The Kaplan-Ruby Letters, Part Two

The second (and final) part of an email exchange between Myq Kaplan and myself. (Check out Part One.)


Interesting that you feel your writing outpaced your performance skills. I feel like there's a certain confidence you get from performance reps that is hard to fake. It's like audiences can tell if you've been in the trenches before and for how long via some invisible transmission.

Sometimes that's the way I feel about shitty gigs — each one is another...well, let me backtrack. I feel like every standup needs a suit of armor. And the audience can tell whether or not you've got this suit. But the only way you build this suit of armor is one little piece at a time. Each shitty show or dingy mic is adding one more tiny piece of armor to that suit. So it takes years to get a full suit together.

Or at least that's what I tell myself so I feel better after shitty shows and dingy mics. After all that crap you begin to think, "There's nothing you people can do to me that hasn't already been done." And I think people sense that and respond positively to it.

As for your questions about my early days, I think I was probably more confident than I should have been when I started. For one thing, I had been performing music live for years so I think that helped me with feeling comfortable onstage. And early on, I lucked into some good gigs and got semi-regular spots at a club for a bit. So that prob made me think I had more juice than I really did. I think that lasted for six months to a year and then I started doing more rooms and things shifted and I started reevaluating everything. Around that time, I started taking more chances and trying different things (characters, one-liners, changing how I delivered jokes, doing weird videos, etc.) in order to figure out what felt most right for me. That involved more failure but I think I learned a lot from it. I also started to figure out who I wanted to be onstage more. That helped me filter out what I did and didn't want to talk about.

Oh, and We're All Friends Here started three years ago and that had an impact on me too. It's the most fun I have performing and it's all about being real and tension/release. Sometimes we get laughs at that show that just feel deeper and more human than the ones you get from doing jokey jokes. It's made me want to bring that same vibe to my standup. Also, I'm amazed when a standup is offstage and being really interesting talking about their own life and then they go onstage and talk about silly pop culture shit. I don't want to be like that.

(But then again, I have a newish quick joke about the Black Eyed Peas that I tossed off but it does well...so do I really give that up? It's a wrestling match inside my brain. Now I'm trying to figure out why I care about the Black Eyed Peas and trying to see if there's a way to frame the joke so it's about me and my worldview instead of just "those guys are dumb.")

And yes, I do like confident performers. Doesn't everyone? Maybe the ideal is someone who is confident yet also taking chances at the same time. So there's a hint of "this may not go well" involved too. Danger is exciting. (Also, criminals are sexy.)

Back to you: Is there a system to how you prioritize material? What do you know now that you didn't know years ago? Do you just trust your gut or do you have a way of knowing what's worth working on? I could see you with a spreadsheet of topics/jokes. But maybe that is because I feel like comedy, in some ways, is a series of math problems to you.

Also, you're performing for much bigger crowds now post-LCS, right? How has the size of the audience changed the way you perform? Is it a letdown when you come to a struggling NYC show and the audience members are apathetic?


First, is your Black-Eyed Peas joke that you want to give them black eyes and pee on them? Because if it's not, then it's mine now. Whether I want it or not. But if it is yours, then I like it.

Regarding comedy being mathematical to me, I'd say there's some truth to that. I'm a mathematical person, though I'd say that a lot of us are, maybe not as explicitly, but most of us will do a cost-benefit analysis at some point of "I like this joke but the audience doesn't, so how much time and energy and work do I put into shifting those scales before I decide to cut my losses?" Ideally, the equation is "I like it + the audience likes it = everyone wins," and I would say that my prioritization is based on a shifting equilibrium of the components of that equation. (I would say that if it made sense, that is.)

I'm not sure exactly why or explicitly how I'm better at prioritizing now. Probably it's some combination of knowing what I like about myself and my comedy now more than in the past (when I'd be more beholden to what the AUDIENCE liked), along with just having lots more opportunity for stagetime to stick with the things that I like and push them into being what I want them to be. So maybe it's not prioritizing at all. Maybe if I prioritized differently, I'd still net positive results.

One thing that I do now that I didn't do as much in the past is riff a lot more when I'm working on new material. Two big inspirations in that vein are Rory Scovel and Micah Sherman. Seeing Rory leave his material and just follow any tangent to its logical (or illogical) conclusion is wonderful. Same with Micah, just always willing and able to just keep creating based on whatever twists and turns are happening right there in the then and now (where now is also then). A lot of punchlines of mine ended up being the result of just continuing to speak after I thought the original joke that I had conceived was over. What Paul F. Tompkins does is also a major inspiration, with his show-starting riffing.

And that actually goes along with why I love doing shows like Hot Soup, or Chelsea and Aalap's show that I just did last Friday. I sometimes have MORE fun with a small audience than with a gigantic one, depending on the circumstances. I just did a weekend headlining a club in South Carolina, and while Friday and Saturday had packed houses, my favorite show was Wednesday, which almost got canceled but at the last minute about 20 people ended up being there, and it was the most fun. Sometimes a packed Saturday night crowd brings with it the feeling of obligation to "play the hits" or "put on a good show," as opposed to what I did with the smaller crowd, which was just being more present, more in the moment. And that's not to say I don't try to do that with bigger crowds also; when crowds are good, I'll go off book as much as possible, forging new joke paths and birthing new joke babies. But when there are fewer people, sometimes the capacity to do that is optimized in a way that isn't quite when the room is full. Or maybe it's a constraint I put on myself.

Here's a question: you're a person who I believe enjoys comedians who are in the moment, AND comedians who are revealing deeper truths about themselves. Does one hold more sway over your comedy heart than the other, if they're at odds? By which I mean, someone can perfect a routine about their most recent heartbreak, someone could do a hilarious and poignant one-person show about a wrenching issue. But someone else can be in the moment and just be creating hilarious nonsense. Obviously some folks are capable of both. Rory says real things in his standup, but also some of my favorite moments of his are just spontaneity that doesn't necessarily have a higher point other than being hilarious. For you, is there a way to say that one moment is more meaningful than another?

The way I write my comedy now, in its ideal form, is shifting back and forth between having a spontaneous moment on stage, and then analyzing and mining that moment later for future use, which will lead to future spontaneous moments, which can then be capitalized on in the future-future. Etc.

I think that sheds a little light (to me) on the way I prioritize as well. Every time I listen back to a set where something new (and in that moment, real) happened, I am excited about getting onstage again to share that moment with the next crowd, to see what will come of it then. And if it's happening with different jokes, new tags arising, new lines of thought that I want to follow, it's like a series of intertwining streams of consciousness that are choosing to be told rather than my doing the choosing (or I am choosing it, but simply for the reason that I'm interested in covering as much new ground as possible, mapping out a wider and wider area for my comedy to cover). I don't mean to get too new agey and decree that I'm some kind of vessel or anything.

I just love coming up with new things and perfecting them as much as possible, and seeing where that perfecting leads, to other new things. Perfect makes practice.

With regard to the idea of taking something positive out of every lousy gig, I fully support that, and have experienced it, and still do. I go into every show situation optimistic, and aim to come out that way as well. Hopefully at least one new thing happens in each show. You're a step ahead of where you were. One new horrible audience didn't destroy you. You're ready for the next horrible audience. Or readier to make them a good one.

The right combination of caring and not caring is key, I think. Do everything you can, but know that not everything is within your control, and that makes more things BE within your control. Know that we all die eventually, so why not be fearless when we're alive. The only thing there is to fear is death and pain. And those will happen anyway, so why add fear to the mix?


Re: in the moment vs. deeper truths. The easy way out is to say a hybrid of the two is ideal. Maybe an 80/20 ratio of prepared/riffed material? (Look, we brought math into it. Pareto!)

But if I had to choose, I'd go for the prepared, deeper, truthful material. This is why I prefer standup to improv. It lets you have a point of view. You can actually make points and say something. I think it can lead to real philosophical insight and deep truths. That's pretty rare in improv.

Don't get me wrong, improv/riffing can be magical. It's often the stuff that makes me laugh hardest. But it also tends to "evaporate" practically instantly. You can never tell someone about a great improv show you saw. Well, you can but it's kinda like telling someone about one of your dreams. They are items #1 and #2 on the "you had to be there" list of things. Great standup lingers more.

I do think riffing is a good way to develop material though. In my experience, it comes out sounding a lot more organic than written material. Related: One of my favorite things onstage is when something gets a laugh and I have no idea why it got a laugh. I feel like that's the audience teaching me that something is funny.

PFT's opening riffing is interesting. I've seen him live several times and it seems like it's a challenge to himself to see how long he can go riffing. As if that's the most fun part of the show for him. The way I often feel about riffing — unless you're a master at it like Rory or Jimmy Pardo — is that it's a bit selfish (i.e. more pleasing to the performer) while the prepared material is generous (i.e. more pleasing to the audience). Or, said more simply: riffing is for you, prepared material is for them.

Also, you bring up a good point about the freedom you get from doing less than perfect shows. Paid gigs/big crowds come with a different set of expectations. You've got to deliver the goods instead of just doing whatever you want. I like that pressure but I can see how you'd also long for a low stakes environment after a while of "ideal" shows.

Phew, well exchanged. Any final thoughts?


Final thoughts! Boy, do I have them! Get ready!

First, let me say I'm a huge fan of deep truths and philosophical insights. Furthermore, let me say, what if the deepest, truest, most insightful philosophy leads one to being in the moment? I'm no zen master, but I am a zen dabbler. And I'm not just trying to do semantic tricks here; sincerely, wisdom of the ages has often lauded the moment, the now. Not to say that the future doesn't exist (but does it?), or that we shouldn't consider it (but should we? yes, probably)...

This is actually something that I consider whenever I eat psilocybin mushrooms. As a person concerned with having the richest, fullest experience in life, I find myself (present) at odds with myself (future). Should I just experience the amazing time I'm having right now? Or should I attempt to remember or record important parts of that experience for later? Sometimes it seems like just laughing in the present is the way to go, and sometimes it seems like important truths are reached, sometimes during those laughings, and they should be retained...

And that's only considering myself, and not an audience. The idea that riffing is for the comedian and doing prepared material is for the audience makes sense, in a way, but also misses something. Some people love seeing material created before their eyes and ears (next to their ears?), even if it's in the rawest form, some ESPECIALLY in its rawest form. I definitely have had times when a riff leads me somewhere that I and the audience know might be more polished in the future, but is more real in the present. And it's not just fleeting things. I saw Stanhope one time at Comix do a show where he spoke to a real-life therapist, as part of a concept show where the therapist would just chat with the comedian about his actual potential problems. Stanhope was just being himself, in the moment, and also saying very real things that were lasting and insightful, made MORE powerful by the fact that they were in the moment.

Though that is going back to the copout you addressed initially, that obviously if both are possible, that could be the best. And it's an additional copout to use Stanhope as a reference, because I think he's one of the best thinkers and funniest comedians, and not many people do what he does as well as he does.

But that said, riffing isn't ONLY for the comedian, when I do it, at least. Number one, I'll only really get into it when I feel like the audience is there with me for it, and them being into it is part of what makes me able to keep going with it. And yes, sometimes I might reach a point where, if it were prepared material, I might have stopped a moment sooner. And perhaps if I re-create that with another audience in the future, I will indeed stop before I reach that point. But that means that riffing wasn't just for me in another way; it was also for that future audience. Riffing in the present serves the future crowds for whom it will no longer be riffing. Comedy as time travel.

That said, of course I don't have all the answers. And maybe the monks who just sit all day being in the moment don't either. But there is something very real and truthful about a moment, even if it cannot be explained without "you had to be there"-ing. But maybe that is the ultimate truth. The monk doesn't say "you had to be there." He says "be there." Or maybe he doesn't say anything. Or maybe he's a woman. A bald lady monk. My point is, become a monk, do some mushrooms, and start riffing. Somewhere in there, you'll find the truth you're looking for.

1 comment:

Abbi Crutchfield said...

This was a nice read. I don't see how anyone can say that everyone dies, because it hasn't been proven yet. It's probable, but it's not a certainty in my book. My book is called, "I Can't Comprehend Eternity or Infinity". Speaking of math, you guys are both musicians which probably explains why you see math in your approach to comedy. Or you grew up watching Square One, the comedy sketch show about math.

I have a theory you can save for the "Ruby - someone else Letters": any goal is achievable by any comic, but each comic gets in his or her own way of achieving them. Whether that's intentional - like sacrifices made for family or money, or unintentional - like succumbing to self-doubt or laziness.

Moving on/Subscribe to my newsletter

I only post on rare occasions here now. Subscribe to my Rubesletter  (it's at  mattruby.substack.com ) to get jokes, videos, essays, etc...