| 100% | MACYGRAY | 8 | "Colorful" singer of the 2000 top-5 hit "I Try": 2 wds. |
| 62% | MORGANWALLEN | 12 | Singer of the 2020 top 10 hit "7 Summers": 2 wds. |
| 60% | SHEENAEASTON | 12 | Singer of the 1980s hit "Morning Train (9 to 5)": 2 wds. |
| 60% | SAMSMITH | 8 | Singer of the 2014 hit "Stay With Me": 2 wds. |
| 58% | BRYANADAMS | 10 | Singer with the 1985 top 10 hit "Summer of '69": 2 wds. |
| 57% | MANDYMOORE | 10 | Singer of the hit 2000 single "I Wanna Be With You", who also voiced the role of Rapunzel in the animated film "Tangled": 2 wds. |
| 53% | GARTHBROOKS | 11 | Singer of the 2000 song "Wild Horses": 2 wds. |
| 52% | KELLYCLARKSON | 13 | Singer of the 2015 hit "Heartbeat Song": 2 wds. |
| 52% | RACHELPLATTEN | 13 | Singer of the 2015 hit "Fight Song": 2 wds. |
| 52% | SARABAREILLES | 13 | Singer of the 2007 hit "Love Song": 2 wds. |
| 52% | EDSHEERAN | 9 | Singer of the 2019 hit "Beautiful People": 2 wds. |
| 52% | LUKECOMBS | 9 | Singer of the 2018 hit "Beautiful Crazy": 2 wds. |
| 52% | ARIANAGRANDE | 12 | Singer of the 2019 #1 hit "7 Rings": 2 wds. |
| 51% | ALGREEN | 7 | Singer of the 1972 hit "Let's Stay Together": 2 wds. |
| 51% | ALESSIACARA | 11 | Singer of the 2016 hit "Scars to Your Beautiful": 2 wds. |
| 51% | AALIYAH | 7 | Singer of the 2000 #1 hit “Try Again” |
| 50% | LUKECOMBS | 9 | Singer of the 2019 country hit "Beer Never Broke My Heart": 2 wds. |
| 50% | ARIANAGRANDE | 12 | Singer of the #1 hits "Thank U, Next" and "7 Rings": 2 wds. |
| 50% | LADYGAGA | 8 | Singer of the #1 hits "Just Dance" and "Born This Way": 2 wds. |
| 50% | KENNYCHESNEY | 12 | Singer of the 2007 #1 country hit "Beer in Mexico": 2 wds. |
| 50% | LUKEBRYAN | 9 | Singer of the 2014 #1 country hit "Drink a Beer": 2 wds. |
| 50% | MACYGRAY | 8 | September-born R&B singer with the Top 10 hit "I Try" (2 wds.) |
| 49% | RICKYMARTIN | 11 | Puerto Rican singer of the 1999 hit "Livin' la Vida Loca": 2 wds. |
| 49% | DREWBARRYMORE | 13 | Star and producer of the 2000 hit film "Charlie's Angels": 2 wds. |
| 49% | TROYESIVAN | 10 | Singer of the 2015 hit "Youth" who was born in South Africa in 1995: 2 wds. |
| 48% | TAYLORSWIFT | 11 | Singer of the 2019 pop song "ME!": 2 wds. |
| 48% | ISAACHAYES | 10 | Singer of the 1971 #1 hit song "Theme from Shaft" (2 wds.) |
| 48% | THEOSMONDS | 10 | Singers of the 1971 #1 hit song "One Bad Apple" (2 wds.) |
| 48% | TAYLORSWIFT | 11 | "Cardigan" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 48% | LADYGAGA | 8 | "Shallow" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |