You gaze into the hobo's eyes, hypnotize him, and force him to do something really, really embarrassing. I'm not gonna say exactly how embarrassing, but suffice to say it deals X damage.
Notes
X is 2 or 3 times the enemy's remaining HP. This will kill any hobo instantly, but Hobopolis bosses and the gang of hobo muggers take much less due to their damage reduction.
