In last week’s 30 Rock season premiere, Liz “Cranky Sue” Lemon was, all of a sudden, happy! Fans saw her skipping with animated birds and smooching on a mystery man (James Marsden).
It was about time. Sitcoms about cranks have two options: cling relentlessly to the joke or allow characters to grow. Michael Cyril Creighton, creator and star of the critically acclaimed web series Jack in a Box – who also had a hilarious turn on 30 Rock – opted for the latter.
“I tried to make him a little happier this past season, which some people weren’t jazzed about. But I needed to do it as a challenge to myself, because it’s really hard to write that character happy…I thought it was time,” Creighton said in an interview.
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“We’ll see how long that happiness lasts,” he added.
Unlike his character Jack, Creighton has had a lot of reasons to be happy. After Jack premiered in 2009 it quickly developed an enthusiastic fan base and won a top award at the New York Television Festival. A year later, when the New York Times decided to start covering web programming, readers alerted writer Mike Hale to Jack. Jack eventually got Creighton membership to the Writers Guild of America East, and this month the Guild honored him with a nomination for best original web series, alongside Aim High (McG/Warner Bros./Cambio) and Downsized (from fellow indie creator Daryn Strauss).
“It’s amazing…It feels good because there’s a lot of stuff on the web, and it’s hard to make an impression,” he said. “I’m constantly humbled and surprised when I come out with something new and people still watch it.”
Creighton is halfway through writing the fourth and final season of Jack. As the series approaches its finale, he is starting to reflect on its success, why many viewers stuck with the show through its two dozen episodes.
“I feel like the voice is pretty clear, and I’ve known what I was trying to go for from the beginning,” he said, adding that the show has improved over the years. “I think I’ve gotten better as a writer, as an actor, as a collaborator. The longer I do it, it’s starting to get stronger, just because of practice.”
One of his greatest challenges was making Jack relatable, since the character can tend toward sad and supercilious. As a writer, Creighton tried to make Jack’s most unlikable traits — petulance, mild disgust — understandable given the character’s ludicrous work and family life.
Like with every indie web production, making Jack in a Box is a lot of work, particularly in post-production, but Creighton keeps it as simple as possible. Most episodes take place in one location, which his collaborator Jim Turner, who also does the editing, shoots in a few hours.
The show has featured a terrific roster of guest stars and regulars, most of them Creighton knows from acting in New York. Two-time Tony Award nominee Mary Testa and fan favorite Katine Corrao (Good Neighbor Minute) regularly play Jack’s foils and instigators. Cycling through the show have been a robust cast of actors known for solid TV and web series work: Marylouise Burke, Jackie Hoffman, Randy Harrison (Queer as Folk), Becca Blackwell (Gay’s Anatomy), Patrick Heusinger (Gossip Girl, Royal Pains), Thom Woodley (The Burg, Greg and Donny), among others.
“I’ve had some good muses,” Creighton said. “It’s probably my favorite part of the whole series.”
Perhaps the biggest development of the past season was Jack’s new beau, Drew (Paul Thureen). For the first two seasons, the character stayed avowedly single, though Creighton believes most viewers knew he was gay. Jack’s singlehood made sense in the beginning, and Creighton didn’t want to push a romantic storyline before the character was ready.
“It wasn’t right for the story to have any love because he wasn’t able to,” he said. Writing a relationship was one way Creighton let the lead grow. “It just happened to happen when I needed to write it, and the audience wanted it, and Paul was available to play the part.”
Next up for Creighton are a series of guest roles on a number of web shows, including Timeless Seasons; Guards of Dagmar, the highly anticipated series from Anyone But Me scribe and 2011 WGA award-winner Tina Cesa Ward; and a possible role in Two Jasperjohns by Vinny Lopez.
While he’s sad to see Jack go, Creighton is eager to work on new ideas, including writing a television pilot. “I need to let this baby grow up and walk away.”
WGA award nominees will be honored on February 19. The fourth season of Jack in a Box premieres later this spring.