Episode 30 — FREEWAY ROSS DOUTHAT Pt. 2: Tha Harvard Plug

“I skimmed almost the entire thing” sets off the longest Chapo Reading Series entry to date. The Reading Series is the essential appeal of Chapo; the MST3K-style concept gives the Dry Boys plenty of room to crack jokes at the expense of awful pundits, the show’s favorite targets, but also provides jumping-off points for dissections of conservative pathology. Ross Douthat’s memoir of his time at Harvard was too perfect a subject to pass up, and it’s at once one of the show’s most focused episodes and its most relaxed. Brendan, whose soothing diction rounds out the group by countering Will, is the show’s secret weapon, balancing the usual group dynamic of Will managing Felix and Matt’s different flavors of leftist invective. The show’s since expanded its cast of co-hosts to include Amber and Virgil, jumbling group combinations week-to-week, but the groove struck in this episode was a kind of magic.

2. Episode 27 — Tomorrow Belongs To Them feat. @Bro_Pair

I listened to this at least twenty times in the run-up to the general and haven’t since. Not quite as laugh-free as advertised, but packed with insights into The Zone delivered by America’s most prescient and scandalously under-employed political pundit.

3. Episode 59 — Tell Your God To Ready For Chud

If there’s anything like a controversial placement on this list it’s picking this premium ‘sode instead of the blockbuster “We Live In The Zone Now” that ran a few days prior and served as post-election decompression for tens of thousands of new listeners. But this roundtable breakdown of failed Democratic strategy, featuring guests Matt Karp and Connor Kilpatrick along with new host Amber A’Lee Frost, showcased a sprawling new group dynamic (dubbed “Chapo Season 2” by Will) and burrowed into the intra-left conflicts that would dictate a new way forward. Demerit: Karp and Kilpatrick’s voices are virtually impossible to tell apart.

4. Episode 17 — The Road To Soavedom feat. @robbysoave

Is this episode super fun to revisit? Not quite, but it’s an early instance of the boys putting their money where their mouth is, a “hostile guest” invited on as a thin excuse for an episode stuffed with audio-distorted Cushbomb rants. Robby “entire body made of cartilage” Soave gets points for calling in to meekly agree with everything Matt said.

5. Episode 42 — Uber for Ubermenschen ft. @nkulw and @edzitron

With often loose preparation and a reliance on improvisation, the best episodes of Chapo rely on the hosts all bringing their A-game. Here a new audio set-up seemed to bring with it a new sense of energy and direction as the show tackled Silicon Valley, a hotbed of gussied-up capitalism populated with a massive host of new characters for the Chapo canon, most memorably Elizabeth Holmes as impersonated by Felix. The “Killer App” sketch and brief fusion with the Scumbag! podcast round out an episode in which everything seemed to work as it should.

6. Episode 15 — Alligator Tears feat. @Roqchams

Featuring the show’s “Cronkite/JFK” moment in Roqayah Chamseddine reading the Brienne of Snarth alligator tweet to the boys for the first time, this episode is also one of the show’s best discussions of a single topic, in Roqayah’s critique of “bougie feminism”, a subject the show would return to. One of the show’s best guests, Roqayah’s podcast Delete Your Account is similarly essential listening.

7. Episode 13 — Justified But Woke feat. @ckilpatrick

In the early days of the show the boys hit a groove with a series of episodes on a winning formula: a single guest and an extended interview/discussion segment that took up most of the episode. Connor really seemed to spark with the group and the result is one of the show’s funniest hours, mixed with acerbic commentary on the last days of the Sanders campaign.

8. Episode 12 — Love That Ron feat. @virgiltexas

Ron Fournier looms larger in the Chapo mythos than any other pundit, and this early episode lets future host Virgil, along with Felix, take control of the hour.

9. Episode 65 — No Future ft. Adam Curtis

Curtis skeptics might have a hard time with an episode in which his voice is allowed to almost completely dominate the conversation, yet his fertile imagination leads the episode into some fascinating directions, analyzing the show’s usual complaints about liberal ineffectiveness through a history of science fiction literature and specifically cyberpunk. And for a show whose hosts are often accused of talking over guests, the final minutes of Curtis’s segment are the product of savvy interviewers.

10. Episode 11 — Cranking the Donkey feat. Matt Taibbi

Tha Bruenig Ultimatum, Barbara Boxer and the dildo RPG, Kevin “Fat Dracula” Williamson, inside commentary from the most Chapo-friendly of America’s veteran campaign journalists: it was all here in the show’s first great episode.