Q&A Quickie: Web Star Michael Cyril Creighton, Packing Up Jack's Box

By: Brandon Voss

After three years and four seasons, Michael Cyril Creighton has decided to end his award-winning web series Jack in a Box. Creighton plays Jack, a cupcake-addicted struggling actor who must suffer a rainbow of fools while working in a theater box office — pure comedy gold inspired by the gay actor's own day job. Currently in rehearsals for a buzzworthy new play, Creighton unwraps what's next for him and his curmudgeonly online character. 

Gay.net: Was the Jack in a Box finale emotional for you?
Michael Cyril Creighton: Writing the last episode was the biggest challenge I faced during the four seasons. I certainly procrastinated. When I first started writing the final season, I had a lot of grand ideas about how I wanted to end the series: lots of guest stars, life-size cupcakes, explosions, one single tear, and a gun shot — that kind of stuff. But as I got closer to the end, a showy ending didn't seem right. Finally, I ended up sitting in a Starbucks one day and told myself I couldn't leave until I finished a draft of the series finale. That morning turned into an afternoon and I ended up extremely overcaffeinated and wildly emotional. Crying silently to myself while I wiped cake pop off my face. It was tough. In the end, the final episode ended up being something very simple, and I think very true to what came before. Sure, I'm sad to end the series, but I'm also real proud of what I have accomplished and how it ends.

Is this really the end of Jack in the Box, or is it like Cher's farewell tour?
It's the end for the forseeable future. Maybe I'll do a holiday special at some point. I have been working with an executive producer on a treatment for a half-hour version of the show, and I'm hoping to pitch that around soon. But for now my plan is to come up with a new idea and make that.
The finale is entitled "The Future," but Jack's fate is largely left up to the viewer's imagination. Have you imagined an fictional future for the character — 5, 10, 20 years down the line? 
I can't even imagine my own future 5, 10, 20 years down the line. I will say, though, that I'm not sure Jack will ever be truly happy. But maybe he'll surprise me. 

What can you tell me about your role in The Debate Society's production of Blood Play?
It's extremely different than Jack and most of the other roles I've played — which is why I love working with The Debate Society so much, because they always write me really wonderful roles that challenge what I and others think about me as a performer. This is my fourth show with the company. In the last play I did with them, Buddy Cop 2, I played an extremely stoic and gruff Midwestern cop in the '80s. In Blood Play I play a nice Jewish husband in Skokie, Ill., in the early 1950s. My wife — played by Hannah Bos, who's been seen as my BFF Millie on Jack in a Box — and I are new to the neighborhood and trying to make a good impression. It's a wonderful play, and I'm really proud to be part of it.

I loved your hilarious recent guest spots on FX's Louie as a contestant on the Big Brother-esque reality show-within-the-show. What was that experience like? Did you have a lot of interaction with Louis C.K.? 
I loved fake-stabbing that woman — that was a hoot. I actually didn't audition for that part. I had auditioned for the previous season a few times and then got a call in February offering me this role, and I think I literally squealed when I got the call. We didn't shoot until May, and that day was just amazing. My favorite interaction with Louis C.K. was when he sat next to me and said, "What's your character's name again?" I replied, "Gay Man. AKA Marvin." To which he replied something like, "Don't be offended! I wrote it with you in mind but wasn't sure what your name was. It was just a placeholder. Just play it like you." He was generous, funny as hell, kind, and yes, kind of dreamy. He spent time with me and made me feel really welcome and comfortable on the set. He treated everyone with a huge amount of candor and respect. He's a phenomenal director and a really nice man — everything I had hoped for and more. I definitely left that night wanting to make him a mixtape.

See all 31 episodes of Jack in a Box at jackinaboxsite.com. Creighton also stars in Blood Play, Oct. 3-27 at New York's Bushwick Starr.