The term 'Achy Breaky Heart Singer' refers to three popular singers: CYRUS (5 letters), Dayne (5 letters), and Cole (4 letters). CYRUS is the stage name of Billy Ray CYRUS, an American singer-songwriter and actor who released the hit single 'Achy Breaky Heart' in 1992. Taylor Dayne is an American singer-songwriter who released a cover version of 'Achy Breaky Heart' in 1993. Finally, Gary Allan Cole, known professionally as Gary Allan, is an American country music artist who released a cover version of 'Achy Breaky Heart' in 1994.