10. Matthew McConaghey
In the late nineties, McConaghey was seriously beginning his rise to major stardom. He'd already appeared in Amistad and Contact by that point and Edtv was released the same year as his short prison stay. Unsurprisingly it was on a drugs charge. The police went around to his house at 3am following a neighbour's complaint that he was playing music too loud for the early hours of the morning. They found McConaghey naked, dancing around a room while playing some bongos. Another man sat and clapped along. McConaghey pushed around the cops and was charged for drug possession as well as resisting transportation. He ended up spending nine hours in jail before being released on a bond. In response, McConaghey claimed the police entered the property illegally and the police used excessive force in arresting him. But he had a good time in his short stay, he later recalled how he got his cell mates to join him in a sing along.