Each week, I recommend two podcasts that are worth your time, as well as plug my own podcast.
I agree that comedy podcasts can be incestuous, in that the same guests do the rounds on all the podcasts, and it can make the comedy podcast scene feel like a metaphorical circle jerk. Admittedly, Totally Laime has hosted the usual suspects (Paul F. Tompkins, Pete Holmes, Jake Fogelnest, etc.) but host Elizabeth Laime and sidekick/husband Andy Rosen make it a point to "ask the most important people the least important questions." Even through several guests are in the peak of their career, they make a concerted effort to avoid talking about show business. And thus, that's their spin on the comedic-interview-podcast world.
So, what does that leave to talk about? Everything and anything. Elizabeth and Andy have a way of making their guests open up immediately, and conversations range from cats, how to make friends as an adult, getting your first period, death, Oprah, and embarrassing moments. They create an atmosphere in which I feel like I am at Sunday brunch just shooting the shit with friends, and it is both comforting and hilarious.
Unlike a lot of interview-type podcasts, there is no set agenda or questions, the hosts just let the conversation go where it goes, and being game to talk about anything and to share anything from her personal life that relates to it. There are two regular enjoyable segments, "Laime or Totally Rapidfire" in which guests have to give their first reactions to a variety of words, such as: vegetarians, PDA, and the always-controversial "bald vaginas." Each episode also closes with Elizabeth reading a description of an Oprah Winfrey episode to discuss. Even if you are not an Oprah fan, it creates some of the best reaction moments of the show.
Remember when I mentioned I liked podcasts because it makes me feel like I am hanging out with friends but don't need to talk? Totally Laime is the perfect example of this. Elizabeth and Andy are pretty open about their lives, and are open about sharing their insecurities and vulnerabilities have no reason to doubt that they are not being their true selves on the mic. They are like the couple friends you aspire to be like in a relationship.
The Dead Authors Podcast
Between the hundreds of other podcast appearances and his own podcast, Tompkins hosts The Dead Authors Podcast, recorded live at the mecca of alternate comedy, The Upright Citizens Brigade Theater in Los Angeles. Tompkins plays author H.G. Wells and hosts talks with other dead authors, played by impressive comedic improvisers.
For me, the most impressive comedy is when someone fully takes on a character and can improvise as that character no matter what the situation is. This show is full of people at the top of their game. Be sure to check out the episode with both Friedrich Nietzsche and H.P. Lovecraft, and believe me, you don't need to be versed in those authors to enjoy it. Obviously, this podcast takes an absurdist, exaggerated take on the authors' personalities. Although you don't need to be completely versed in the author's works, it does provide an opportunity to experience some humor based on an intellectual topic. Finally, that liberal arts degree is useful for something!