Comedian Andy Daly is an expert at creating naive, offbeat characters with dark secrets. He has appeared in many places (and this AV Club article walks through them all in an interview with Daly), but now has his own show, Review on Comedy Central, in which his character, Forrest, reviews life experiences, from eating 30 pancakes to divorce to being Batman. All 8 of the episodes so far are now online, the funny/dark/uncomfortable parts really start with episode 3: 1, 2, 3, 4, 5, 6, 7, 8. Andy Daly is also a comedy podcast regular, and ran a one-off series where he played a different character every week (the amazing one where he plays a German travel writer, with many other comedians as guests, is a good place to start).
The Dead Authors Podcast: Legendary time-traveling writer H.G. Wells (Paul F. Tompkins) welcomes literary giants to The Upright Citizens Brigade Theatre in Los Angeles for a lively discussion in front of a live audience. Unscripted, barely researched, all fun! [more inside]