|Portrayed by:||Dick Miller|
|Last appearance:||Harley's Holiday|
|Appears in:||2 Episodes|
Boxy Bennett was a fairly powerful gangster who operated in Gotham City.
Boxy ran an underground gambling operation, before Harley Quinn and Batman accidentally stumbled upon it, forcing him to abandon his operation. Despite Harley having been partly responsible for him having to shut down his gambling operation, Boxy still had a thing for Harley and she attempted to use this to get him to sneak her out of town later on, however once again Batman showed up, alongside Robin, and apprehended all of his henchmen. Boxy attempted to get revenge on Harley in retaliation for this, but this proved to be fatal mistake as his attempt to get catch Harley ended up in him being captured in rather embarrassing fashion by Harvey Bullock.