Eddie Pepitone, Sean Conroy, Jamie Flam, and Amber Kenny discuss their favorite episodes of The Long Shot Podcast

Bestcasts asks podcasters to discuss the three most memorable episodes of their podcast.

The podcasters: Most comedy podcasts understandably bring together like-minded souls (in the case of Sklarbro Country, it brings together folks who have been collaborating as far back as the womb), but The Long Shot Podcast thrives on a diversity of voices. The rollicking podcast assembles the disparate but complementary sensibilities of fiftysomething professional kvetcher Eddie Pepitone; stern fortysomething comedy taskmaster Sean Conroy, who is a gifted improviser, comedian, and writer for Key & Peele; thirtysomething everyman Jamie Flam, a comedian and producer whose meandering anecdotes and self-improvement goals are rich sources of humor on the podcast; and ebullient comedian Amber Kenny. Over the podcast’s six seasons, listeners have followed Pepitone’s unlikely but richly merited rise to cult stardom and the making and release of The Bitter Buddha, the documentary about his life; Flam’s efforts to find himself creatively and purify himself spiritually; Kenny’s evolution as a performer; and Conroy’s enduring attempts to hide his frustration and annoyance with the world in general and his Long Shot compatriots in particular. Pepitone’s travels have taken him away from the podcast with increasing frequency as of late, but no matter the lineup, The Long Shot Podcast remains a consistent delight.

Episode #411: “Chuckie’s Christmas Episode”
Amber Kenny: I feel like it was the beginning of a trope of Jamie having classic stories that start off harmless, and maybe even wholesome, and have a tragic twist that we did not see coming and find hilarious.

Eddie Pepitone: Hi! This is Eddie Pepitone. [Amber laughs.] And I think what was particularly funny about Jamie and the dead dog story was that it was a Christmas episode. That made it even more devastatingly inappropriate. With Jamie, what really rings true and what hits home are how inappropriate his emotions are. Like, we’ll all of a sudden be talking about something light, and he’ll talk about something so heavy that it’s funny.

Sean Conroy: Why is that inappropriate, though? Who said it was totally inappropriate? [Laughter.] I think what’s funny about it to me is that Jamie never has any stories, and then finally he got excited about a story about himself, and it was about the death of his dog on Christmas.

AK: The theme was “Christmas,” and that was the only crucial story that came to mind! [Laughs.]

SC: It was the most wonderful time of the year, but for him it was about the death of his dog.

Jamie Flam: But I’m a Jew. [Laughter.]

SC: That is to your credit.

AVC: Although with Jamie, it seems like the criticism he receives is that his stories don’t go anywhere. It’s not that they’re inappropriate, necessarily; they meander on a route to nowhere. But that particular story had a very dramatic ending.

JF: It totally had an ending, and that’s what made it so funny to me. Because as soon as we started talking about it, I knew the end of it was that the dog was going to die. But the ending was so final and horrific that it was one of those endings where a comedian will say something to an audience, and no one has anything to say, and they might as well file out. It felt like it was truly the end of the podcast as we know it.

SC: And then when he was done, he shrugged and made a face at himself. As if he didn’t know what he was talking about, which I agreed with because I didn’t know what he was talking about. [Laughter.]

AVC: One of the other great things about “Chuckie’s Christmas” is the mental image of Chuckie committing suicide. For some reason, it’s reminiscent of the first A Star Is Born, where the male protagonist commits suicide by walking very slowly and dramatically into the ocean. It brings to mind Chuckie, the dog, killing himself in the same dramatic way.

SC: Yeah. Except I feel like in our version, Chuckie was a hapless victim of circumstance who was so sad about the fact that Jamie wouldn’t play with him on Christmas. The Lakers were on, and Jamie had a burrito because he’s a Jew. [Laughter.]

JF: It also led to a lot of character play. I think we started imitating the dog, which was a lot of fun.

AVC: 1950s-style animal characters seem to be one of your specialties, Eddie and Sean.

JF: Well, I do like to give my animal characters an Edward G. Robinson bent, if that’s what you mean. I don’t do much animal impressions work, but if I did, I think I’d have much more of an ’80s approach.

AVC: What would your 1980s version of an animal be?

SC: [Laughter.] Go ahead, Jamie! Do your ’80s impression of an animal!

JF: [Does ’80s camel voice.] This is an ’80s camel: “This is a cool party, guys!” [Laughter.]

SC: There was nothing either ’80s or camel about that.

JF: [Makes camel sound.]

SC: Now that sounds like a fucking camel!

JF: I just did the camel, then! [Attempts again.]

SC: That’s what a fucking camel sounds like. Again.

JF: [Attempts camel again.]

SC: Goddamn it, I want to go for a ride! [Laughter.]

AVC: Sean, do you think it would ruin the dynamic of the podcast if you were ever to enjoy any of the characters that Jamie does?

SC: Are you asking me that? Sean.

EP: Or me, Eddie?

AVC: Both.

SC: It wouldn’t ruin the dynamic of the podcasts if I enjoyed Jamie’s characters at all. But I do enjoy not enjoying them. [Laughter.]

EP: I think listeners have come to love the fact that Jamie’s stories go nowhere and they love the reactions the three of us have to it.

SC: Could you enunciate?

EP: I don’t know why I’m talking like this! I just feel like the listeners have come to enjoy all of the reactions to Jamie’s stories not going anywhere and us beating Jamie over the head with a baseball bat, Amber defending him, sort of, and then Jamie kind of justifying it. It’s a lot of fun for people.

AVC: Actually, that brings us to the next point. It might have been in the “Chuckie’s Christmas” episode or the “Animal Bank” episode, but it was you, Eddie, who was taking Jamie to task for not having a point of view—for his point of view being boring. Don’t you think, at this point, he’s found a point of view? Or has that defined him in the context of the podcast?

EP: Are you saying that the fact that he doesn’t have a point of view is his point of view?

JF: Holy fucking shit! [Laughter.]

AVC: That’s been one of the dynamics kind of going through all the seasons:  Jamie finding himself through trial by fire, by you guys challenging him.

EP: Yeah, I actually think that’s true. I’ve been on the road a lot, and a lot of people will approach me and say how much they like Jamie, and I think they identify with Jamie’s horrific struggle with life. [Laughter.] No, a lot of people listen to the show and go, “I am also floundering.”

AVC: But don’t you think that people identify with that? With that searching for your place in the world, searching for your point of view, for your lot in life?

EP: Yeah, that’s true. What’s difficult, I think, is as a comedian you really have to have a strong point of view and commit to things and I think that’s where we’re coming from when we get angry at Jamie. When you’re a comedian, you have to sink or swim in front of people by choosing a point of view. So I’ve always been someone who commits. Sometimes I don’t have anything but I’ll still commit, so it’s just a weird thing to hear someone who is so non-committal. [Laughter.]

JF: I’d just like to point out that Eddie, once again, finished talking, then made a huge face to himself, like, “I don’t know what the fuck I’m talking about.” Over the course of six seasons, that first season, there was no point of view. But now, there is.

EP: Do you see what I mean? [Laughter.] Now that Nathan is saying he has a point of view, Jamie can’t commit to actually saying that exact thought.

JF: Don’t include this in the article.

EP: [Laughter.] Please do. Do whatever you think is right.

AK: Do you.

SC: Follow your heart. I think that’s what people relate to is that every five minutes, Jamie is like, “I’ve finally figured out how I’m going to make my life better. I’ve finally found what’s going to make everything better.” I think that’s a very real thing that people do. “I’m going to go on this diet, I’m going to start working out, I’m going to eat healthier, I’m going to stop smoking, I’m going to stop having so much sex, or I’m going to keep having just as much sex.” But Jamie does that almost every episode in one way or another, and I think people like that.

EP: I think I get so mad at Jamie because he reminds me of the worst part of myself. The part of me that won’t follow through on things.

JF: I do follow through. [Laughter.]

[pagebreak]

Episode #313: “Hiking”
AK: More animal characters. [Laughter.]

EP: Now that’s funny because Amber works in a bank. I forget how that came up.

AK: It was a story because I was a teller and I was telling.

SC: It was a stupid pun on my part.

AK: And I said that my dogs went down a bank.

SC: And I choose to interpret that as her dog going to a bank. Which is hilarious if you think about it.

AK: It was this story about Domino, my childhood dog, which I still, and this is going to sound completely insane, but I miss that dog. It was really, really special.

AVC: What kind of dog was it?

AK: It was a Dalmatian, and I’ve had fans who have drawn Domino because of “Animal Bank,” and it’s been really, really, really cool.

EP: The most fun I have on the podcast is when Sean and Amber and me—and sometimes Jamie—get into silly riffs. Because one of my problems in doing a podcast is that I think that everything I say has to be so important and deep. And in a silly way, I realize, “Oh, shit. My job is to be funny and have fun.” It’s such a cliché in the comedy business for everyone to tell you to have fun, so when it actually happens, it’s such a relief. When I’m feeling why I got into comedy, which is…

JF: …to be funny. [Laughter.] We’re all rich, by the way.

EP: We’re filthy rich, Nathan!

SC: I think one of the things, for me, that stood out about that particular moment, which I think was pretty brief, was that “Animal Bank” riff is not that long.

EP: But we keep going back to it.

SC: If I may finish my point, the thing I really liked about that was that it was just us being silly the way we are in real life, and I really felt that for the first time in the show where we really tapped into that thing. And this is no offense to Amber or Jamie, but there’s this silliness for Eddie and I because we’ve been together for almost 20 years at this point, and to be able to access that on the show, I thought, “This could be fun to do on a regular basis.”

AK: So offended.

AVC: Sean, you and Eddie are sort of a unit unto yourself because you have so much history together, and because you have your own improvisation background. Is it difficult to integrate the unit of Sean and Eddie into the quartet of The Long Shot Podcast?

EP: I feel unqualified to answer that.

SC: He’s saying is it hard for us to integrate with these guys into the podcasts.

EP: Not anymore. I think, like any process, it took a while. But I think me and Sean hook up immediately.

SC: And then kill it. How do you feel about that, Amber?

AK: It’s interesting listening to older episodes because it’s so clear my part and my contribution to the podcast, but you can hear me getting more comfortable as time goes on. At the beginning, you can definitely hear that you guys have experience and you have confidence, and it was intimidating. Also, you were doing great, so no need for us to throw stuff in. But I feel as time has gone on, I’ve figured out where I make sense with you guys. Oh, man. Did that sound so pretentious?

AVC: It wasn’t pretentious enough.

AK: Okay. I’ll rewrite it. [Laughs.]

EP: And Jamie says he’s still looking for his rhythm. I don’t know if you caught that.

JF: I’ve found my role.

AVC: You don’t think that at this point you’ve found your role or your rhythm within the show?

JF: I’ve learned that most of the time I’m going to say what I’m going to say and not everyone is going to think it’s funny, but I’m just trying to make myself laugh. I contribute stories that will be fodder for these guys to have fun. And, of course, do my famous characters.

AVC: What was your original vision for The Long Shot Podcast when you were still conceptualizing it?

AK: Well, originally wasn’t it supposed to be about people who weren’t making it?

JF: We almost had an idea for the show—that it was supposed to be a show about how much it sucks to be in Hollywood and not be achieving anything, and then we thought that’d be a bad direction to go.

AK: That’s still exactly what we’re doing. [Laughter.]

SC: I don’t know if we had a clear idea except that we’d get together and sort of have conversations that other people might enjoy listening to.

AK: We had one pilot episode. The “Cookies” episode is what we call our pilot episode, but we have a pre-pilot episode where it’s just the four of us, and it is awful.

EP: I’m, like, addressing the nation like Franklin Delano Roosevelt.

AK: We were talking in weird British accents, and we were all meandering and talking about nothing.

EP: We had no structure.

AK: And we were all so aware of the microphone.

SC: But then I think we listened to that and thought, “Okay, we need to have a structure for the show.” I’m a bossy person, and I was like, “We need to do this.” So we sat down and hammered out this structure. We also talked about rotating the hosts to lead the discussions, and I made sure that discussion didn’t last long because I wanted to be in charge. Two things: I think one thing is that I am a control freak and I always have to be in charge of everything. That’s a part of my personality that I’m not a big fan of, but it comes across in a way that I have set this all up so I can say, “Okay, let’s move on and talk about what we’ll talk about next.” Then the other thing is that it goes back to the thing I have with Eddie, in that he’s just a whirling dervish who could spiral out of control very quickly if there’s not someone there to handle the reins, so to speak.

AVC: Do you think your background as a teacher informs your role on the podcast?

SC: Yeah. I think, unfortunately, a lot of me comes across still as a junior high school teacher. [Laughter.]

AVC: Well it does seem like when people aren’t paying attention, that bothers you in the same way a junior high school teacher would be bothered by people not paying attention.

SC: Yes. Absolutely.

AK: That’s very observant.

JF: I thought Sean’s teacher-ness really came out in the “Charred Glass” episode. Did you hear the “Charred Glass” episode? Sean was like, “Look, we have a structure.” And I was just so thrilled that Todd burst in and Sean was like, “Look. This is what we expected.” I could never impose that kind of discipline.

SC: It’s hard living your entire life disappointed.

[pagebreak]

Episode #303: “Arts & Crafts” featuring Bill Burr
EP: I was just so impressed because I had never talked to Bill that intimately or that long.

SC: To backtrack, we had technical difficulties that day with this hard drive, and we had to reboot it. It took an extra hour and a half with Bill sitting in our living room. “Our” living room. We at The Long Shot share a space. [Laughter.] Bill was in our living room for a couple of hours before recording the show.

AK: And we were talking the whole time.

SC: Yeah, we were just shooting the shit with him the whole time, and we really were able to get into some stuff. [To Amber] Anyway, go ahead.

AK: We easily could have ended up running dry before the recording started, but that wasn’t the case at all. He was like an unending well.

EP: During that episode, the topic was arts and crafts, and I was saying you could always tell a failed actress because she’s selling crafts on the side of the road, or jewelry. And Bill said to me, “Hey, it’s ridiculous to call anyone a failed actress because it’s like winning the lotto.” He was so positive. He started this whole rant about not getting down on yourself about being a failed anything, and this is a really tough business. Instead of feeling like a failure, he’d give himself a talking to and do certain things, and it inspired me not to be such a miserable fuck.

SC: It worked out great!

EP: And I loved it. I loved how inspiring it was because Bill is this blue-collar guy—

JF: But he had a white collar on.

EP: [Laughs.] Right, right. Yeah, yeah.

SC: But the one thing he talked about, and this kind of goes hand in hand with what I was saying and was also inspiring, was don’t let other people tell you what you can and can’t do. Just do your own shit. He had just made this movie with Joe DeRosa and… I forget who else.

EP: DeNiro. No, Pacino. Actually, he did do a movie with Pacino and [Christopher] Walken.

AVC: Stand Up Guys was a terrible, terrible film, but at a certain point you go, “Hey, it’s Bill Burr!”

SC: But his whole thing was, “Make a movie, do a thing.” Never let someone come up to you and say it’s okay to do this because those people don’t know what the fuck they’re talking about anyway.

AVC: It’s interesting that he’s the only guest of the three episodes you suggested. Does the podcast feel a little purer when you don’t have a guest?

SC: Like our little dysfunctional podcast family gets to flower? I think that’s absolutely true because when we have a guest, and depending on who it is, Eddie might have a relationship with them that the rest of us don’t have, or Eddie and I might have a relationship with them that the rest of us don’t have.

EP: Or I try and impress them.

SC: That’s often the case that Eddie’s trying to impress the guest, and that changes his personality. [Laughter.]

EP: The more famous they are, the more I try to impress them.

AK: Going back to my pretentious metaphor, it’s just another person in there who might not have our specific rhythm. We have our dynamic, and it works together pretty well now. Adding another person doesn’t screw it up, but it’s just sort of…

JF: Different.

SC: That was Jamie Flam, by the way. Jamie Flam.

“Dog Shoes” (Bonus track comedy song about shoes for dogs)
JF: I feel like I’m being ambushed. [Laughter.]

AK: I was just jonesing to talk about “Dog Shoes” again.

EP: Well that episode signifies Jamie’s high watermark, I believe. I think we were just so floored by the song itself.

JF: I had this idea in my head that they weren’t going to know what it sounded like until it was done, so I was trying to get some sort of trust to know if they thought it would be funny. It was a long night, and everyone was so exhausted and delirious.

AK: I feel like that was a notable episode for me because it was the first time, with maybe the exception of Jamie, where the three of us laughed together as friends and it was a real bonding thing. That sounds so cheesy. [Laughs.]

EP: I had no idea what the fuck was happening or what Jamie was talking about, and I think that’s why it was so funny. I don’t know if you ever listened to the “Making Of ‘Dog Shoes’,” but it was just laughing at how absurd what we were doing was.

AK: We couldn’t get through it.

AVC: It seems that originally, skits and songs were part of the vision for the podcast, but that has fallen away over time.

EP: Yeah. We’re kind of bummed out about that, actually. Or I am. Because I liked the little sketches, but they have fallen by the wayside.

AVC: Do you think it’s just not worth the effort?

SC: I don’t know. For me, it was when we’d just pitch ideas to each other, and it’d get so stressful. I like sketches to be funny.

JF: Sean’s always a taskmaster when it comes to sketches.

SC: Those were some of the biggest battles on the show because there were some moments on the show where our discussions would turn into a fight between an abusive couple in front of their children. Eddie and I—well, Eddie—would be screaming at me, and I’d be talking to him very reasonably [Laughter.], and Amber and Jamie would be cowering in the corner like, “Is this something we did? Is this our fault?” So that is one of the reasons that fell by the wayside. I could have handled those situations better, but what are you going to do? You’ve got to move on.

AK: Are we never going to do sketches again?

SC: We might.

AVC: With “Dog Shoes,” it seemed like the most brilliant thing or the single most stupid thing anybody has ever done.

JF: I’ll stay on “stupidest.”

EP: But that’s what was most fun about it for us. It was so ridiculous that it was fun, if that makes any sense.

AVC: Well, there was a sense of joy that comes through in that episode.

EP: Yeah. Didn’t we make a “Making Of ‘Dog Shoes’” where we were all cracking up for half an hour?

AK: Oh, man.