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Frank Boles was a vicious, brutal security guard at Arkham Asylum. Before his death on the night of the Joker’s attempt to poison Gotham City with Titan, Boles had twice been suspended during his eight years at Arkham for drinking on the job. After soliciting the Joker’s help in an unexplained situation, Boles regularly assists the Clown Prince of Crime in his criminal escapades. 

Batman: Arkham Asylum

When Joker plans to break in to Arkham Asylum to steal Dr. Penny Young’s formula for Titan, he calls on Boles to help him escape custody. Once Joker has taken control of Arkham Island, Boles kidnaps Commissioner Gordon and escorts him to Harley Quinn.

Batman tracks Boles by analyzing the spilled bourbon from his flask and locates the Arkham guard near the exit of Intensive Treatment. Boles had previously been heard on the intercom ambushing and murdering a number of his fellow guards, before handing Gordon over the Quinn. The petty thug’s reign of terror is short lived, however, as Batman finds his corpse tied to a prisoner transport cart with “Dead End” written on a sign hung around his neck. The green smile and white makeup affixing the corpse left no doubt who was responsible for the corrupt guard’s demise and Batman continued his pursuit of the Joker.    

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