The classic silly suit has to be the one about Disneyland being sued because kids saw the characters backstage without their heads on and were traumatised. According to the redoubtable Snopes website this happened twice, but only as smaller parts of more substantial cases.
Beyond much doubt is that there is a town called Batman in Turkey, whose mayor tried to sue director Chris Nolan and Warner Brothers for using the Batman name. Why he left DC Comics, the TV show and all the other merchandisers since 1939 alone (and indeed Dailyfinance owner AOL, which for a period shared the ownership when it was part of Time Warner) is anybody's guess.
Another favourite lawsuit has to be Lord Archer, then plain Jeffrey Archer, gaining £500,000 by convincing a jury that he hadn't slept with a prostitute as the press had alleged. He also got $700,000 in costs. A few years later he was found guilty of perjury in the original case and jailed for four years.
Two for the pot
In 1991 someone sued Budweiser's manufacturer because the beer failed to make him pull beautiful women. I've been drinking beer solidly since that year and can assure everyone that without exercise to balance up the calories he's got a point, it doesn't help.
The all-time best lawsuit and payout, for us, has to be the 1956 trial in with insanely camp pianist Liberace took £8,000 off the Daily Mirror (in context: 11 years later my parents bought a three bed house in London for £7000) for alleging he was homosexual (this was illegal at the time; I freely accept that nobody ought to have given a damn anyway).
He denied this until his death in 1987 from an HIV-related complication, a few years after his chauffer had attempted to sue for palimony after they split up.
Our top 5 crazy litigation in full:
5. Disney forced to pay out over headless characters - qualified and at no. 5 because of other circumstances.
4. Batman sues Batman for copyright
3. Lord Archer sues over his good character
2. Budweiser fails to make you attractive to women
1. Liberace wasn't gay. Honest.
Other examples would be welcome - unless you think suing for boring someone with adverts tops the lot..?
Links (opens new windows)
Guardian on cinema being sued