The teardrop tattoo or tear tattoo is a symbolic tattoo of a tear that is placed underneath the eye.my Winehouse had a teardrop tattooed to mark her distress at husband Blake Fielder-Civil remaining on remand at Pentonville Prison. Basketball player Amar'e Stoudemire has had a teardrop tattoo since 2012; honoring his older brother Hazell Jr. who had died in a car accident.