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Street Walking is a dramedy following Tommy Walker who gets broken up with and turns to a podcast Cashing In with T.J. Miller for comfort through comedy. He realizes he wants to help others by starting his own podcast, but he doesn't have any money for equipment. Tommy gets a job at a convenience store to pay for his podcast. Once he gets the money, he starts his podcast "Street Walking with Tommy Walker" by asking people on the street to be on his podcast. It's forced and not funny, so he is unhappy with it. He goes to see T.J. Miller do stand up live and gets to meet him after the show. They talk about the absurdist philosophy and Tommy realizes he needs to talk about life philosophy with people and make a genuine connection. The funny will come because he's funny, but it isn't the focus. Tommy stops looking for validation outwards and finds it in himself and Tommy now finds the funny in every situation even how the love of his life left him for another person with the same name.