Gaolers, also called Wardens or Jailers, are known for keeping prisoners in check. These villains are feared for or known to imprison their captives, whether it is in a jail cell, a cage, etc. For obvious reasons, the vast majority of these villains are Corrupt Officials. Many are also Psychopaths who enjoy tormenting their victims by imprisoning them (e.g. Buffalo Bill from The Silence of the Lambs). Ironically, some Gaolers can be Prisoners themselves.

Gaolers can qualify as Pure Evil if they imprison innocent people and torture their prisoners such as Lots-O' Huggin' Bear who acted as a penitentiary warden and broke toys physically and psychologically by making Sunnyside Daycare a hellish place as well as Infinite who tortured Sonic for six months before wanting to have him thrown out into space so he could see his world become an utter hell before he died.

There are also certain kinds of Gaolers who can be known under a distinct subcategory known as Trap Masters. Trap Masters are those who are skilled at ensnaring and trapping others, thereby leaving them to be imprisoned.