That Time I Went To Jail Season 1

That Time I Went To Jail Season 1

In season one, we meet a vastly diverse group of people, from a comedian to a gymnast, who have even more diverse run-ins with the law. Anyone can get stopped by cops, but what happens next largely depends on some pretty unfair factors.

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That Time I Went To Jail Season 1

14 Videos

  • Episode 1 - Amir Ouazzani

    When gymnast Amir Ouazzani was arrested, he put his flexibility to good use. Listen to his story of a daring near-escape and why his arresting officer called him Houdini.

  • Episode 2 - El Sawyer

    When he was 17, El Sawyer shot someone who was trying to rob him and his brother. After being arrested, they were taken into interrogation and what happened there is a testament to brotherly love.

  • Episode 3 - Shawnda Chapman Brown

    Her boyfriend beat her up, but she went to jail. Despite his abuse, Shawnda Chapman Brown didn’t want to press charges against him, an undocumented immigrant. The system must be broken if the only other option was sending her to jail.

  • Episode 4 - Jordan Jensen

    When comedian and carpenter Jordan Jensen was pulled over, the officer found a mighty suspicious combo of items in her car: an axe, wigs, red paint, and syringes. So how did she get off so easy? She made him laugh.

  • Episode 5 - Lee Trice

    Graffiti artist Lee Trice was arrested when cops mistook him for his friend, notorious NYC tagger Dick Chicken. After Lee refused to snitch, officers offered him a Big Mac and told him, “You’re about to go to hell,” aka central booking.

  • Episode 6 - Kevin Richards

    Kevin Richards met his crush at a party, but not in the way he wanted. When she arrived, he was already in cuffs—and in tears—for trying to save the party from aggressive cops. Being the party hero didn’t exactly make him look like Prince Charming.

  • Episode 7 - Hannah Laytner

    This is the story of how almond milk led to one girl’s arrest. Hannah Laytner walked into a party with Silk and came out with Rolling Rock—guess which one is easier to spot by campus police?

  • Episode 8 - Hugh Jones

    How does an innocuous driving offense lead to having three encounters with the cops, your car being completely torn apart for nothing, and not even a single apology? Was it thorough policing or just plain harassment?

  • Episode 9 - Max

    Max was protesting police brutality when he was tackled to the ground by officers in riot gear. The moment was captured and became a widely used photo of resistance. He was immortalized, but he has no memory of it because of his head injury.

  • Episode 10 - Daniel Genis

    During journalist Daniel Genis’ 10-year stint in a maximum security prison, he was sent to solitary four times. His most noteworthy infraction? The unauthorized exchange of five human souls.

  • Episode 11 - Redacted

    When a heroin addict describes withdrawal as “the flu times a million,” the last thing he needs is an arrest interrupting his doping routine. He can either get his fix somehow or have the worst night of his life.

  • Episode 12 - Coss Marte

    Coss Marte recounts his life as an NYC drug dealer, laughs at his old business name (Happy Endings), and describes his arrest. After doing seven years, he founded CONBODY, a gym that hires formerly incarcerated individuals to teach fitness.

  • Episode 13 - Evie Litwok

    After two years in prison, Evie Litwok, a Jewish lesbian and daughter to two Holocaust survivors, founded Witness to Mass Incarceration, which advocates for incarcerated women and LGBTQ people.

  • Episode 14 - Jennifer Montano

    One minute she was driving and the next, Jennifer Montano’s life was forever changed. But her terrible mistake has also given her a new purpose in life: to do better.