Crime: Various, drug related Served: Multiple totalling about 2 years Robert Downey Jr. is literally the biggest actor in the world. Thanks to Marvel, as well as some other choice roles, hes got a massive fan-base and reaps in vast mounds of cash that would make even Tony Stark jealous. The situation just over a decade ago was rather different. Downey Jr.s problems with drugs had been well documented, the initial praise of his turns in the likes of Chaplain and Natural Born Killers making way for reams of print on his downward spiral. Arrested multiple times, he eventually got a lengthy three year sentence in 1999 after breaking his probation multiple times. In what is probably the biggest example of how the law can be bent for celebrities, he only served one year of this; the judge ruled (on the flimsy basis that the collected times hed spent in a cell previously counted to this charge) that hed served enough.