Jack in a Box is New York City-set sitcom. It won a 2013 Writers Guild of America Award for Outstanding Achievement in Writing Original New Media and was nominated in the same category in 2012. Jack in a Box also won Best Web Series at the 2010 New York Television Festival. It has been featured by numerous media outlets, including The New York Times, Tubefilter and NewTeeVee. This essay is part of Televisual‘s “Indie TV Innovation” series.
I never intended to create a web series. I definitely never intended to create one that ran over three years, had 4 seasons and 31 episodes. Nope. That was not part of my plan. I certainly didn’t intend to create a web series that would go on to win any sort of award. What I did intend was to write/produce/be in one video for the web. Take a baby step, a small risk. That is the smartest baby step I ever took.
Jack in a Box, happened by accident. It was 2009. I was bored. I was bored out of my effing mind. And frustrated. And maybe a lil’ angry. When you are a character actor in college, teachers always talk about paying your dues and say “You won’t really work until you are in your 30’s” and while this is not always (but often) true, they forget to add, “No really. I am for realzies, kiddo. It might suck for a long ass time and you are going to have to have a crummy day job way longer than you ever imagined and you might gain weight because you spend all the money you make at that crummy day job on cigarettes and tacos and OH Lord are you gonna feel like you’re going nowhere superfast and want to give up…unless you make your own opportunities. Make your own opportunities and things might not be so bad.” Personally, I’d suggest adding all that, or a version of all that to any Performing Arts professor’s spiel given to the weirdos and “characters.” Substitute whatever you like for the cigarettes and tacos, but get the point across. Sitting around and waiting for something to happen is the quickest way to get very frustrated and go slowly insane.
I was fresh off of a 2 ½ year gig at VH1 doing the Best Night Ever video podcasts on Sunday evenings for their Best Week Ever Blog. Once a week, I’d watch a bunch of TV, write jokes about it, sit in a tiny room in front of some colored paper and tape myself telling these jokes and setting up clips. The next day it would be on the internet. That was amazing to me. Before that gig, I had only done theatre, a little bit of stand up and some storytelling. I had zero experience with film and television. Theatre is my first love, but I was amazed at the sheer reach of little video on the web. Now, these weren’t masterpieces; not by any stretch of the imagination. I can’t even be sure that they were viral “sensations”, but one thing was for sure: a single video would get substantially more views than a four week run of my solo show in an un-air-conditioned theater in the basement of a book shop. It was addictive. At the time, making jokes about the vocal qualities of contestants on “Big Brother” and setting up clips from Rock of Love (oh, how I miss Bret Michael’s dirty harem) once a week gave me a sense of purpose and a creative outlet I needed while working my day job.
That gig ended and I spent most of 2008 trying to figure out what to do. (By “figure out what to do” I mean I “sat on my couch and stared at the walls letting myself be perpetually melancholy.”) Eventually, I met a documentary filmmaker named Marcie Hume. She had a nice camera and great sense of humor and knew how to use both. I had been tentatively writing down ideas based on my day job, working at an off-Broadway ticketing agency. Was it a play? Was it a film? Was it a journal never meant to see the light of day? I didn’t know. Then, one day, I asked Marcie if she would shoot a teaser for an idea I kind-of-sort-of had. Just a small web video about a guy named Jack who worked in a box office. It would be a montage of his phone calls throughout the day. I thought this would be a good way to test the web video waters on my own terms and figured I’d keep it real simple: just me, one camera, a script. I am also secretly lazy and thought this would be a trailer for something I’d eventually do many months down the line. Then I saw a rough cut of this kind-of-sort-of-idea we shot. I started to sweat and thought: Oh no! This isn’t a teaser. This isn’t a one off. This is a first episode. Sh*t. A first episode of what? What am I even doing? Panic set in. Good panic, I guess? The line between inspiration and panic is so thin for me. In hindsight, let’s just call it “Inspiration!” It sounds much better that way.
So, I found myself suddenly aware that I wasn’t making a teaser video, but beginning a series. I quickly had to wrap my mind around what that meant and what my plan was. If I was going to do this, and it looked like I was, I wanted to have a clear vision from the get go. I started simple. I knew I wanted to have cupcakes. That was easy. What else? What else? I decided I wanted Jack to be a flawed antihero of sorts, who was prickly but always inherently likable in spite of his short comings. Most importantly, I wanted to focus on his vulnerability and embrace his sadness from the get go, then find the humor from there. It was important to me that the humor come from a very real place, but I also wanted to leave room for absurdity. For example, all the other characters would have the volume/energy turned up about 10-15% more than Jack. Jack would be the straight man in this world, and we would be seeing everyone and everything through his squinty little eyes. I knew that setting the story in the theatre world had the potential of limiting my audience. So once I knew this was a series, I made it my goal to stay true to the very specific situation of the story I wanted to tell (a struggling frustrated actor spending his days working in a theatre box office) but also attempt to make it something more universal, exploring the themes of feeling lost, stuck, the desire for more, the feeling of being wildly frustrated by the human race, but also desperately wanting small connections. I wanted to attempt to make a series that would not only speak to my theatre pals and customer service heroes, but a larger audience.
Whew. That wasn’t so hard. That seemed like a good place to start. I released the first episode, wrote some more, shot two with Marcie and then she moved to London. Oh no. I was just getting into a groove here, and was getting good at turning that panic into inspiration. She was so great to work with, how am I going to keep going? This could have been the end of it all, but there was a voice in my head saying, “I like the web. It’s addictive. I am enjoying this little experiment. I want to keep taking the risk.” I approached my friend Jim Turner and asked him if he would shoot some episodes. “Just a few,” I said. I didn’t know how long I’d keep doing this, but I knew I wasn’t quite ready to stop. Luckily, he said yes and was not only easy to work with but also fun, passionate, committed and patient. Ever so patient. Jim took the shooting style Marcie helped establish and ran with it immediately, making it his own. Eventually he wasn’t just shooting and editing, but also co-directing with me, always keeping an eye on my acting when I was in a scene and being a very calming presence at all times. “Just a few” episodes turned into 28 out of the 31. When I tell people that it was a teeny tiny operation, I’m not joking. It was just me & Jim, a couple of lights, the other actors and some croissants I’d bring from Astoria. Teeny tiny was fine by me. Jim & I really enjoyed working with each other, so we just kept going.
It’s hard to pinpoint exactly what made it all work, why I kept doing the series for so long. Previously, I had been the kind of person who would start a jigsaw puzzle of a lady on a beach and just sort of leave it there after a week of intense infatuation. I’d finish the face and never get to the torso, let alone the seagulls and that person drowning in the distance. Jack in a Box was different. I loved making it and was constantly learning new things from episode to episode. It helped that people kept watching. That first episode garnered the most views by far, but after that enough people stuck around and shared it with others, that it felt right to keep making episodes for a while. Views weren’t really important to me. I wasn’t putting advertising on the episodes or making any money per click. My audience wasn’t gigantic, but it was loyal, supportive and kept on watching through the end. The timing was right, and I was able to engage a diverse and wonderful audience. It wasn’t just theatre people watching. It wasn’t just people with beards and their admirers. It wasn’t just my mother and aunts. It was real live strangers! Thank you, Facebook.
The whole experience was like my own little grad school. Through the series I grew as an actor, director, creator, collaborator and most importantly, writer. Prior to Jack in a Box I had only written material for myself. Dialogue wasn’t something I focused on, I mostly wrote monologues. I was very comfortable with my voice, but wasn’t sure if I could write for others. I was happy to find out I was wrong. I used the series not only as a way to explore writing for others, but also create opportunities to work with people I admired. People who made me want to write for them. People who made me laugh so much we’d have no choice but do multiple takes. Every role in the series was written for the actor that is seen on screen. I am so thankful and honored that none of them said “no.” I could write an individual essay about each and every one of them. Just go to the cast page on the Jack in a Box website, look ‘em up and I dare you not to become their fan. They are all brilliant, funny, generous New York Actors and terrific people. I’m lucky to have worked with all of them. Casting is crazy important, and I lucked out in that department.
The liberating (and also at times frustrating/limiting) thing about creating my own series for the web is that there was no one to answer to but myself. I’m not a very tough boss. I’m not super rigid. Yes, I’m particular and know what I want, but I gave myself a lot of breathing room. If I needed to not write so I could watch a Real Housewives Marathon, for better or worse, I’d let myself not write. If I wanted to sing like Ella Fitzgerald to my cat during the credits? Go for it, Me! If I wanted to take Jack away from his job for an entire season? Why not? Do it! If I didn’t want to explicitly address Jack’s sexuality until the third season? No presh. We all know anyway. There were no executives or networks giving me notes. There was no chance of being cancelled. I didn’t have to worry about advertisers. I could take the story wherever I wanted to. I could create my own deadlines. No one was saying “No.” That also meant there was very little structure to abide by. Structure is helpful, so I’d attempt to create some. I’d give myself a specific challenge for each season. The first season’s challenge was: “Um. Figure Out What The Hell You Are Doing.” From there on out it got a bit clearer. Second Season: “Jack Outside of Work.” Third Season: “Jack Back at Work, Mix Personal with Professional.” Fourth and Final Season: “Can Jack Be Happy?” That last season was hard to write. I know the answer, but I’ll let you watch and decide.
While I am glad I made the choice to end the series in its existing form when I did, I still miss Jack a lot. Luckily, I am a lot like him so he’s always there. Or rather, a happier version of him is always there. And I know no matter where my career takes me as a writer/actor/creator, I will always have Jack in a Box, an accidental journey I couldn’t be happier to have started. Without immediately realizing it, I created the exact kind of show I wanted to make with zero compromise. That luxury was afforded only because I decided to make my show on own my terms on the World Wide Web. Now, don’t get me wrong, I look forward to the day when I am told what to do by an executive or network. I await it with open arms. That is something I’d never known I was open to if I hadn’t spent almost four years telling Jack’s story and figuring it all out as I went along, for all the Internet to see.
When I decided to end Jack in a Box, people asked, “Would you do anything differently?” I’ve been thinking about this a lot lately. And the answer is: Yes. There are four episodes where I don’t wear gingham. That drives me crazy. I’m not sure what I was thinking. I’d replace those four shirts with gingham and fire myself from the wardrobe crew.
People also ask, “What’s next?! I can’t wait to see what you do next!” Me neither, friends. I’m figuring it out, but one thing is for sure: I’m prepared to turn that initial panic into inspiration.
–Michael Cyril Creighton
Michael Cyril Creighton is an actor and writer based in NY. He created/wrote/starred in the web series Jack in a Box. TV Credits: FX’s Louie, NBC’s 30 Rock, Logo’s Jeffrey & Cole Casserole and an upcoming episode of Netflix’s Orange is the New Black. On the web, he’s been seen in The Burg, Very Mary-Kate, High Maintenance (wrote and guest starred in the episode entitled “Helen”), Downsized, VH1’s Best Night Ever, and others. On stage he has originated roles in Blood Play, Buddy Cop 2, You’re Welcome and Cape Disappointment (all with The Debate Society) and Joshua Conkel’s MilkMilkLemonade.