Before Eddie Pepitone Said Goodbye to ‘The Long Shot’, They Produced a Stellar, Super-Sized Episode

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Like a lot of people, I was initially attracted to The Long Shot podcast because of Eddie Pepitone. I had become a fan of Pepitone through his appearances on WTF. I was fascinated by his contradictory persona, the way he alternated between righteous rage and surprising tenderness, between explosive cynicism and hard-won idealism. Pepitone has the ingratiatingly old-school sensibility of a politically active dock worker — the kind who would head up his neighborhood’s union — albeit one who is perversely obsessed with how his Twitter account is doing.

Pepitone was the podcast’s star attraction. He was its marquee name. I, like many people, came to The Long Shot for Pepitone but I quickly fell in love with the podcast in its entirety. Pepitone surprised few by leaving the podcast so he could start his own (Pep Talks) a few years back, but The Long Shot is just as good now as when Pepitone was a regular, and at times even better.

Without Pepitone’s manic comic energy, the personalities of the other podcasters emerged more strongly, particularly that of Jamie Flam. If Pepitone is all rough edges and gruff urban energy, Flam is perhaps the least cynical person in all of podcasting, and outside of it as well. In a podcasting and comedy realm where sincerity is often seen as a weakness, or an inducement to mockery, Flam has the courage to be nakedly sweet and earnest and sincere in his life’s goal to spread “enchantment,” both as a performer and a conceptual mastermind.

Flam’s lack of cynicism is even more remarkable considering that he works as a booker at a legendary comedy club, which is the kind of gig you would imagine would kill anybody’s faith in humanity. Yet Flam has managed to maintain his hippie-style mellow despite having this most stressful, and least chill, of day jobs.

Pepitone’s absence has similarly highlighted the strength of Sean Conroy, a veteran standup, improviser, and writer who has never lost the stern, commanding air of the teacher he once was. The initial novelty and appeal of The Long Shot is that it was a podcast featuring four very different people, but Pepitone and Conroy, both men of a certain age who have lived very full lives, functioned beautifully as a unit onto themselves.

Conroy and Pepitone have the kind of comic chemistry that only comes with age, time and experience. They are wonderfully complementary talents who, in 2013’s standout “The Longest Long Shot Episode Episode,” repeatedly lock onto a bit or a tangent and glean big, ridiculous and sustained laughs out of it. They’re particularly adept at essaying the characters of Al and Margaret, a clueless old couple, and inhabiting the personalities of dogs, including a dog that, in a particularly brilliant bit, also works as a doctor.

The episode is notable in part due to its length, but also because it features both Pepitone, who wouldn’t be on the show for much longer, as well as Joe Wagner, a comedian, writer and fan-favorite guest who would go on to be the show’s fourth podcaster. To put it in Kiss terms, this episode is like having an opportunity to see Ace Frehley and Tommy Thayer perform on the same stage, only even funnier!

Conroy runs a tight ship, but the best Long Shot episodes tend to feel loose and weird and ramshackle and self-indulgent. Accordingly, “The Longest Long Shot Episode Episode” doesn’t even get to special guest Joe Wagner until forty-five minutes in. The show has more structure than most podcasts, thanks to regular segments like “Checking In,” and “Parting Shots,” as well as loose themes, but the best parts of the “Longest Long Shot Episode Episode” generally have very little to do with the themes and more to do with hilarity created in the moment.

Conroy’s eternal irritation with Flam’s character work — basically all of Flam’s characters sound the same, and they all seem like they could have been the product of the imagination of a middle-school class clown with ADD — has long been a running gag on the podcast. Conroy and Flam have a dynamic that at time recalls that of Walter White and Jesse Pinkman during the early days of Breaking Bad, before White evolved into a super-villain of Lex Luthor-level proportions, with Conroy as the eternally disappointed, stern, and irritated father figure and Flam as the eternally disappointing protege.

As Conroy acknowledges in the episode, Pepitone’s commanding presence has a way of keeping Flam’s goofiness in check. Flam wouldn’t really come into his own on the podcast until after Pepitone had left, and Flam recedes into the background for much of this particular episode.

The Long Shot is a comedy podcast but it’s also, in no small part, about four engaging souls trying to figure out their personal and professional lives, and where they belong in the crazy-making world of show-business. It’s about comedy but more importantly it’s about people, and that comes through in “Longest Long Shot Episode Episode.”

Just as Conroy and Pepitone work beautifully as a team within a team, Flam has a contemporary in Amber Kenny, who similarly seems far too nice, sunny and positive to even be in a dirty, soul-crushing business like standup comedy. Part of the show’s arc has involved Kenny finding herself and her voice as a comedian and comedy dancer with her troupe Liquid Feet, and this wonderful episode finds her and Flam in fascinating points in their personal and professional journeys.

I recommend starting at the beginning of The Long Shot and tracking this underrated and beloved podcast’s ascent from its first episode, but this episode is a terrific place to start as well. It illustrates both what Pepitone brought to the podcast as a singular talent and why the show was strong enough to not only survive but flourish without him.

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.

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