The show spun off of Podtoid, the official podcast of the video game website Destructoid, which was hosted by the trio from 2011-2013. Although its subtitle was "Destructoid Video Game Podcast", the show gained a reputation for having jack-all to do with video games, instead focusing on the offbeat personas of the crew. When Jim left Destructoid in November 2013, The Dismal Jesters was created so the ball could keep rolling.
The format of the show is, essentially, completely undefined; the hosts crack jokes about whatever's on their mind, though Video Games are a frequent topic (all three men being professional games journalists) and Jim's extremely twisted sense of humor often sends the discussion in really weird directions.
The show can be found on iTunes or in an archive located here.
See also Jimquisition, Jim's weekly video show.
In early 2019 the cast got back together and started Boston's Favorite Son, a spiritual successor where Jim and Conrad suggest ways to make Jonathan famous again whether he wants them to or not.
This podcast contains examples of:
- Ambiguously Brown: Jonathan's never really mentioned his ethnic background, but he is indeed "brownish", leading to occasional remarks on it.
- The Artifact: On occasion, Jim will become annoyed if the conversation turns toward video games, and try to avoid it by singing a random song or some such. This joke is a holdover from the Podtoid days, where he would do so in an attempt to avoid talking about video games for as long as possible, even though it was ostensibly a video game podcast. Since Dismal Jesters officially has no main subject, there's not as much humor in his attempts to avoid the topic, so he doesn't pull that gag nearly as often.
- Blatant Lies: Jim claims that Trent Reznor has his phone number and is always texting him weird, annoying messages.
- Butt-Monkey: Poor Jonathan puts up with so much.
- Catchphrase: Jim's "Now hear me out, Jonathan!" and "Right?" whenever he's trying to persuade Jonathan to do something naughty. Jonathan frequently responds with "No! Why would I do that?"
- Deep South: Jim is English by birth, but he lives in Mississippi, so all the usual stereotypes get mocked every so often.
- Fan Community Nickname: Jim has suggested "Dickheads", or for especially dedicated fans, "Stupid Fucking Dickheads".
- Letters to the Editor: The Jesters answer questions from their Twitter followers in the last portion of the episodes. They tend to take these more seriously and honestly than the rest of the show, though they'll still give sarcastic answers if the question ever calls for it.
- Nice Guy: Jonathan plays this role on the podcast, and is one in real life too. He works at a psychiatric hospital and is known for his friendly and welcoming demeanor.
- Porn Stache: Conrad's moustache is beloved 'round the world. Truly, it's a sight to behold.
- Psychopathic Manchild: Jim's online persona is this, taken to the extreme. He's a nice guy in real life, mind you.
- The Quiet One: Conrad is a bit less talkative than Jim or Jonathan, only speaking up if he has something especially funny or interesting to say.
- Real Song Theme Tune: "Freakout" by Chainmale. They didn't get Chainmale's permission to use the song, so each week at the end of the show, Jim thanks him "for not suing us."
- Running Gag: Many, some to the point where they're basically regular segments of the show:
- "Willem Dafoe Movie Pitches", ideas they've come up with for a movie that would star Willem Dafoe. Usually these ideas are completely insane, and Dafoe's hypothetical character is frequently a play on his over-the-top Green Goblin persona. According to Jim, the gag is poking fun at how Dafoe seems willing to do absolutely anything in any movie, no matter how strange.
- The guys send a message to some company, asking them to sponsor the show. Their letters are always totally nuts, and it's clear that they're not actually expecting a response. Miraculously, every time they've sent a message, they've actually gotten a sponsorship!note
- Jonathan is forced to read a product description for a sex toy. Usually he reads them in a dry, bored manner.
- Jonathan's supposed alter ego (invented by Jim), "Freaky Constantina", who dances erotically to Usher's "Yeah" while wearing cut-off jeans and a mesh tank-top.
- Jim's obsession with actor Edward James Olmos. He's always coming up with new pitches for creepy TV shows that Olmos could star in, and has even said on a few occasions that he "can't stop thinking about him".
- The line "I'm don't really like [thing X], I'm just doing it for the power!", spoken in an impression of Francis Underwood from House of Cards (US).
- Spiritual Successor: Boston's Favorite Son, where Jim and Conrad suggest ways for Jonathan to regain his non-existent fame from his days on Road Rules, despite Jonathan's protests.
- Zany Scheme: Jim's always coming up with new ways for Jonathan to torment, humiliate, or jail himself. He never goes through with them, though, thank god.