Pod-Canon is an ongoing tribute to the greatest individual comedy-related podcast episodes of all time.
When Pete Holmes invited Eric Andre, Jackie Kashian, Brett Gelman, and Jon Glaser to be guests on a live You Made It Weird recorded at San Francisco’s Outside Lands back in 2012, there was a good chance that the results would be, well, weird. This is partially due to the nature of the panel. Eric Andre, Gelman, and Glaser all traffic extensively in the comedy of awkwardness. They delight in antagonizing audiences with crazy ideas and trippy, high-concept weirdness seemingly designed to challenge and push audiences away more than entertain them.
Andre, Gelman, and Glaser similarly are tricky to interview because they have such strong stage personas that it can be tough to determine where the meta, fictional, confrontational versions of them end and their real selves begin. But the episode’s weirdness is also attributable to the location. Festivals are a strange universe onto themselves, and I’m not just saying that because I am a five-time visitor to the Gathering of the Juggalos.
At festivals, a lot of the audience are liable to be drunk or high, the performers might be drunk and/or high as well, and live podcasts in general tend to be more unpredictable than conventional tapings. There’s a live crowd the performers are playing to just as much as theoretical later podcast listeners, and with it the opportunity to do visual bits guaranteed to not play in an audio medium like podcasts.
The live Outside Lands podcast more than lived up to its potential for cringe-inducing awkwardness and listening to the podcast four years later, it’s tough to determine how much of it is an elaborate put-on, how much of it is sincere, and how much of it is a weird combination of the two. Sure enough, the episode description on Nerdist hails it as “The weirdest, most uncomfortable episode ever” before admonishing listeners, “Soak in the weirdness, then shower afterwards. NOT FOR THE FAINT OF AWKWARDNESS!”
But before things get unforgettably weird on You Made It Weird, the show begins on an appropriately goofy, giddy, silly, child-like, very Peter Holmes note with Eric Andre goofing on his ancient Haitian father’s exuberance over discovering the magic of Google. Andre does a pretty dead on impression of Holmes, although to be fair, Holmes has such a distinctive voice and a distinctive cadence that he’s almost as irresistible a subject for impersonation as Jack Nicholson.
The light, stream-of-consciousness vibe and riffing continues with guest Jackie Kashian, the only guest whose humor does not, on some level, focus on making people uncomfortable. Kashian, Holmes, and Andre have fun with racism and stereotypes in bits that riff on racism in ways that sometimes border on offensive.
Things don’t really take a turn for the deeply uncomfortable until Glaser comes on. Holmes has a tendency to talk a lot, particularly when he’s anxious, and his talk with Glaser kicks off with Holmes asking Glaser lots of strange questions that he then follows up with other strange questions before Glaser has an opportunity to answer.
In rapid succession, Holmes asks Glaser, “Sex comes from our parents, don’t you agree?” followed by, “I think everyone’s a little bit gay. Would you agree with that?” and “Are you introducing (your son) to any gender issues?” Glaser does not answer these question and you can all but see the tense expression on Glaser’s face as he does not respond to Holmes’ manic flurry of questions and jokes and riffs and foolishness.
There is a profound tension on the podcast even before Holmes mentions that he learned that he had scored the lucrative if not terribly prestigious Etrade commercial gig from Glaser after Glaser nearly scored the job himself. Glaser, to put it mildly, is not particularly amused that Holmes chose to share this trivia with the audience.
In fact, it would not be too much of an exaggeration to say that this faux pas makes Glaser legitimately angry, although again, it’s hard to delineate how much of that anger is genuine and how much of it is an act. Glaser would be entitled to be annoyed at having a professional rejection brought up for no discernible reason except that it might spark a funny anecdote, and his anger, real or imagined, lends a dark energy that lasts through the end of the show.
Glaser is followed by another comic genius as prickly and unconventional as he is brilliant: Brett Gelman. In the early part of the conversation, Gelman seems uncharacteristically earnest, but it’s tough to figure out whether he’s being genuine talking about his childhood and early dreams of being a performer, or whether it’s another bit and he’s actually doing a meta burlesque on the concept of mawkish sincerity.
But things don’t get Jon Glaser-level weird with Gelman until Andre throws out a call-back involving Morgan Freeman’s sexual relationship with his much-younger ex-stepdaughter. This pisses Gelman off and the rest of the podcast travels such a strange, rocky path that Gelman compares it to a wound that has been healed, and then ripped open, and then healed, and then ripped open again.
That is an apt comparison and this extra-weird, extra-uncomfortable podcast episode is like a wound ripped open, but, you know, in a good way. Or at least a weird way.
Nathan Rabin is the former head writer of The A.V. Club and the author of four books, including Weird Al: The Book (with “Weird Al” Yankovic) and, most recently, You Don’t Know Me But You Don’t Like Me.