Teardrop tattoos or tattoo tears can symbolize many things, including the death of a loved one or friend, a warning to others that the wearer murdered someone or the number of years the wearer was incarcerated.
The teardrops are drawn differently to convey a particular meaning. For instance, those who have a friend or a family member that was killed and are seeking for revenge have an empty teardrop tattoo. Once revenge is fulfilled, the teardrop is filled with ink.
Amar'e Stoudemire of the New York Knicks has a teardrop tattoo underneath his eye to honor his brother, who died in a car accident.