Art imitates life for Ropes & Gray partner Robert Skinner who created and stars in a new semi-autobiographical film about a Big Law attorney who struggles to balance his busy job with a secret side gig—performing a one-man cabaret.

Skinner, a litigator, enlisted former Ropes & Gray colleagues along with actors to make the mockumentary comedy, “Day Job,” which had its premiere earlier this month.

For almost a decade, Skinner has been performing his own one-man show across theaters in Boston and New York while also practicing law full-time at a major global firm. The experience inspired him to make a movie about an attorney much like himself trying to figure out just why he feels the need to take to the stage.

“I’ve been blessed with this great family, and health and career and yet something is still telling me I should do more, and be more and have more, obviously I’m not alone in this,” Skinner said. “I thought, ‘Why am I doing this show, what motivates me to do this, to jam this in in the rest of my otherwise busy and full life?”

‘Day Job’

After four years in production, the film previewed to an audience of nearly 250 cast, crew, family and friends ahead of what Skinner hopes will be a successful launch on to the festival circuit in the year ahead. Directed by former Ropes & Gray associate David Baron, the film features excerpts of Skinner’s cabaret show, interspersed with a story about how a big firm lawyer’s theatrical aspirations bump up against the staid world of Big Law. The film finds humor in how the lawyer, as well as his wife, protege and boss deal with it all.

Skinner’s decision to take his work from the stage to the big screen was similar to his decision to start his cabaret show, “The Midlife Crisis Cabaret” years prior.

“It’s a creative outlet that scratches an itch that I can’t quite reach in the courtroom,” Skinner said. “But in another way, I think it’s also a way of looking hard at a question I can’t figure out about myself, which is what the hell is that voice in my head that says ‘not enough.’”

But unlike his on-screen counterpart whose cabaret moonlighting draws the ire of law firm management, Skinner’s career in theater actually began at Ropes & Gray where he would put on skits and other performances internally to the applause of his colleagues.

On Stage

Skinner first joined Ropes & Gray in 1994 and has spent his entire career at the firm representing investment advisers and others in the financial services sector in securities litigation and other business disputes, minus a short stint as interim chief corporate counsel at Affiliated Managers Group, Inc. in 2014.

But when he turned 40 a decade ago, Skinner decided he was ready to take the stage.

“I thought I’m having so much fun with this why don’t I rent a theater and write a show about other things and see where it goes,” he said. And so he did, performing his cabaret while maintaining his practice for nearly a decade when he decided to write his own film.

Skinner wrote and funded the project himself and arranged for the cast and filming locations. This level of autonomy also allowed him the opportunity to set the film aside or pick it back up with the ebbs and flows of his busy practice, he said.

He also turned to some of his former Ropes & Gray colleagues to round out the cast. Former Ropes & Gray associate Kurt Kusiak stars as Skinner’s problematic managing partner and the film features an appearance by longtime Ropes & Gray litigator, now retired partner, John Montgomery.

And while he doesn’t want to give away the ending of the film, Skinner said the troubles faced by his on-screen persona come to a head in a surprising way. But he promises that the audience is in for laughs while looking at a serious question, Skinner said, “which is, why are people like me with so much going on in their lives still driven to have these side passions that sort of scratch some itch that otherwise isn’t touched?”