Carly Ann Filbin is the butt of her own joke

Chad White

Self-deprecation in comedy is a staple that many try but only a few truly master. Conan O’Brien is a shining example of how to do it right. You get in there, make the joke, maybe go a step further and then move on.

Carly Ann Filbin does just the same thing but takes the extra step to make sure the point gets across. In her web series Single Blond Failure, Filbin makes her character the punchline to the jokes she writes but there’s a method to it. Each episode has one task for Filbin to do and somehow, some way, she manages to mess up someone else’s day because of her actions. I promise it’s a lot funnier than how I put it. Filbin recently told me how the show came together and how things went behind the scenes.

Where did Single Blond Failure come from? I was watching a few episodes and I enjoyed it.

Carly Ann Filbin: First of all, thank you. The origin story is…I’m a comedian and I do a lot of hosting things and I was booking jobs and going in to meet agents. I felt like they wanted me to put forth something that I would consider authentic. For a lot of these things I get hired for, I’m a sex and relationship expert – which is truly not the case at all. I was fine with it for a while but then I met with this hosting agent and she just wanted me to be what I wasn’t. I kind of was like “What am I putting forth that’s kind of contradictory to who I am?”

Around the same time, I went through a breakup. I was kind of obsessed with every girl me ex talked to on social media. Even though I practically knew I was writing the story in my head, I couldn’t help but feel the feelings of jealousy. These girls would post pictures [and I would] think that’s they’re authentic self even though I knew it wasn’t. And I would do the same thing. It’s kind of who I was vs what I was putting out vs who other people were putting out I had the idea of someone who worked at a women’s interest magazine who was assigned articles on love and relationships and had to fake it because she didn’t have any experience.

I was involved in a show called “Awkward Sex and the City” and we would go out of town a lot. On these long trips out of town, I would talk with this comedian whose name is Bobby Hankinson and he loved it. A month later, he called me saying “I’ve been thinking a lot about this idea and, if you don’t mind, I’d like to be involved with it.” I was like “of course!” And he was like “I already wrote the first episode.” He said “magazines are outdated. I think it should be a social media influencer who struggles with herself, her job and her life.” I said “that makes sense.”

And Bobby worked in advertising and he worked with social media influencers for a long time. He’d just recently quit his job. He had so much knowledge into this world. And I have so much knowledge in being hired for things I wasn’t exactly an expert in. That’s what hosting agents would talk to me about all the time; they would use this “work expert.” Bobby and I came together and we wrote the pilot first. Then it was just a web series. Was that confusing or did that make sense?

It made perfect sense! The premise makes sense because the series is described as “a look behind the Instagram filter.” Even though this girl has all the influencer points for being on social media, she still has to fix up her own life.

Filbin: Yeah! This isn’t so much in the web series but [in the] pilot, she’s all about genuinely trying to help people. In order to get people to go to her blog, – she has all these lifehacks and ways to make you life easier – she kind of has to play the social media game. She has a lot more heart in the pilot (but we had to lose that in the web series). She has to play this game and it’s hard but she doesn’t fight it.

Was it a previous decision to make it cartoony in nature? At some point, when I was watching the few episodes, it was pretty interesting the way she acts when she’s talking to other people and when she’s alone. She’s kind of Tina Fey in 30 Rock and Conan [O’Brien] when he’s playing himself on his show.

Filbin: I love that you just said it’s cartoonish. This was a huge writing process for both Bobby and I. He recently quit his job to work on this. We did write the pilot first and we had never written a pilot before. Or even a web series of this caliber. We went back and forth on tone. We would write some episodes that would be cartoonish. Some would be more in the voice of, let’s say, Girls. We just ignored that there were two different voices because we were so attached to the jokes.

One day we realized we were writing more in [a certain] tone; we describe it more as a Kimmy Schmidt. From the beginning, we loved the idea and the character. We wrote so much. It was clear that we, as comedians, this tone was birthed out of our comedic voices. Once we latched onto that 30 Rock tone, we just ran with it. We erased any jokes that didn’t 100% fit with that tone. We love it!

I love that you said Kimmy Schmidt. It is Kimmy Schmidt-esque wherein she’s this very adorable, loveable character but you kind of want to see her mess up just to see what she gets into.

Filbin: Exactly. Bobby and I both love this kind of comedy. I just really love that we got to write a character that does have a lot of heart and does fail often but gets off the ground. She wakes up in the morning with “I have to do this; I have to do social media.” I think we got to write it in a really fun way.

Something else I noticed, humility is very prevalent. You’re able to make fun of yourself [easily]. When you’re pulling out the shirt in the first episode, and you were trying to hide that it had a stain, you pulled out an iron from a purse and a Taylor Swift coloring book. That’s amazing!

Filbin: I, personally, am big on a lot of visual jokes. I’m an improvisor so my philosophy is show, don’t tell. The idea is humility across the board. Bobby and myself, as comedians, we’re totally comfortable with making fun of ourselves. We’re aware of our flaws. I think it’s fun to see a confident female character make fun of herself but not hate herself. It gave so much allowance for a ton of jokes.

One of my favorite things about the entire show is that they’re simple in nature and self-contained. “Pizza,” for example, is about getting pizza and the issues of getting pizza. You don’t stretch out a three-minute story into thirteen minutes.

Filbin: We worked really hard on that. It was difficult because…I guess in some ways writing the pilot first had a lot of pros and cons. The pros being that we knew this world, this character and that we knew how to tell a story. The cons were we now had to tell the story in three to seven minutes instead of twenty two minutes. We worked really very hard. We did a ton of rewrites.

Our director, Kate Riley, really acted as a writing coach as well. It’s funny you brought up “Pizza” because we wrote it and the description was a paragraph: “A girl who wants pizza tricks a guy into thinking he’s going home with her in order to get the pizza.” There’s not a lot of dialogue. We almost focus grouped it when we had a very rough edit of that episode. A lot of people didn’t understand it; it didn’t transfer from the paper to the small screen. That was the one we edited the most. We had to change all the voiceovers. We did a lot to that episode just to make the point very simple and clear.

Follow Carly Ann Filbin on Twitter, like her on Instagram, and check out Single Blond Failure on YouTube.