In 1995 an inmate tried to sue himself for $5 Million because he violated his own civil rights by getting arrested – then asked the state to pay because he has no income in jail.
Keanu Reeves was sued by a woman who suggested that he used hypnosis and impersonated her ex-husband to impregnate her. She sought $3 million in spousal support from the actor, and $150,000/month, retroactively, in child support. DNA test proved he was not the father and the suit was thrown out.
A Montana State University Professor sued Walmart because they put his occupation as “Toilet Cleaner” on his fishing license.
A Chicago grocery store ran an ad congratulating Michael Jordan on entering the NBA Hall of Fame. Jordan sued and won $8.9 million for using his name.
When Eminem was sued in 2003 by the bully, DeAngelo Bailey for slandering him in the song “Brain Damage”, the judge threw out the case and provided the ruling by rapping it.
A man once sued Satan for depriving him of his constitutional rights. The judge dismissed the case because the plaintiff had not included instructions for how a U.S. Marshal could serve process on Satan.
The Beastie Boys won a lawsuit against a company for the unauthorized use of their song “Girls” and had the $1 Million settlement donated to a charity supporting education for girls.
In 1995, McDonald’s asked Greenpeace activists to stop criticizing their company publicly and instead do it only in private with their friends. Activists said they’d agree if McDonald’s stopped advertising its products and instead only recommended their restaurants privately to friends.
In 2008, a manager at BusinessWeek magazine in New York became trapped in an elevator for 41 hours. The lawsuit ($25 million) he eventually filed against the building’s management company took 4 years to complete during which time he lost his job, his money, his colleagues and his apartment.
In 2009, an abusive litigant sued a man for $30k for selling him a $40 printer on Craigslist, claiming it was broken. The case lasted for 6½ years and, as of 2016, may still be on-going.