50% | BRYANADAMS | 10 | Singer with the 1985 top 10 hit "Summer of '69": 2 wds. |
| 49% | DICKSARGENT | 11 | "Bewitched" actor who came out of the closet in 1991 at age 61: 2 wds. |
| 48% | BARRYWHITE | 10 | Singer with the 1974 hit "Can't Get Enough of Your Love, Babe": 2 wds. |
| 48% | BARRYGIBB | 9 | September-born disco singer with the Top 10 hit "What Kind of Fool" (2 wds.) |
| 47% | SAMSMITH | 8 | Singer of the 2014 hit "Stay With Me": 2 wds. |
| 47% | ARETHAFRANKLIN | 14 | Classic R&B singer with the 1967 hit "Chain of Fools": 2 wds. |
| 47% | PHILCOLLINS | 11 | Singer with the 1988 #1 song “Groovy Kind of Love”: 2 wds. |
| 46% | MARTIKA | 7 | Cuban-American singer with the 1989 #1 hit "Toy Soldiers" |
| 46% | WHITNEYHOUSTON | 14 | "I Will Always Love You" singer with a memorable 1991 Super Bowl performance of the national anthem: 2 wds. |
| 46% | ARETHAFRANKLIN | 14 | Singer who spells out the title of her 1967 hit "Respect": 2 wds. |
| 46% | ARIANAGRANDE | 12 | Singer who spells out the title of her 2019 hit "NASA": 2 wds. |
| 46% | PETERCETERA | 11 | Singer with the 1986 #1 song “Glory of Love”: 2 wds. |
| 46% | STEVIEWONDER | 12 | American singer with 25 Grammy Awards famous for his song "You Are the Sunshine of My Life": 2 wds. |
| 45% | QUEENLATIFAH | 12 | Singer who spells out the title of her 1994 hit "U.N.I.T.Y.": 2 wds. |
| 45% | MICHAELJACKSON | 14 | Singer with the most #1 Billboard Hot 100 hits (9) during the 1980s: 2 wds. |
| 45% | JOHNLEGEND | 10 | Ivy Leaguer (he went to Penn) with the 2014 #1 hit "All of Me": 2 wds. |
| 44% | LUISFONSI | 9 | Singer who hit #1 in 2017 with the Spanish/English-language "Despacito": 2 wds. |
| 44% | JONASBROTHERS | 13 | Trio of former Disney Channel stars with the 2019 #1 hit "Sucker": 2 wds. |
| 44% | ARIANAGRANDE | 12 | Singer of the 2019 #1 hit "7 Rings": 2 wds. |
| 44% | MARIAHCAREY | 11 | Singer (with Miguel) of the 2013 hit "#Beautiful": 2 wds. |
| 44% | ABDUL | 5 | Singer with the 1991 #1 hit "Rush, Rush" |
| 44% | SINEADOCONNOR | 13 | Singer with the 1990 hit "Nothing Compares 2 U": 2 wds. |
| 44% | TAYLORDAYNE | 11 | Singer with the 1988 hit "Don't Rush Me": 2 wds. |
| 43% | EDSHEERAN | 9 | Singer who collaborated with Beyoncé on the 2017 #1 hit "Perfect Duet": 2 wds. |
| 43% | KENNYCHESNEY | 12 | Singer of the 2007 #1 country hit "Beer in Mexico": 2 wds. |