Batman: Arkham Asylum (Videogame)
Officer Frank Boles was a corrections officer at Arkham Asylum. Officer Boles eventually joined Joker’s inner circle. Boles would often assist Joker with his escape attempts in exchange for favors. Boles was well aware of the Joker holding Jason Todd prisoner in an abandoned wing of Arkham Asylum but nothing more ever came of it.
Later on, Joker informs Boles that he has devised a plan to entrap the Batman at Arkham Asylum. After being captured by the Batman and reprocessed at Arkham Asylum, the Joker sprang his trap with the help of Harley Quinn. When Batman chased after the Joker, he noticed a security feed that showed Boles knocking Commissioner Gordon unconscious.
Batman gives up the chase and makes his way to the processing center where he left Gordon. Batman finds Boles’ flask and tracks the unique scent in order to locate Boles. Joker eventually realizes that the Batman is no longer playing his little game because he is too busy tracking down Boles in order to get to Gordon.
Joker gives Harley the order to kill Boles and dress him up as a means to antagonize the Batman. When Batman finds Boles, he discovers his body has been tied to a gurney in a vertical position. Boles’ face is done up to look like the Joker with a big sign tied to his chest saying “Ha Ha Ha”
Prime Earth (Mainstream comic books)
Frank Boles was a security guard at the Arkham Asylum and was patrolling near the cell of Solomon Grundy. He was lured out of the Asylum and killed by the Emerald Empress just a few seconds later.