Courtney Love
When her husband, Kurt Cobain, committed suicide in 1994, Love inherited a $150 Million fortune as a part of his stake in Nirvana. She ended up selling those publishing rights ($27 Million worth) to pay off several lawsuits, most notably a Twitter defamation suit.
Back in 2009, she was in a battle with a fashion designer, over a spat about a $4K price for clothing. That spiralled into a twitter rant that cost her $430,000 to settle out of court. Then she said some things on The Howard Stern Show, and was forced to pay another $350,000.
Then she tweeted out that her former attorney was bought off through the whole Twitter defamation trial, and was sued for millions by the lawyer.
Best to not say anything at all on Twitter.