5. Khloe Kardashian
That’s right, this big-lipped beauty was arrested back in 2007 for a DUI. She was sentenced to community service and an alcohol education class, but after failing to show up for her community service, Khloe K was given 30 days in jail. For some reason, this lucky Kardashian ducky spent a measly 3 hours in a cell, apparently due to overcrowding. Personally, we think she flirted her way out.