| TAIO | Cruz who hit No. 1 with "Break Your Heart" |
| TAIOCRUZ | English singer-songwriter, rapper, and record producer who topped the charts with Break Your Heart in 2009 and Dynamite in 2010 (4,4) |
| CARNES | Kim who hit No. 1 with "Bette Davis Eyes" |
| LORDE | What New Zealand singer who hit No. 1 with "Royals," is of Croatian descent on her mother's side? |
| MARCELS | With "the," doo-wop band who hit No. 1 in 1961 with the ballad "Blue Moon" |
| TROGGS | They hit No. 1 with "Wild Thing" in 1966 (with "the") |
| SLY | Stone who hit No. 1 in 1970 with "Thank You (Falettinme Be Mice Elf Agin)" |
| LAUPER | She hit No. 1 with "True Colors" |
| CHER | She hit No. 1 with "Believe" |
| LEARNINGTOFLY | Tom Petty song with the lines, "Well some say life will beat you down / Break your heart, steal your crown" |
| TRL | Show whose first #1 video was Backstreet Boys' "I'll Never Break Your Heart" |
| AIR | What can hit you in the face or break your heart, according to Talking Heads |
| IFHE | Journey's "___ ___ Should Break Your Heart" |
| ANTHRACITE | I burn, but break your heart? I can't! (10) |
| STRESS | Can't make this point strongly enough - this could break your heart (6) |
| WILCO | "I Am Trying to Break Your Heart" band |
| CARDIAC | Joker with one account breaks your heart perhaps (7) |
| CORONARY | Mary half follows the glow from Son reportedly - it would break your heart (8) |
| OPERA | What Julian Barnes called "an art which seeks, more obviously than any other form, to break your heart" |
| DIETRICH | "It makes no difference how she breaks your heart if she is there to mend it," said Ernest Hemingway |
