Tom Scharpling?!?

What's a big star like that doing in a newsletter like this?

Tom Scharpling is best known for The Best Show, his long-running radio-party-cum-podcast. It’s hard to call him an “underground” or “cult” favorite — he was a writer on the USA Network show Monk for the duration of its run, and he’s the voice of Greg on the animated series “Steven Universe” — but I’d never actually checked out The Best Show until late last year.

Usually somewhere between two and three hours, the show runs live on Tuesday nights, as Scharpling and his producers take calls around a loosely-defined topic (like the controversial 50 Best Snacks). Whatever it is, the topic is just an excuse for Scharpling to offer his funny, curmudgeonly-but-kind riffs on the indignities and annoyances of daily life. Along the way, he displays his deep knowledge of rock music (he once published a music fanzine called EIGHTEEN WHEELER) as he waits for each show’s centerpiece: the call from Scharpling’s comedy partner Jon Wurster — drummer for The Mountain Goats and Superchunk, among others — who will be performing as one of the many annoying citizens of the fictional Newbridge, New Jersey or as the much-loved Philly Boy Roy:

I’d enjoyed dipping in and out of various Best Show debates (“Improve a movie by adding a dirtbike!” “50 Biggest Crabapples”), but I didn’t quite get Scharpling and his whole thing until listening to a 30-minute monologue he put out in lieu of a show back in February. He spent a good bit of time reflecting on creative struggles and his desire not to find himself at the finish line “with a pile of half-done ideas.” To acutally do something with ideas, he reminded himself of something a boss told him once: “ideas are cheap.”

This had everything to do with the things I’ve been thinking and asking people about here in the “How Do You Finish a Book?” section of A Saturday Letter. And so, when Scharpling said on a recent episode that, to promote his new book, he’d talk to any “nursing home newsletter with nine subscribers,” it was a perfect fit (It helps that A Saturday Letter has a tremendous open rate down at Our Lady of Perpetual Dentures).

The book, It Never Ends: A Memoir with Nice Memories, came out last week. In it, Scharpling tells the story of, yes, how he started The Best Show, and it has some great set pieces of the “why me?” variety — his awkward fan encounter with Patti Smith — as well as his strongly-held music takes — Nevermind is “Foghat being mopey;” My Bloody Valentine is overrated because they’re British. But Scharpling also discloses his mental-health struggles as a young adult — including his hospitalization and treatment with electroshock therapy — for the first time.

It’s a funny book with some hilarious set pieces as well as thoughtful reflection on the mental illness, creativity, and finding your way, and I was delighted to talk to Tom Scharpling about it.

And, not to toot my own horn, but I must say this is a master class in interviewing. Because what’s the thing that all the best interviewers know to do? That’s right: dominate the conversation right out of the gate to show the interviewee who’s boss. Watch and learn.

Go here to check out previous installments of “How Do You Finish a Book?”

Go to the About Page to learn more about A Saturday Letter.

How Do You Finish a Book?

No. 4: Tom Scharpling

The interview has been edited and condensed, both for clarity and to make me sound smarter.

Sebastian Stockman: You know, I heard you say on The Best Show you'll talk to anybody with a newsletter, so here I am.

Tom Scharpling: OK! Challenge accepted.

SS: I just finished the book today; I zipped right through it. And it’s really so much fun. You can certainly hear your voice in it. I know, uh, this is my interview of you, but I was hoping I could start by telling you a story.

TS: Of course.

SS: I'm sure you're going to get a lot of this sort of thing, but the Patti Smith story in your book — it sent me right back to this conference in Portland, Oregon. It’s like a literary/writing conference, and Colson Whitehead was the keynote speaker. Do you know Whitehead?

TS: I do. Not personally.

SS: Right, so each of his last two novels has won the Pulitzer for fiction and like, you know, he's a big deal, right? So it’s the morning after his address, and I'm waiting, in a Peet’s Coffee right across from our hotel. And who should be sitting there, but Colson Whitehead just by himself, just staring into the distance…

TS: Yep. Oh, I know where this is going.

SS: Right?

TS: It can’t go wrong. How could this go wrong?

SS: So I texted my friend. “Yo I'm over here,” you know? “And so is Colson Whitehead, and I’m trying to figure out, should I go talk to him or what?” And my friend's like, “Go talk to him.”

And so here's what I’m thinking: I had reviewed Whitehead’s nonfiction book, like seven years before for The Kansas City Star1. And he followed me on Twitter for a little bit, but then stopped. And then also I’d been hanging out with this guy, this sort of indie publishing figure who had been his college roommate. And so I’m thinking we have, like, a lot in common <laughs>.

TS: Sure, sure.

SS: And so I go over to him and I say, “Mr. Whitehead?” And, you know, I said some nice stuff and he stands up, talks to me, you know, lest I get the urge to sit down with him. And I said, “I actually reviewed your poker book couple of years ago, and then I was having beers with Richard Nash the other day… .” And he goes, “Ah, yes, my beloved Richard.” And so Whitehead is being absolutely polite but not, like, trying to keep the talk going, you know?

TS: Mmmhm.

SS: And so, it kind of peters out and then something grips me: I realize that I have been in this coffee shop, sort of glancing over at him and texting on my phone for like, you know, 20 minutes before going up to him, and now I'm going to go back over to the stool because I’m still waiting for my friend. And so I actually point over to the stool that I'd been sitting on, and I say, “I'm just waiting for a friend; I'm not stalking you or anything.” Like, a line from the worst sitcom, you know…?

TS: Yeah, it’s definitely not great to introduce the theme of stalking to a thing, because usually, a stalker would be the first one to say, “Oh no, I’m not…”

SS: And so he just says “I didn’t think you were,” implying that he might think so now.

TS: “...But now I’m reevaluating that claim.”

SS: That story is my way of saying that I had a number of moments like that — and I won't force you to listen to all of them — these moments of strong identification while I was reading. I also have been a sports writer and I've been in one or two life endangering car accidents, so anyway…

TS: Well, this is exciting. I found my target audience.

SS: Right! So, I do want to put on my English professor hat for a minute and note something that you observe and nicely summarize towards the end of the book, and that has to do with the problem of life writing, and you put very succinctly what a lot of academics spend articles and books discussing which is, basically, “what a weird thing.” It’s that a memoir or autobiography is not someone’s life, or not even the story of someone’s life. It’s a story of your life.

TS: Yes.

SS: One of the things that really launched The Best Show, you say, is when you opened up to the audience, and talked about how you were really feeling — but that was only up to a point, right? OK, so here's the question: did you “break” the story of your life? The way you do in TV writers' rooms?

TS: Oh yeah, well, look: everything is going to be performative to some degree, but this is much more open than I had been. When I decided to open up on the show, I opened up and started to own how I feel and [share] emotions and things in my life. But then there’s other things I've been pretty private about, and that’s where that’s at.

Then you strip another layer away and you get deeper — but you're never going to get all the way to the bottom. Because it turns, and suddenly you’re living in too-much-information land, and you're just an oversharer. It all needs to be curated or thought through to some degree, or it’s just going to be word vomit where I consider every part of my life equally interesting, which is not true.

SS: You say at the end of the book that you gave some of the more confessional chapters to your agent to say, like, “is this anything?” And if he had said, “yeah, this isn't anything,” do you think you would have done a different book or stopped the project?

TS: I definitely wouldn't have done this book. I might not have done any book. I needed to know that this worked and it didn't feel like a weird overshare or navel-gazing or any thing like that.

I trusted in what it was, but I still needed someone that wasn’t in my immediate personal life to tell me that it was something. So that’s what that process felt like: is this a thing?

And I probably would not have … I’ve always wanted to write a book, and I had entertained the idea of doing a book — a fiction thing, a novel-type thing or whatever you want to call it. And that’s kind of what I was aiming toward for a bit. And then it was like, “No, I think I’ve got to talk about this stuff and own this stuff and tell these stories.” I felt like I was finally ready to tell those stories, and so it was time.

“It’s going to be funny, and then it’s going to be sad and then it’ll get funny again, but the sadness will still kind of inform the rest of the book, unavoidably.”

A lot of people's memoirs are like a collection of stories, and there's nothing kind of linking one to the next. [But] I kind of felt like I could see a through line with it because of the heavier stuff in the book. And I realized I’m going to have to build the structure of this thing around these heavy things that ultimately have to be the anchors throughout, and then I can build the other stuff around it.

I say it in the book — it’s one of the earliest things I knew I was going to do: It’s going to be funny, and then it’s going to be sad and then it’ll get funny again, but the sadness will still kind of inform the rest of the book, unavoidably. But I kind of knew that was the general shape of it. As soon as I was entertaining [the idea], I kinda knew that shape.

So then it was about trying it and seeing oh wow, this works. This seems to be playing, structurally.

SS: Yeah. Well, that’s interesting. And I’m thinking about where — I am naturally drawn to the places in the book where you talk about writing — you call yourself a sucker for structure. But you also say, in a dig at Lorne Michaels, that “formula is for babies,” right2? Do you see those statements as contradictory? Or are “formula” and “structure” not necessarily synonyms for you?

TS: I don’t think they’re the same thing. I'm not being a slave to structure and following just some sort of dumb pattern that just makes a story reductive or pat, I'm not doing that3. Structure at its worst is when structure’s driving the bus of a thing over any other factor: quality, entertaining, interesting, funny, all that stuff [should be] secondary to structure.

SS: Structure is the thing you can play off of, I guess.

TS: I also didn’t want it to be some exercise in formless whatever, I wanted it to work and I wanted it to be tight. So it was trying to strike a balance between those two poles.

SS: So the ostensible subject of this interview series is, “how do you finish a book?” And I guess the question there is: after you showed those early chapters to your agent, did you go off and just try to write the whole thing yourself? Or are you showing things to people along the way?

TS: Well, part of the process is you write those chapters and so he’s like, yeah, this is a book…

SS: Let's sell it.

TS: Let's look to sell it. You showcase those chapters, and then you kind of pitch the general structure and say the kind of other things that will be in the book to inform and entice the potential publisher. I knew I had stories and events in my life that would work, and then started structuring them in the pitch document. And so I kind of knew like, all right, this'll be in it, this’ll be in it, this’ll be in it, and then a flow kind of starts to reveal itself.

I didn't want it to be super linear, I wanted to be able to move around a little bit and have it be more thematically linear, than just, like, chronologically linear.

And the arc that kind of revealed itself was the whole thing with the psychiatrist not remembering me.

“The end of the book just showed up, and I’m crying — for a week. That's just for better or worse, how it goes, if you're going to write about yourself and be kind of forthright and honest. That’s the kind of stuff you’ve gotta use.”

SS: Oh, man, yeah. [At the end of It Never Ends, Scharpling looks up the psychiatrist who’d treated him with electroshock therapy during his institutionalization. This indignity — that the psychiatrist who’d irrevocably altered the course of Scharpling’s life didn’t remember him, is a fitting — and traumatic — thematic coda.]

TS: When that happened, I knew. It was one of those moments where I was just like, this is the worst thing that ever happened to me — and that’s the end of the book.

SS: Totally.

TS: The end of the book just showed up, and I’m crying — for a week. That's just for better or worse, how it goes, if you're going to write about yourself and be kind of forthright and honest. That’s the kind of stuff you’ve gotta use.

SS: Yeah, it works! I mean, I know it was painful…

TS: One of the worst things that ever happened to me.

SS: But it does work structurally.

TS: But it was still fine. It’s the end of the book, and it’s one of the worst things that’s ever happened to me, and it’s terrible, and it’s a good ending for the book.

SS: Yeah, I mean, the idea that the guy who caused a bunch of your memory to get wiped out, had no memory of you, it’s just…

TS: If it was fiction, somebody would say it’s on the nose, and it’s a little too pat and convenient. But it’s like, no, it happened. What are you gonna do? Those are the facts.

SS: You are offering all kinds of stories you haven’t told before, but you do still hold things back. Your marriage, your private relationships, are still held pretty closely. Was that just how it worked or was that a thing you were being mindful of?

TS: That's a conscious thing. I'm telling certain stories from certain eras. And, you know, it's hard to tell a story you’re in the middle of. And there are other things that wouldn’t have fit in the book, and just also are not appropriate for what I was trying to accomplish in this.

SS: I mean, it goes back to that idea that it’s a story of your life, it’s not the whole thing, right?

TS: It’s not everything. Yeah. It's like, look, maybe the next thing, if I do another thing, that stuff, maybe I’ll cover it, maybe I'll never talk about it. It's just … such a strange thing, but you gotta pick and choose.

Because also, I wanted it to be funny! That was the goal going in the whole time: This book needs to be funny. Even with the sad stuff, I’ve gotta find a funny center to it, or the funny parts of the sad things.

The tightrope I was kind of walking with this thing was that I didn’t want to minimize anything that happened to me. I didn’t want to turn my life into a series of jokes where my pain is your entertainment. There’s some of that, but it’s not where it lives, I hope.

I wanted to respect the things that happened to me, and own what they felt like and how hard some of them were. I didn’t want to just be like “Ah, it’s all cool. Everything’s fine. What are you gonna do? That’s life.” No, some of these things really hurt and were scarring. So I wanted to acknowledge that, but I didn’t want it to feel like a “woe is me” kind of thing, I wanted it to be funny. So I tried to find ways to strike that balance as much as possible.

SS: And I think you do, and in the Patti Smith story or other things like that — where you are somewhat the butt of the joke, or the sad sack part of the joke — I feel like those are going to be the places where readers identify. Or some of us do, anyway. We’re not just laughing at Tom.

TS: Yeah, exactly. You’re supposed to be with me on it, even if you’re laughing at the circumstances. You’re not laughing at this buffoon. You know, you can laugh, but don’t laugh too hard. The worst version would be if somebody’s like, “Oh, look at this idiot, what’s this idiot gonna do next? He’s such an idiot.4” That’s not the goal. So, yeah, it’s a whole lot of striking of balances.

SS: Another balance —obviously you have a sort of built-in audience that you're hoping buys the book, and you're asking them to buy the book and stuff, but you also I'm sure want it to go out beyond the loyal Best Show audience. Were you thinking at times about how to explain The Best Show to people who haven't heard of The Best Show?

TS: I wanted it to be satisfying for somebody who knows the show. That they got things and stories behind the scenes or whatever that maybe they didn’t know, but I also didn't want it to just be inside baseball.

I tried to write it in a way that it’s open for people to get on board. If they don't know the show, then it's the story of a guy dealing with some problems, figuring his life out and having funny dopey stories happen to him in the course of him trying to figure things out and find his path.

SS: Yeah.

TS: And I feel like it works as that. I feel like they could fill in the blanks later, there's enough there that you could read it without being familiar with the show and get it.

SS: So just to go back, we talked about what you had to do to sell the book. But after you'd sold it and were writing it, did you lock yourself away and try to bang it all out that way? Or were you showing chunks to people along the way?

TS: I had a couple of people like my agent, and my friend Sammi Skolmoski was working with me the whole time and would read chapters. And then I would show them to the agent after taking her notes. I’d take the agent's notes and then just start putting it together that way.

“[T]his is the same shit over and over. And it’s shocking. The same thing can happen when you’re 14 and then it can happen again when you’re an adult.”

SS: Another intriguing thing in your book I noticed — and partly because I struggle with it — is that, in some areas you have a lot of confidence. Like when The Best Show is not taking off, but you know it’s good. But you also have a deep insecurity and a desperate need for approval, which I also have.

So, I found this theme that emerged that you didn’t talk about, but I wonder how much you think about that in your life, that — again, balance — between confidence and insecurity or desire for approval or…

TS: The conflict between confidence and lack of confidence?

SS: Yeah, that’s a better way to put it.

TS: It’s everything. It runs through everything. Just, I could be the most confident in one way and just a disaster in another way. And it’s shocking which ones flare up when they flare up. It’s shocking when I get a burst of confidence and I’m strutting around like the king of the world, and it’s just as puzzling when I’m plagued with terror. It’s unbelievable, and it just kind of is. It’s kinda the unfortunate part of all of this.

SS: Right. And… there’s no takeaway then, I guess. It just comes or it doesn’t.

TS: Yes, exactly, that’s exactly it. It’s just like, God bless ya, you don’t know which one’s going to show up.

[Excised interlude where I ask to ask him one more question just after I’d said there was a last question. He says “no, go ahead,” and then I spend more time apologizing than it would have just taken to ask the question. This is another pro tip for all the aspiring interviewers out there: Use at least 40 percent of your interview time apologizing for taking up the interviewee’s time.]

SS: When I have my students do personal writing, I ask them to notice what they are surprised by and what they've discovered. What was something that surprised you? You know, was there something that you hadn’t thought of that you remembered or rediscovered during the process of writing?

TS: One thing that really did tie into the theme of the book is where it's just like, this is the same shit over and over. And it’s shocking. The same thing can happen when you’re 14 and then it can happen again when you’re an adult.

And that was not just a convenient hook for the book; that was an absolute truth that showed up. Unbelievable. It’s stunning how these things change appearance, but at their core, they're the same thing.

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Thanks, as ever, to my hometown newspaper for misspelling my name in the byline.


“The final thing I would say is that The Best Show has been cranking for almost two decades precisely because we know when it’s time to retire an idea or a segment. You like formula? Well, guess what? FORMULA IS FOR BABIES. Now that is a burn! Imagine me dropping that xinger on Lorne Michaels in his opulent office before getting dragged into the streeets of Midtown Manhattan by his Broadway Video security goons with their one-size-too-tight Hot Rod T-shirts.”


I didn’t mean to say that it was!


This is where I ask Tom if I can use “Oh, look at this idiot, what’s this idiot gonna do next? He’s such an idiot.” as a blurb for my newsletter.