I enjoy watching: Free Radio and Head Case. Both are outrageously funny and have the most embarrassing situations.
Head Case is about this psychiatrist who lives in a hotel, and is unethical and emotionally unstable i.e. A mess. She is a psychiatrists to the stars, all her clients are celebrities, but she talks about how screwed up her clients are to everybody. This show is off the hook.
Free Radio is a show about a radio program that airs in the morning and has 2 hosts, one of them is this clueless host, lance, who utters the most embarrassing things on air. The show has a unique thing going on, it is completely improvised, and the guests who appear on their morning show are real celebrity guests promoting real events and projects.
