The Rapper: Kanye West
The Lawsuit: Jonathan Lee Riches—a federal inmate known for filing crazy lawsuits against celebrities—sued him and Kim Kardashian in 2012 for participating in al-Qaida training camps in West Virginia
Why It Was Dumb: Do we really have to explain this one? There's a reason why Riches is known as "the world's most litigious man."
Photo Credit: Just Jared