Pro Se litigation — where the plaintiff is her/his own lawyer — is a hotbed of legal humor. Lowering the Bar rounds up some of the weirdest examples from recent history:
Joan Newberger v. Department of Wildlife & Fishery, State of Louisiana: Lawsuit for ADA violations and wrongful seizure. The plaintiff's four service monkeys were taken from her as she attempted to change their diapers and feed them on Bourbon Street. [ed: the monkeys were dressed as pirates]
Ray Miles v. State of Kansas; Kansas Highway Patrol; Capitol Police: Petition to be "left the f*ck alone" where the defendants harassed the plaintiff for "no reason." $100 million.