10 Questions

10 Questions with Jimmy Callaway

by Ryan Meehan

Jimmy Callaway is a stand-up comedian in San Diego, CA, where he’s a regular at The American Comedy Co. He spent his 20s and most of his 30s in punk bands and trying to get his novel-writing career off the ground before finally giving in to comedy’s siren song. However, his first novel Lupo Danish Never Has Nightmares will be available via Crime Factory Press this year. He has more comic books than you do, and he’s my guest today in 10 questions.

RM:  What was the first joke or set of jokes you told on stage that really hit; and what was so special about the feeling you got – other than a positive response from the audience – that made you really excited about writing more stand-up comedy?

JC: My very first set actually went really well, which was a huge, huge relief. My second set did not go nearly as well, but that was also something of a relief, since I knew I was going to have to eat shit more than a few times and I wanted to (and still do want to) get that out of the way as soon as possible. I think that relief was probably the most special about that feeling. One of the reasons I had put off trying stand-up for so long was because I was so very afraid that I was going to suck, and I couldn’t wrap my head around the notion that I was going to have to suck for a while. Obviously, that sort of fear stems from a real ego problem, but also I revere comedy so highly, I honestly could not bring myself to piss on its leg at all, even though (as established) it’s part of the craft. To sum it up in a corny way, stand-up was always something I wanted to do and the very act of doing it once cemented for me that I was not going to stop.

RM: You had the opportunity to work with Steve Agee and Rhea Butcher back in July…What was the best part about that whole experience for you; and what have you found that you can learn from watching talented comics that are nothing like yourself with regards to approach and subject matter?

JC: Pretty much everything, and that is the best part of the experience. At my level, there really isn’t anything I can’t learn. As far as things like stage presence or crowd work go, I pay very close attention to how these professionals do that and seek to implement whatever I can into my own act straightaway. But there’s a very real learning curve there, and as they have done, I will have to learn exactly how to do that just through years of practice. But also they’re just very nice people, to a one. There’s certainly varying degrees of such, but all the working comics I have met and have had the pleasure to work with have been very kind and fun people. So to know that you don’t need to be some sort of diva asshole to make a career for yourself as a comic is a relief and certainly something I aspire to. And it’s all very much a thrill, to work with people whose work I’ve admired for years, and it’s still very surreal. When Agee was here, I was initially going to host, but then he wanted to come out at the top with Mike Keneally and his guitar and do a couple quick songs, so he ended up hosting the show himself. And he asked me how I wanted to be brought up. And I say, “Oh, just something like I’m the house MC here,” but on the inside, I’m like, HOLY SHIT STEVE AGEE IS BRINGING ME UP. Crazy world.

RM: How would you best describe the environment that exists inside and around The American Comedy Company in San Diego? Why do you think that’s become a venue at which you’ve felt so comfortable developing your material?

JC: It’s an extremely fast-paced, high-pressure work environment, much more so than anywhere else I’ve ever worked by far. But the stakes are fairly high, so that’s just how it’s got to be. Even before I began working here and became, quite literally, a company man, I thought of the club as being the best in town by a wide margin, and maintaining that standing is not as easy as falling off a log. But that in turn creates a great environment for developing material, even if it’s raising my blood pressure through the roof. On top of that, everybody I work with is extremely supportive of my comedy and genuinely seems to enjoy it, even if they’ve heard some of these jokes over and over and over and over and over and over and over again. And then, of course, there’s the simple fact that I’m working in a field I love dearly, warts and all. For years, I worked menial, low-pressure jobs, figuring if I just had a job where I could punch in and punch out, I’d have time to pursue my creative endeavors. And I did, but the dreary grind of packing children’s books or social media consulting is more than enough to deaden any kind of creativity when it’s applied with its fullest force, even when one is determined to get out. Y’know, like quicksand. So, like I say, even though I have what can be an extremely worrying and stressful job, I wouldn’t trade it for anything right now. Though the bullet-in-the-head scenario still has its appeal on some days, but that’s pretty much standard when you’re me.

Callaway, under pressure on the job

RM: When I first contacted you about doing this, you referred to yourself as “an overrated open micer”…Do you really feel that way about where you currently sit with regards to your skill level at the moment, or is that more of an example of self-deprecation for the purpose of entertainment? If so, how much self-deprecating humor do you use in your act?

JC: A little from column A, a little from column B. I’ve only been at this for two years now, and I have come way farther than I ever really would have dared hope. I’ve caught some very, very lucky breaks, and I also work very hard on comedy. So, basically, I’m farther than I thought I would be, but nowhere near funny enough yet. I do also have a pretty large ego, and I feel it’s important to keep that in check, not just because it’s an attribute I find unattractive in others, but also for my own mental health. I guess my act has its fair share of self-deprecation, but probably not more so than most. If anything, my stuff seems to have more of a “Gee, aren’t I clever?” vibe. Which I’m fine with, even if I sometimes want to slap the smug look off my own face. Again, nothing new there.

RM: We live in this very bizarre world ruled by social media where we seem very concerned with documenting instances of interaction by using apps like Instagram, and that approach has really made me wonder if anybody is actually taking in the moment of being at an entertainment venue to see a show…Do you think that I might be on to something there; and if so how do you think that this trend is going to have an effect on the way stand-up comedy is performed in the future?

JC: Yeah, I’d say you’re probably on to something, but they said the same sort of stuff about TV and video games when I was a kid, in the Neolithic pre-internet days. I think at comedy shows in particular, most venues are invested in keeping people off of their phones or otherwise being distracted/distractions themselves, much less so than at concerts or movies or events like that. And I’m as glued to my phone as anyone else is, but at a show, I forget all about it and just am present. So I don’t really think live stand-up is any more danger than it was before smart phones were a thing. If people would rather be on their phones than go to a comedy show anyway, then fuck them, they’re the ones missing out. I used to rail against just this sort of thing myself, and I didn’t even break down and buy a cell phone until a few years ago. But really, it’s not social media that’s a problem; it’s just people being schmucks. Which is probably never going to end, so I try not to worry about it too much.

RM: Which of the following two scenarios is more troubling to you:  A comic who is getting away with being a hack that is fully aware of what he or she is doing on stage to get laughs, or someone that is achieving the same level of crowd response out of similar material who has no idea that what they are doing is hack?

JC: Again, my answer adds up to about a shrug. Hacky comedy is hacky comedy, and the intent behind it doesn’t really make much of a difference. If a comic sets out to do hack stuff because it gets a laugh and it’s working, then it’s hard to argue with those results. It seems like they’re “getting away with” something, I guess, but I dunno. It’s unpleasant to witness, surely, and can be seen as a detriment to good comedy, but the way I see it, nothing can stop good comedy, even if bad comedy is still hogging up market shares. If a comic is getting laughs because he or she is doing stuff that he or she truly believes in, yet it’s also hacky, then you still get comedy that you or I might perceive as unfunny, but people are still enjoying it and willing to sit through it, and hey, God bless. All one can really do is just whatever one wants. I try to do jokes that are not hack, jokes that actually mean something to me, and then hope that the audience feels the same way. If I’m hosting, I’ll fall back on standard banter to keep the show moving along, even though there’s usually a part of me that is kind of grossed out. Like, I did a bar show not long back, and the crowd was responding well to crowd work, so I did a bunch of that. When I listened back to my set, I was like, “What are these people laughing at, this guy’s a hack.” But then I was like, “Ah, fuck it, let’s go get a cheeseburger.”

Above: Not the actual cheeseburger eaten in aforementioned story

RM: Let’s discuss the novel for a second…Who is Lupo Danish; and how would you best summarize what the book is about in one paragraph or less? How long did it take you to write the whole thing from conception of the idea to finished product?

JC: It’s a superhero/gangster novel, my own attempt at a Beowulf sorta thing. Like John Gardner’s Grendel, but with more fistfights. Lupo Danish is a strong-arm thug for a real asshole land baron-type, and he’s very brooding and guilt-ridden about it, and then he punches people. I started writing it way back in 2003, and after 100 pages or so, I felt like it was too ambitious a project for a 26-year-old drunkard to do well. So I put it in a drawer and carried on working on other projects, but I always kept Lupo in the back of my head, took notes on it and stuff. Then in 2011, a guy I know was putting together an anthology of “drive-in fiction” and he asked all the contributors to submit novellas which blended two genres of film. So I felt superheroes and gangsters qualified and thawed Lupo out of his cryogenic chamber. I edited what I had from way back, and enjoyed the result so much I expanded it into a novel, which I had more or less done by spring of 2013. Then I pretty quickly got discouraged trying to get it published, until the lovely Australian boys down at Crime Factory figured we might as well publish it. I felt weird bringing it to them in the first place since I’ve been working for Crime Factory since Cameron Ashley made Dave Honeybone’s old print magazine into an on-line ‘zine, and it felt too much like a vanity-press project. But then I figured I did want this son of a bitch out there, and who better to trust it with than my friends?

RM: In what ways are writing a novel and developing ideas for your stand-up act similar; and in what ways are they different?

JC: It’s pretty night-and-day. The only real similarity I guess would be that I try to draw the straightest line between two points. I’ve never been very comfortable with my descriptive prose skills, but I do really like writing dialogue. So I try to convey as much as possible through that. I very much enjoy the novels of George V. Higgins, and he was an undisputed master at dialogue, even if his plots were all pretty much the same. So, yeah, one-liners pretty much go from point A to B with little fuss or muss, pretty much like anything else I write.

RM: If you were a superhero and had the power to change one thing about the industry of comedy, what would it be and why? Do you think that unfortunate tendency will always be a part of stand-up, or is it something that can be corrected if more light is shed on why it’s such a problem?

JC: I dunno, really. I just haven’t had a whole lot of experience with the industry side to say. I think any sort of unfortunate tendencies I’ve run across likely stem from plain ol’ human nature rather than anything inherent in stand-up. People can be assholes, but that’s true pretty much no matter where you are, so you just have to try not to battle with monsters lest you become one. So far, I think I’ve been doing okay with that, though I’m sure it wouldn’t be hard to find a dissenting opinion there. Also, comedy can be difficult going, especially when you’re just starting. There are many sets, many nights, when one will question just what the hell one is doing with the college education one will still be paying off 3 years from now. But that seems to me to be the trade-off. If you get yourself a nice, boring job, you don’t ever have to worry about eating shit in front of a room full of people. But if you’re not cut out for that sorta thing, you roll the dice on a different career path that doesn’t have a 401k or regular hours. It’d be swell if you could quantify the hours and hours of work you put into comedy, be assured that your investment would have some sort of pay-off. But then you’re just back at a regular job. So, I guess it’s all a matter of perspective. Or maybe if you just float a buncha bullshit like the above out there, you’ll begin to believe it and not have night terrors. Either way.

RM: Which part of the comedic writing process do you struggle with the most and why?  Conversely, which aspect of the procedure would you consider to be your specialty; and why would you say that you excel at that particular portion of your craft?

JC: My stock-in-trade thus far has been one-liners. When I started trying to write jokes for stand-up, I played around with observational and anecdotal stuff, but quickly got bored. One-liners are short enough to hold my interest until they’re done. I think that stems from the fiction-writing with which I had originally planned on making my living. I used to write a lot of flash fiction, and even with the novel or other longer-form writing, like I’ve mentioned, I tend to favor the leaner prose, very much hacking Cormac McCarthy or James Ellroy whenever possible. I still struggle with longer form jokes. Every now and again, something will happen to me at the grocery store or the DMV or somewhere, and it feels like the comedy goddess is handing me a bit. So even though it’s not the sort of comedy I’m interested in doing (I still love hearing it; Brian Regan remains a perennial favorite of mine), I would like to continue bashing my head against that particular wall, at least until I can do it. I’d like to have that tool in my kit, even if I don’t use it very often.

RM: What’s up next for you in the remainder of 2015 and beyond? Anything big in the works that we should know about?

JC: Pretty much the usual. I get pretty regular weekend work here at the ACC, which helps supplement my comic-book addiction. I’ve begun applying to festivals, which I’d like to do more of. I did the MidWest Fest contest last month out in Indianapolis, which was a lot of fun. For the last 10 months or so, my partner Jeffrey Berner and I have been running a quasi-monthly show here at the ACC called The Miracle Joke Elixir, which is also very much fun, and Berner and I will likely have more team efforts forthcoming. We used to do a podcast called “If I’m Louder, I’m Right”, which is still available on the exclusive internet, and we’ve recently been knocking around other ideas for a new one. We’ll also hopefully do more two-man stand-up while continuing to grind on our own individually. I certainly wouldn’t mind getting another novel written, or even just a short story or two, but as busy as I am, that doesn’t seem like a distinct possibility in the near-future, but it’s seldom far from my mind either. And just keep on rocking in the free world.

Jimmy on Facebook:  https://www.facebook.com/jimmy.callaway.71

Jimmy on Twitter:  https://twitter.com/jimmytheworm

San Diego Comedy on Facebook:  https://www.facebook.com/ComedySanDiego

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