| 100% | TONI | 4 | Singer Braxton of "Un-Break My Heart" |
| 80% | TONI | 4 | ___ Braxton, singer of "Un-Break My Heart" |
| 77% | TONI | 4 | "Un-Break My Heart" singer Braxton |
| 77% | TONI | 4 | "Un-Break My Heart" singer ___ Braxton |
| 61% | DAMONE | 6 | "You're Breaking My Heart" singer Vic |
| 60% | KIKIDEE | 7 | "Don't Go Breaking My Heart" singer, 1976 |
| 60% | DEE | 3 | "Don't Go Breaking My Heart" singer Kiki |
| 59% | TONI | 4 | "Unbreak My Heart" singer Braxton |
| 56% | LUKECOMBS | 9 | Singer of the 2019 country hit "Beer Never Broke My Heart": 2 wds. |
| 55% | TONIBRAXTON | 11 | "Un-Break My Heart" singer whose obsession with home decor led to unmanageable debt: 2 wds. |
| 55% | REBA | 4 | "For My Broken Heart" singer McEntire |
| 55% | LIPA | 4 | “Break My Heart” singer Dua |
| 55% | DUA | 3 | "Break My Heart" singer ___ Lipa |
| 53% | DEMI | 4 | ___ Lovato, singer of "Give Your Heart A Break" |
| 53% | ERMA | 4 | "Piece of My Heart" singer Franklin |
| 51% | ERMA | 4 | “Piece of My Heart” singer Franklin |
| 51% | TONI | 4 | ___ Braxton who sang "Un-Break My Heart" |
| 51% | ERMA | 4 | Original "Piece of My Heart" singer Franklin |
| 50% | ISLEY | 5 | "This Old Heart of Mine (Is Weak for You)" singers The ___ Brothers |
| 49% | YOU | 3 | "___ Broke My Heart" (Drake song) |
| 49% | GEORGESTRAIT | 12 | "I Cross My Heart" country singer named the ACM Artist of the Decade for the 2000s: 2 wds. |
| 49% | BRAXTON | 7 | Toni who sang “Un-Break My Heart” |
| 48% | DION | 4 | Singer Celine of "My Heart Will Go On" |
| 48% | EACH | 4 | Madonna "___ Time You Break My Heart" |
| 48% | GRACE | 5 | "___ of My Heart," movie in which Ileana Douglas plays a singer-songwriter |
| 47% | VIC | 3 | "You're Breaking My Heart" crooner Damone |
| 47% | TRACI | 5 | Singer Braxton, sister of Toni |
| 46% | KIKIDEE | 7 | "Don't Go Breaking My Heart" duettist, 1976 |
| 46% | DEE | 3 | "Don't Go Breaking My Heart" vocalist Kiki |
| 46% | DEE | 3 | "Don't Go Breaking My Heart" collaborator Kiki |