Ambrose Spellman - Chilling Adventures of Sabrina
After 75 years of house arrest, Ambrose is freed for a short time before being framed by Father Blackwood for killing the Anti-Pope. He's thrown into a jail cell for treason and murder, and though we all know he isn't guilty, the Weird Sisters put him through torture nevertheless while Blackwood is out of town.
Cyrus Beene - Scandal
Cyrus' time in prison was hard to watch, and though he's committed some heinous acts during his political career, you couldn't help but feel bad for him because he wasn't guilty of ordering Tom Larsen to kill President-elect Frankie Vargas. They even threatened Cyrus with the death penalty. And the moment he was freed, you remembered why he deserved to be locked up.
Leonard Peabody - Umbrella Academy
Leonard Peabody's is a product of circumstance. Peabody's father became an abusive alcoholic after his mother died giving birth to him. He tried to find solace by joining the Umbrella Academy, but they shunned him and turned him away. When his father hit him, he murdered his father with a hammer and was put away for 12 years.
Erica Shepard - The Enemy Within
Erica Shepherd went from being of the CIA's most brilliant agents to America's biggest traitor after spying for a terrorist. As she's serving a life sentence in a Supermax prison, she teams up with Will, an FBI agent whose life she ruined, in order to track down the terrorist and save her daughter's life.
Shadow - American Gods
The show kickstarts with Shadow being released early from prison for good behavior after serving three years of his six-year sentence. It takes a bit to figure out what Shadow was in prison for, but we eventually find out that his late wife convinced him to rob a VCR repair store. When he realized the two conspirators were planning to take his cut, he beat them to a bloody pulp.
Sam & Dean - Supernatural
It's a mission simply to keep up with all the times Sam & Dean have been arrested! They've been put away on suspicion of murder, for breaking into hotel rooms, for assault, for overdosing -- the list goes on and on.