| 100% | TONIBRAXTON | 11 | "Un-Break My Heart" singer whose obsession with home decor led to unmanageable debt: 2 wds. |
| 33% | DEMILOVATO | 10 | "Heart Attack" singer whose first TV series lead role was on the Disney Channel's "Sonny with a Chance": 2 wds. |
| 31% | CELINEDION | 10 | Singer whose 1998 song "My Heart Will Go On" debuted at #1: 2 wds. |
| 30% | ILOST | 5 | "___ my heart to her" (fell in love): 2 wds. |
| 29% | LUKECOMBS | 9 | Singer of the 2019 country hit "Beer Never Broke My Heart": 2 wds. |
| 29% | KIKIDEE | 7 | Elton John's "Don't Go Breaking My Heart" duet partner: 2 wds. |
| 29% | ONEI | 4 | "The ___ Gave My Heart To" (1997 Aaliyah song): 2 wds. |
| 29% | TONYBENNETT | 11 | "I Left My Heart in San Francisco" singer honored with the 2017 Gershwin Prize for Popular Song (2 wds.) |
| 28% | ELTONJOHN | 9 | "Your Song" singer whose charitable foundation helps people with AIDS: 2 wds. |
| 28% | KIKIDEE | 7 | Elton John's collaborator on the 1976 hit single "Don't Go Breaking My Heart": 2 wds. |
| 28% | NORAHJONES | 10 | Singer whose "Feels Like Home" album went platinum in one week: 2 wds. |
| 28% | LILYALLEN | 9 | "Smile" and "The Fear" singer whose first name rhymes with "chili": 2 wds. |
| 28% | BILLYJOEL | 9 | "Piano Man" and "Uptown Girl" singer whose first name rhymes with "chili": 2 wds. |
| 28% | WHITNEYHOUSTON | 14 | Singer with seven consecutive #1 singles, from "Saving All My Love for You" to "Where Do Broken Hearts Go": 2 wds. |
| 27% | TONYBENNETT | 11 | "I Left My Heart in San Francisco" singer who's an accomplished painter: 2 wds. |
| 27% | KENNYCHESNEY | 12 | Country singer whose marriage to Renée Zellweger was annulled after just four months: 2 wds. |
| 27% | PAULACOLE | 9 | Singer whose "I Don't Want to Wait" was the theme song for "Dawson's Creek": 2 wds. |
| 27% | TONI | 4 | "Un-Break My Heart" singer Braxton |
| 27% | TONI | 4 | "Un-Break My Heart" singer ___ Braxton |
| 26% | ONEI | 4 | Aaliyah's "The ___ Gave My Heart To" (2 wds.) |
| 26% | GEORGESTRAIT | 12 | "I Cross My Heart" country singer named the ACM Artist of the Decade for the 2000s: 2 wds. |
| 26% | DAMONE | 6 | "You're Breaking My Heart" singer Vic |
| 26% | CHADKROEGER | 11 | Nickelback lead singer whose first name is an African country: 2 wds. |
| 26% | KIKIDEE | 7 | "Don't Go Breaking My Heart" singer, 1976 |
| 26% | DEE | 3 | "Don't Go Breaking My Heart" singer Kiki |
| 26% | SELENAGOMEZ | 11 | "Come & Get It" singer whose first TV series lead role was on Disney's "Wizards of Waverly Place": 2 wds. |
| 26% | PAULSIMON | 9 | Singer whose 1986 hit album 36-Across was named for 28-Across's home (2 wds.) |
| 26% | LUREDIN | 7 | Led to a trap: 2 wds. |
| 25% | MILEYCYRUS | 10 | "Party in the U.S.A." singer whose first TV series lead role was on Disney's "Hannah Montana": 2 wds. |
| 25% | ELLIEGOULDING | 13 | "Love Me Like You Do" singer whose first and last names each start and end with the same letter: 2 wds. |