My personal hero is Uri Geller: I think he went through the most lawsuits

Geller sued Prometheus Books three times but lost and was required to pay more than $20.000 for one process.
Geller sued the magician James Randi three times but lost all of the processes.
In 1991, Geller sued the Timex Watch Company and was sanctioned $149.000 for filing a frivolous lawsuit.
In 1998, the Broadcasting Standards Commission rejected a complaint made by Geller.
In November 2000, Geller sued Nintendo over the Pokémon character "Yungerer," localized in English as "Kadabra," which he claimed was an unauthorised appropriation of his identity. The Pokémon in question has psychic abilities and carries bent spoons. Geller sued for £60 million but lost.
He also considered a suit against IKEA over a furniture line featuring bent legs that was called the "Uri" line.
In March 2007, videos clearly showing Geller cheating were removed from YouTube due to copyright claims by Explorologist Limited.