Randy Quaid
After a stellar run of hits in the 80s and early 90s, Randy Quaid filed for bankruptcy in 2000. The next decade, he worked very little and was arrested in 2012 on felony vandalism charges. Somehow, he coughed up with $500,000 to post bond and get out of jail, but Randy never showed up in court, forfeiting all the bail money and digging himself even deeper into debt.