5. Mayhem Miller
Mayhem gets arrested all the time, often for ridiculous reasons or in hilarious fashion. In 2012 he was evidently without a place to sleep so he broke into a church, stripped down naked and decided to crash there. Unfortunately for Miller police arrived on the scene and arrested him.
In 2014 police were attempting to arrest Miller but ended up in a five hour standoff with him that resulted in the SWAT team being called in. Miller was live tweeting updates of the arrest, because that is the kind of thing that Mayhem Miller does.