3. Randy Quaid
Quaid was once very popular, with a stream of film hits in the 80s and early 90s, but he filed for bankruptcy in 2000. Over the next decade, he worked very little and was arrested in 2012 on felony vandalism charges. The Independence Day actor was able to post bond for $500,000 but never showed up in court, forfeiting all the bail money and landing himself even deeper into debt.
(Photo by David Livingston/Getty Images)
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