This is only one episode that was never expanded into a full series, but I have to recommend Mike and Melissa. The first couple times you watch it you will probably be like "what the fuck" but if you're like me it is a really fascinating look into the life of it's creator. The creator (the titular Mike) is clearly a very flawed person but it is really interesting to me thinking about how his situation developed into what you see in the episode and whether or not his actions are healthy. Watching it like fifty times honestly made me consider a lot of things that I hadn't and shaped several of my current opinions. Though I should give a warning that it contains sexually explicit content and misogyny from the main character/author.