Staying Motivated and Staying True with Christi Chiello

The first time I saw Christi Chiello perform was three years ago in the basement of a bar at comedian Jared Wilder’s show Laugh and a Draft. It’s hard not to notice Christi Chiello when she’s on stage; her voice is unexpected, as she observes in her act, and when spoken into a microphone it demands attention. The quality of her jokes and the way they fit into her very upbeat and optimistic personality make her hard to forget.

Chiello recently appeared on Comedy Central’s Roast Battle at Just For Laughs Montreal, where she roasted the previous year’s champion Jimmy Carr. She is probably not the first comedian to come to mind when you think of great roasters, but her personality and the originality of her premises pair fantastically. Although Chiello did not beat Jimmy Carr, the tension and drama of their roast was certainly a high point in night one. We watched her waver between bold self-confidence and open nervousness while Jimmy Carr laughed his strangely unsettling laugh in the background. As Jeff Ross noted, the two were very well matched owing to the compatibility of their writing styles, and to great effect.

I recently sat down with Chiello to chat about how the roast came to be, whether her nervousness was all true or just for show, and what keeps her motivated.

Given your very upbeat personality and your distinctive voice, watching you do roasts is really a unique experience. What is it that drew you to roasts in particular?

I think I discovered pretty early on that, for better or worse, there’s definitely shock value in me and my persona saying things that are dirty or raunchy or swear words or whatever. When I first started comedy, that was all I did. I knew if there was this seemingly cute girl who said “pussy,” that I would get a laugh. I think I relied on that a lot early on, and it lead to some interesting discoveries, but I wasn’t really doing the kind of comedy I wanted to do.

I’ve always loved roasts, I’m a big fan of the Comedy Central roasts… I think there are a lot of reasons why I started, but I think I like the challenge of it. Mike Lawrence is a big influence of mine, and he’s kind of a mentor to me. He talked to me about it and sort of suggested I do it, and I did my first one at The Stand.

I feel like roasts come from just sort of the way comics tend to interact with each other. There’s a lot of loving teasing between comics, although I don’t think that always comes through in roast battles.

Yeah, sometimes it’s just cruel. There are definitely some comics that just wouldn’t want to do it, because they do feel it’s so negative. It’s interesting, because I do feel like, as a person I’m very positive, and I’m very happy. Although, I’ve started to get more self-deprecating in my comedy this past year, which is something I never used to do, and I never really liked. I think just comes from… I remember when I first started comedy, comics would say things to me like, “Oh, you’re so happy. Just wait until you’re eight years in. You won’t be happy anymore.” I remember being like, “Oh God!” in a miserable way, like, “Oh, that sucks.” Not to say they’re right, but as you keep doing it, when you get more and more rejections. It just becomes like…

You just start getting used to the whole routine?

The routine of it, and just a knowledge and understanding of what a grind this is, and how much time it takes, and all of that stuff lends itself very well to feeling a little defeated sometimes, and just trying to find the humor in that.

Oh definitely. There’s a way to do self-deprecating material where it doesn’t look like you’re just being a sadsack, it’s practically like you’re roasting yourself out of appreciation for who you are.


When did you find out you would be roasting Jimmy Carr, by the way? Did they just spring that on you, or did you have like a week to prepare?

Well, I got asked to do a show called Road to Roast Battle. That was when Jeff Ross and the host Brian Moses and this group called The Wave went on a cross-country tour to four cities and chose ten comics in each city to represent the city. New York had a battle at the Gramercy Theater. We all knew that Roast Battle show was going to exist and was going to take place in Montreal.

For Road to Roast Battle I battled Sam Morril, who’s a phenomenal joke writer. I remember feeling like, “oh Jesus.” I was thrilled to have been asked and just to be… everyone who did that show really did feel very “next level.” I was just thrilled to be there. I didn’t win my battle against Sam. I was really happy with how I did, but I didn’t win. I didn’t really expect to win. I didn’t think that Montreal was an option, but for whatever reason they liked me on that show. I guess they thought I was different, so they asked me to come to Montreal. I found out two weeks before. I was babysitting.

So you had two weeks to prepare roast jokes for Jimmy Carr?

No, they told me that a few days later. I had over a week, though. At first it was like, “We’re still deciding who else is going. We’ll be in touch.” That became like, “Oh, all right. I heard Mike Lawrence was going,” so we’d kind of talk, and “Oh, I hear this person’s going; Sam is going.” We were trying to put together the pieces, but before that even happened, I got an email telling me that it would be Jimmy Carr.

Oh God. And what were your immediate reactions to that?

My immediate reaction, truly, was, “I think I know who that is, but I’m not 100% sure.” Because I knew that I knew the name, but I am admittedly really bad at placing people. Then I remembered that I’d seen that he did a Netflix special, and it came up on my suggested Netflix special. It took me Googling him to be like, “Oh my God! He’s that British guy. Holy shit.”

Instinctually I was like, “Is this a prank?” I think it’s very fair to say that I’m the biggest underdog that went, the biggest no-name comedian with no credits. Like, I have credits, but this was a big deal for someone like me. Jimmy Carr was the one to beat. Last year they did a roast battle in Montreal, and it was so successful that they made it into a TV show this year, and Jimmy Carr won the whole thing. He’s the reigning champion.

Oh, man. That just makes it so much more stressful.

It’s so nice to talk about this! I told my mom, “It’s the silly tall person.” I remember I did feel immediately very scared, but then I felt proud of that, too. I thought, “Okay, this is going to be great exposure and a great opportunity.” Not only that, and this might be bad to say, but going there with so many people who I look up to and who have done really great things in their career, it kind of made me feel like I have a lot less to lose. Like, imagine if Jimmy Carr or someone lost… I’m still doing open mics. I felt like, “Wow, I’ve already won just by being here,” because all I can do at this point, it sounds so cheesy, but I got there by just being myself. I wasn’t about to think, “What’s my plan? Be the person that they liked, be who I am.” That sounds so cheesy, but I never knew that until recently that you really can just be yourself.

Right, because clearly they already liked you. With that in mind, what was it like right before you went out?

I was surprisingly fine. I think, to be honest, I was almost more stressed out before my roast against Sam at the Gramercy, because that had been my biggest show to date. It was the biggest place I ever played, the biggest audience. Dave Attell was a judge, and I was fangirling over him. That show really helped prepare me. I think had I not done that show, I would have been more scared. I had just come off of doing what, to me, was a big show. I was happy with how I did it. That helped.

It’s weird, because I just kept telling myself to really feel like I deserved to be there, just like everybody else did. That’s a really hard thing to learn, because it’s a fine line. I want to be like, “Oh my God, thank you. This is the greatest opportunity in my life!” and cry and be like, “Thank you so much!” Then another thing is like, “Christi, act like you deserve to be here.” Act like you did the work and, yeah, I could do it because I was prepared to do it, and to know that.

Yeah. There’s also like a sort of confidence in being honest about being nervous. It’s kind of the same as what we were saying earlier about self-deprecating material; it comes from a place of confidence and acceptance.

I’m happy to hear it comes across that way, because I would agree. I think to a certain degree it just humanizes you a little bit. Like anything, in excess it’s a little too much, but when people can share in, “Oh, this shitty happened to me,” and, “Oh my God, that happened to me, too,” it’s universal. Sometimes, sadly, I think that I am funniest when I’m sad. I went through a bad breakup, and I felt like I was killing it that week, because you have this feeling of, “I have nothing else to lose. My life is over,” and it’s the dramatics and the way you heighten that, it makes for some fun comedy, because you truly don’t care. I think so much of us in comedy really try to learn to not care. That’s a hard thing to do. I think when you really feel like, “Oh God, I just don’t care,” if something really bad happens, it puts things in perspective; it helps.

Also it’s really hard to learn this in the moment, but it’s like learning that the bombs are probably more important than the nights you kill. You learn from a bomb. Just yesterday I had kind of what I thought was a bomb. I did a podcast, and it felt like I wasn’t really being myself. I felt like I wasn’t really… It was a lot of people there, and I struggled to sort of have a voice. I didn’t want to climb on people, and I didn’t really feel like myself, basically. I’m very hard on myself. I’d beat myself up a little bit. “Christi, why didn’t I chime in more? Why didn’t I make more of an effort to still keep my voice, to speak up and all these things?” Ultimately I learned so much from having had that experience, so next time I’ll know.

As much as it sucks when you’re doing it, it will happen to us forever, and it’s how we learn. I’m really trying to teach myself I can’t expect to know how I’m going to feel all the time. That’s why I think this past year has been so great, because I’m finally learning… This is so cheesy. Cheese alert! I’m finally learning who I am as a person. I think that’s making it easier to be a comic, because I think I’m just being comfortable in my skin and learning what I like. Before when I was 24, 25, I didn’t know who I was, let alone what kind of comic I wanted to be. I had no fucking idea, and I still feel like I don’t know. I know I can feel that I’m getting there.

Do you feel like, if you’re ever on a run of just bad nights or whatever, is it more effective for you to lean in and do more spots, or is it better to take time out for a little bit and then come back?

That’s a great question. Honestly, I don’t know. If there were to be a new comic who would ask me just that question or what would you suggest, I think I would just say it’s totally circumstantial. Might sound like a cop-out, but your story is so different from my story. It’s so different from whoever’s story. You just have to do what feels right for you. Some people, there are people that do four open mics a night and kill themselves, and are out just working their day jobs. They’re exhausted and they’re unhappy. There’s a huge a part of me that can really admire that, but there’s another part of me that if that works for them, great, but do I think that’s something everyone should have to do? No. I think it just depends. I think you’re the only one that knows the reasons behind what you’re doing and what you’re struggling with.

Somebody who’s naturally just nervous to be in front of people, let’s just say, or maybe they have stage fright or whatever, yes, I think I would encourage you to be on stage as much as possible. If that’s something that’s never really an issue for you, and it’s the writing, if you want to take a couple of days and really look at your notebook, that could be just as beneficial as doing a mic for four people who are going to be in their notebooks anyways. It’s totally circumstantial. I just think you have to do what feels right for you. It’s okay to not know that.

I feel like everybody can kind of identify with feeling spent, right? Like you’ve been pouring so much energy into something and just need to detach. I think what’s more interesting for a lot of comics is that sometimes comedy is both the thing that drains you and also the things that fills you back up.

It’s so profound.

Right? So smart. That’s the underlining message of all my interviews.

It should be the title of this interview.

“Phil Is Very Smart, and Christi Chiello Was There, Too.” But I do think that’s related to what you’re saying; like how you keep yourself going in standup depends on how you feel that you’re exhausting yourself. There’s no one right thing to do for every comic.

Yes. Although I do think it’s always great to have… I work really well with deadlines. That’s kind of going off topic, but I do think that, for example, if you had a really bad bomb, I would never think of cancelling your next spot. It’s part of the healing process, to just get back out there and do it. I definitely think that that’s an important thing: just to keep with the repetition and to not let the bombs prevent you from trying it again.

Do you think that being in tune with what you need personally is a result of just maturing, or is it a result of maturing specifically in standup comedy?

Both. I do think it’s both. I think I feel a lot more than the average person. I’ve always been very into feelings. I’m always really analytical and very in my head. I’m very into communicating. It’s exhausting to be around me. That is something that could very much be uniquely Christi. A lot of people do it too, but I think I do it in excess. I think sometimes it’s just better to not be in your head. But, I think with comedy… I think even technically speaking when you’re looking at words on the paper, you’re going through a joke that’s two sentences long, and you’re trying to fine tune it, so yeah, you’re being analytical. Jesus, I wrote gross jokes for this show that I would spend an hour on a two-sentence joke, being like, “Oh, should I say ‘the’ or this word?” It’s stuff that feels arbitrary, but it’s not; it’s little nuances, and it can be so technical. I guess it’s good that I’m analytical sometimes, but I do think comedy can kind of force you to look at the work you’re doing and look inside yourself, because it’s like art. You want to be your truest self, but also be good, hopefully, and know what that is.

Right. It’s hard to kind of untangle them. In a way, you development in the career is also your development as a person, so it’s linked.

Yeah, I guess so, which is so weird. It’s weird to think, but I think it’s exciting, the whole uncertainty of things has truly never scared me in a way I think it scares other people, with not feeling stable and not feeling like you have security, and not knowing. But I take a lot of comfort in that. I like thinking that what I’ll end up doing might be a thing that doesn’t exist yet. I think that’s great. That, to me, is possibility. It doesn’t frighten me. I really do have a ton of faith in myself and my abilities, and optimism. That has a lot to do with just my character, too. Standup aside, I’ve always kind of been that way, just faithful and hopeful, and not terrified.

I do believe fully that I’m exactly where I should be, and that you’re exactly where you should be. I really live by that, being like, “Wow, I’m where I need to be, and I need to learn these lessons. Whatever I’ll end up doing is what I’m supposed to do.” I know it sounds very idealistic, and maybe it is, but I’d rather have that than not.

Is this comfort something that’s sort of come from the experience of having to get used to that repetitive grind of comedy? Have you always been this comfortable with your position in comedy?

No, I wouldn’t say that, because I don’t think I am. It’s hard, because you don’t want to be satisfied, because you’re always wanting more. You don’t want to be complacent. That’s always a driving force, but it doesn’t feel unattainable. It doesn’t feel so far from my reach, I guess, now as much as it did before. It’s interesting that I did the roast battle, because I do feel like I’ve always kind of felt in a sense like an underdog in comedy. I think a lot of it’s because… Not to victimize myself. I’m sure a lot of people feel the same, especially when they first start. But I like when people underestimate me. I like when no ones pays me attention. From the get-go until now, because I really do feel like, “Okay, if you don’t think I can do it, just watch me.” I think that works for me in a sense that maybe it wouldn’t work for other people.

Totally. Like, in your own head you’re content with what you’re producing. A part of what keeps you driven and keeps you not totally satisfied is the understanding that there’s so much more of that to show to people. Toward the end of your roast battle with Jimmy Carr, there was a moment where you were taking a breath and looked like you were rehearsing the joke to yourself. Was that real, or was that for effect?

That was a hundred percent real and in the moment. I did not plan on doing that at all. I remember thinking in the past when I do roasts, I love to jokingly talk shit like, “You’re going down!” That’s like a part of the sport behind it. I really enjoy doing that. I’ve also been fortunate in that I’ve only roasted people I’m pretty good friends with. We would really have fun making videos for each other, but with Jimmy it felt very different, because I really asked myself, “How do I feel about this?” I think I can’t go in there and say “You’re going down!” What? I feel like that would be playing a role that wasn’t me.

I walked out knowing my jokes and feeling good about them and feeling like myself. I remember when they asked, “How are you feeling?” in that moment just being like, “I’m feeling really scared.” I remember I felt good. I felt a release in saying that in a way that I didn’t expect. I think that kind of helped me in the battle.

Jimmy, he was just great. I don’t think I would have expected anyone to be as kind as he was. I think what matters, I think both people at the end of the day, you just want a good battle. No one wants to just destroy the other person. It’s a dance; it’s a tango. People want to see a good battle, because if we don’t, it’s awkward. You feel weird and bad, and “Oh, God, that person is going to go home and cry.” Jimmy was like, “Let’s have fun,” he really was so supportive.

What did it feel like when the judges were evaluating your jokes? Kevin Hart seemed to be particularly enjoying himself.

I almost cried when he was talking to me, and I remember being like, “Don’t cry. Don’t cry. It’s so embarrassing,” but I was just so happy. It was truly the happiest moment of my life. I remember thinking, “Oh God, I hope I didn’t look amateur. Was it a mistake [to say I was scared]?” I did have good jokes! Were my jokes maybe overlooked because I was so nervous and so giggly? I did think about that after, but then at the end of the day, I really do feel like I was really proud, if not for anything else, because I was myself. If I’m going to lose, at least I could say I did me.

Photo by Mindy Tucker.

Christi Chiello co-hosts a weekly show, “White Chocolate Sundaes,” alongside comedian Petey DeAbreu every Sunday at The Standing Room in Long Island City, as well as a monthly show, “CATS, A Comedy Show” with comedian Molly Austin the first Monday of every month at Leftfield in Manhattan.

Phil Stamato lives and writes in New York, where he may also be seen standing up and telling jokes. If you’ve read this far you are legally required to follow him on Twitter.

Staying Motivated and Staying True with Christi Chiello