Beyond the red carpet of ‘Work in Progress’

Abby McEnany and Tim Mason have inspired much more than an impending cultural sensation with their new Showtime comedy series, Work in Progress. Besides earning a ton of critical praise, the duo represents a thriving reminder that Chicago is a great place for aspiring filmmakers to be.

The community-wide excitement was obvious during the series December 6 premiere at AMC Theatres. Filling the entire width of a corridor on the fourth floor, it generated a contagious kind of joy that spread far beyond the red carpet: Work in Progress is a win for everybody.

“The crew was as excited as the cast,” recalls Laura Roeper, a member of Studio Mechanics Local 476 and the show’s Property Manager. “I’ve never seen that … it was one of the happiest nights of my life.”

Roeper spent three years on Empire before joining Work in Progress. Every day on the set, she reaped the benefits of a commitment to inclusivity that “transcends so many boundaries.”

“A lot of the crew came from the advertising world and a lot of them came from the improv world, and there were no definitions on what our job descriptions were,” she explains. “Everyone on the crew did what they were supposed to, of course, but if there was something that someone noticed during a shot, we could approach (director) Tim Mason and make a suggestion. The only other director I worked with who did that was Craig Brewer on Empire.”

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Meet Abby McEnany
In Work in Progress, McEnany plays lead-character Abby, “a 45-year-old self-identified fat, queer dyke (IMDb).” Rolling through situations based on her own life, she encounters death, doubt, suicide and depression while becoming an altogether likable heroine. And that’s pretty much only the first episode.

Variety’s Caroline Framke describes the series as “nuanced and funny.” The Guardian’s Rebecca Nicholson says that it “marks the arrival of an important new voice.” Sun-Times entertainment columnist Richard Roeper declares that the show “should be one of the breakout new TV series of 2019-2020.”

McEnany worked long and hard to earn the praise. She spent a decade auditioning for Chicago’s venerable Second City before getting accepted, then introduced Work in Progress as a live storytelling performance at the organization’s iO Theater. When her friend and frequent collaborator Tim Mason persuaded her to convert it into a web series with him as director, she hired the first of many Chicago-based film professionals who came along for the ride.


Rewarding the crew
Tessa Films co-founder Lisa Masseur would be another cohort to sign on during the early days. Serving as Executive Producer for the pilot, which premiered at Sundance, she stayed on as a producer for the series and knew that great things were ahead.

“From the get-go, I never had any doubt that this would happen because of Abby herself,” she recalls. “Abby’s a magnetic person in real life, but on camera I cannot stop watching her.”

Masseur is also pleased, but not surprised, by the way that McEnany and Mason handled production and shared the rewards of their success. She has worked with each of them for years: McEnany has been involved in various projects at Tessa Films, and Mason is one of the directors on the company roster.

“They wanted a diverse cast and crew and they really stuck to that and went to great lengths to make sure it happened,” she says. “Virtually everyone who worked on the pilot was offered a spot on the show.”

Besides her obvious admiration for the people and the process, Masseur is also a true fan of the series.

“The first scene is great and fantastic, but if you only watch that you don’t get to know what the show is all about,” she explains. “It’s dark, and there’s heart, and it’s deep.”

The fantastic moments in the first episode include an unexpected casualty and a public swoon triggered by Saturday Night Live alum Julia Sweeney, who plays herself in the series. These kinds of traditional gags require a top-notch actor to be funny, and McEnany pulls them off like a modern-day Lucille Ball.

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Capturing the action
Work in Progress Cinematographer Michael Ognisanti is the man who captured the action. After collaborating on commercial projects with Mason for years, he has come to understand and anticipate the director’s style, which involves a lot of cross shooting.

“One camera capturing it one way and another capturing it from another angle,” he explains. “Tim has always been like this: he wants two cameras.”

The technique suited McEnany’s talent perfectly.

“Abby is an energetic onstage performer,” he says. “But we found a subtlety that she is able to convey on film — these emotions in the quiet times — that was really cool.”

His job was made easier by the “relaxed and family-type atmosphere” supported by McEnany, Mason, and Chicago film legend Lilly Wachowski, who had come on board as writer and producer around the time that the pilot screened at Sundance.

“On set, a lot of times, it can be contentious and stressful,” he continues. “Our crew was diverse and inclusive and everyone felt comfortable, which was important.” When that mentality comes from the top — from Lilly and Tim and Abby — it just kind of ripple-effects down.”

According to Periscope Post & Audio’s Mike James and Sam Wong, who handled dailies for Work in Progress, the positivity continues long after the cameras stop rolling.

“Even though we were not technically on set, it was a joy to work on,” says James. “They’re both super nice,” adds Wong. “Abby makes every single person she talks to feel like her best friend.”


Turning success into tradition
McEnany and Mason are not the first indie filmmakers to convert passion into success with help from Chicago’s film resources. Sam Bailey and Fatimah Asghar got a boost for Brown Girls from OTV. Bing Liu honed his Oscar-nominated documentary, Minding the Gap, through Kartemquin’s Diverse Voices in Docs program. Fawzia Mirza and Jennifer Reeder brought Signature Move and Knives and Skin to the screen after pitching them at the Chicago International Film Festival’s The Pitch Industry Days event. There’s also the tireless work of Free Spirit Media, Full Spectrum Features, Stage 18, and Chicago Media Angels.

So in that respect, Work in Progress is not unique, which is another cool thing about the show.

’Work in Progress’ premiered December 8 on Showtime, but the entire series is still available for viewing. To check it out, click here.