Seeing everything a little differently: an interview with Caitlin Crombleholme

For Decent Company April: beginnings & endings, Caitlin Crombleholme will be performing a piece about a woman doing her very first standup routine ever. (Spoiler: the routine isn’t going well.) Caitlin and Decent Company producing director Josh Boerman grabbed an early morning coffee and talked about failure, breakups, and coming out stronger on the other side.


JOSH BOERMAN: What was the reason that you wanted to do a play with a microphone, where you are doing intentionally awful standup?

CAITLIN CROMBLEHOLME: Well, when I saw the first showcase for Decent Company, there was something about that space and people just standing up on that stage in the back of a bar that just, you know, screamed “comedy club” to me.

And the idea just sort of popped into my head. It was one of those things where lines just kept running through my brain and I had to whip out my phone and start writing it down, and an arc was developing, and was just constantly narrating in my head about it.

JB: When did that happen? When did that start?

CC: It started maybe, I think, after I emailed you and I was like, “I wanna try it,” and then all of a sudden I had the inspiration. I think just the motivation of actually committing to it jumpstarted a lot.

JB: And do you have any experience with doing any sort of, like, standup or anything like that? Is that anything you’ve ever tried?

CC: No. I’ve never done standup. I’ve never written a play before. I’ve never done a solo piece. There are a lot of firsts. So I don’t know what that says about the fact that the whole conceit is failure in the piece. I guess I was anticipating failure for myself.

JB: Are you— do you fear that? Do you fear failure?

CC: Oh, yeah. Who doesn’t fear failure? Yeah, it’s terrifying.

JB: I feel like for some people, failure means different things, though.

CC: Yes.

JB: And for some people, failure is scarier than it is for other people. Some people just push it away, pick themselves up, dust themselves off. Other people, if they get knocked down, they’re gonna stay down for a long time.

CC: Yeah. I don’t stay down. I get knocked down and then I’m really stubborn about it. Sometimes I make excuses, and then other times I’m like, “No, I need to learn from this.” So I try to be a good loser, but then I try to avoid it at all costs. Which is counterintuitive. Like, everybody says you need to fail in order to grow and know how to do things better. It’s hard for me to accept that sometimes.

JB: Do you want to tell me about an example of a time that you failed, that it sucked and you did learn something from it?

CC: Oh, this is one of those quintessential interview questions.

JB: It is like an interview question.

CC: And I just have one in my back pocket at all times. I’ve so rarely failed that I— (LAUGH) I fail all the time. Lots of fails.

JB: Would you describe them as epic, these fails?

CC: I’m trying to think of a really epic fail. Oh, this was an epic fail. This was when I just got to college and I was trying to be super sophisticated and, like, figuring out what networking was. I was talking to this dean who worked at my college, and I found out that his sister was a higher up dean at the school.

And I was like, “How is it working with your sister? I personally would hate that.” And then I went on this tangent about how I would, like, so bad at working with my sister. And this guy, he was like 30 years older than me, is just staring at me like I am the biggest idiot. And I didn’t realize how badly I failed until maybe like three years later when that experience popped into my head again.

JB: And then when those experiences pop into your head, you visibly, physically— you cringe.

CC: Yes. My blood ran cold and I shivered. And I was like, “I am so stupid.” (LAUGHS) So, like, the very retroactive realization of failure is— those are the worst ones.

JB: What I like about this piece, though, is that you are just throwing yourself into it. And you are aggressively portraying somebody who’s failing, but doing so in a very funny, very believable, very honest way.

CC: Well, thank you. I do think there’s something about that crowd mentality, just being in front of people, where suddenly I feel like you let go of any of the awareness that you have, and you just sort of, like, give into the fact that there is a mob in front of you and you are more open. And take risks that you wouldn’t otherwise have.

It’s kind of like being drunk or something, you know, where the psychosis has broken down, you’re making choices that you never otherwise would, but you do it. And the benefits and consequences are entirely different.

JB: Well, and of course, the character in the play, she is drunk, and she is reeling—

CC: That’s true.

JB: —from a very bad morning. (LAUGHS)

CC: Just throwing all of it together. Yeah. Well, and I think the timing is so key that she hasn’t had the chance to mourn at all yet. She just jumps into it. So, like, so many of the realizations and the epiphanies and heartbreak just happens onstage in front of everybody. Which is the most terrifying, vulnerable thing to do to oneself, but in this case, I saw it as a liberating thing that was necessary for the character, Kiki, to go through.

JB: So that morning that you were mentioning, for the benefit of the people who obviously haven’t seen the show yet, Kiki is dealing with the aftermath of what sounds like a pretty nasty breakup. Did you draw on personal experience from this, or from what you had heard from other people? I’m just curious where that part came from.

CC: There are certainly universal themes and experiences. I have not had that sort of breakup experience. Certainly, I haven’t been blindsided in the way that Kiki is. But people do have that experience of, like, when something ends and you weren’t expecting it or anticipating it. And it’s just like everything around you is shattered. And you have no idea how to process it. Yeah. There are definitely a lot of things that I’ve pulled from my life in this piece, but a lot of it, there are projections onto other things.

JB: Is it like you’ve seen other people who have been in these situations and you’re drawing on that, or?

CC: Yeah. I’ve seen other people, I’ve heard about other people. It’s also just, like, one, everybody’s first play is about a breakup. So, you know, had to satisfy that trope. And it’s also just something people can relate to. I definitely wanted it to be a relatable experience, even if it’s outlandish. Something the content of which people can still sort of connect to.

JB: And I feel like that’s something that’s— I don’t think I did it intentionally, but it feels like this whole month, all of the plays are about breakups in one way or another.

CC: Yeah.

JB: Not necessarily romantic breakups, but they’re about big, fundamental changes, after which nothing can ever be the same again.

CC: Yeah. Well, and it’s interesting that the theme is beginnings and endings when it seems like all the other playwrights have done endings and beginnings. Where, like, when something— it’s that vicious cycle, where something ends in order for something else to begin. We’re really seeing that, like, it’s inverted.

For us to think about any new beginning, we actually have to focus on the ending first. It’s a much darker way to view the world and to create work. But it’s ultimately for the creation of new things and the proliferation of new ideas.

JB: So you’ve said this is your first time doing any sort of solo performance or anything like that. Why this play now?

CC: Well, I just went through the process of applying to graduate school for acting. It was just sort of, like, you know, throw your hat in the ring kind of thing. Like, who the hell knows what’s gonna happen. And I felt very good about the work that I did for it, but after everything, I feel like I didn’t really relish the opportunity to do these monologues and really feel like I’m sharing a part of myself.

Like, there is that veneer of, “This is Caitlin presenting something to you in order to define my future.” So I didn’t feel like I fully gave myself over, or that I really behaved like myself. And so this was a really lovely opportunity to just completely indulge. Just do all the things I wish I could in an audition room in my real life, like, in any context. Which was a lot of fun. And I feel like I don’t often have the chance to just rant and rave for ten, fifteen minutes straight.

JB: But it’s not just ranting and raving, either. It’s focused. It has heart, it has feeling.

CC: Thank you. Yeah, that feeling in the heart, that’s so key. That’s something that I think I frequently can forget about in my day to day life. Just interacting with people. I forget, like, we’re all human, and the reason this community is involved in theatre is because of that connection, because of that heart.

And it’s just so easy to get wrapped up in how vicious and competitive and dark the world is, and lose that little piece of yourself. So, you know, sort of germinating that idea in this piece was really powerful for me.

JB: So how much of Kiki is in you, or vice versa? What do you see that connection as being?

CC: Well, we definitely are— we have a bond, Kiki and I. I imagine that I’m more socially aware than Kiki is. I mean, it says a lot that she went to a comedy night without any friends. I mean, she is there entirely by herself. And then in my head, I would be like, “Ooh. That’s sad.” But in her head, she was like, “I don’t even know what’s going on, I’m just gonna do.” So I feel like that’s a big difference.

But then I think Kiki and I behave very similarly after we’ve had three cocktails. (LAUGHS) You know, which is nice. Yeah. There’s a lot of myself in my portrayal of Kiki, but then a lot of other parts of her that are projections, like I mentioned earlier, of people I know or have heard about.

JB: Because this is a breakup play, we see a character who is very lonely and is searching for somebody else to fill a hole that exists in her life right now. And is searching externally to try to find that rather than looking inside maybe herself a little bit more, which might be a little bit healthier.

And this is a very personal question, so answer it how you will, but for you, where you are now, are you in a relationship? Are you trying to find a relationship? Did any of that inform how you went into writing this?

CC: Yeah. I am not in a relationship, and I am not actively looking for one. I definitely am the type of person where I want relationships and friendships to build organically. So I haven’t, like, overtly sought it out.

But I think moreso than a romantic relationship, something, sort of the guiding idea for me when I was writing this was that Kiki had this whole plan for what her future is. She was going to marry this guy, and they were going to have their wedding, you know, up in Hudson Valley. And then they were going to have three children and then move to Connecticut and have that house.

And, you know, she had it all planned in her head, and that has been shattered, this plan. This preconceived notion that she had that her life would end up exactly how she wanted it to. Which is the case for anybody; nobody’s life ends up like that. And she has this bucket list of all the crazy things she wishes she could do, and she hasn’t done any of them.

And I think bringing that idea into the play was important for me, as a reminder that you do need to take risks. That you should have crazy goals. You should also anticipate nothing ever going the way you plan it.

JB: Right. Because otherwise you end up in a situation where rather than living in an actual real world, you’re basically creating imaginary— you’re ending up in situations where you’re just infatuated with the ideal focus whoever a person is.

CC: Yeah.

JB: Which is sort of what Brian was talking about in his piece that he did in February. It’s like, at that point, is it even a real person anymore?

CC: Exactly: no. She was living in a dream world. Like, her reality was not actual reality, and she’s been thrown back into it so violently, and it does make her— one of the things I really enjoy about the piece is that now that she’s suddenly seen the light, the rose colored classes are gone. She’s actually realizing how unhealthy her relationship was.

And maybe it is a good thing, and she’s suddenly reconsidering everything. That’s one of those realizations that it’s always hard to bring yourself to, but once you go through it, you see everything a little differently.

To buy tickets for Decent Company April: beginnings & endings, click here.

Leave a Comment

Your email address will not be published. Required fields are marked *