Martin Donovan is one of those “that guy” character actors that’s popped up in countless projects over the last three decades from playing Al Pacino’s partner in Insomnia to a DEA boyfriend on Weeds. But for anyone enamored with talky 90s indie-films, he’ll always be remembered as one of director Hal Hartley’s most memorable muses. Now Donovan has made a shift to becoming a writer/director and his film bares the distinct mark of Hartley’s meticulously crafted dialogue-driven character studies. Donovan doesn’t quite have the originality or spark of his presumed directorial mentor just yet, but his film is an intriguing debut for the potential new filmmaker. It’s a subtle, desperately dry dark comedy with thriller elements, a surprising amount of insight, and entertainment borne from trapping two unique characters in a room together and watching them talk.

Perhaps inevitably, Donovan takes on the lead role himself. He plays Robert Longfellow, a once promising playwright now on hard times while stumbling through middle age. The former critical darling turned into a whipping boy on his latest disastrous play and given that he put up most of the money for the production himself, that’s a bit of a pickle. So, Robert makes a sad journey back to his hometown of Los Angeles, looking to spend a little time with his mother (the much missed Katherine Helmond), pick up some hack screenwriting work for cash from a sleazy producer contact (Julian Richlings) that all good writers have, and visit an old flame turned movie star (Olivia Williams). Longfellow arrives depressed, but things only get worse in LA, as he awkwardly reverts back into childhood rhythms while staying with his mother and finds discomfort whenever digging up the past with former friends and lovers.

The only thing he has to push away the overwhelming sadness of his life comes from knowing things at least turned out better for him than his old high school buddy Gus (David Morse). Even though he’s in his 50s, Gus still lives with his mother, forever pissed off that he couldn’t join the army and drowning his sorrows in six packs and joints that he constantly invites Longfellow to get in on. Of course, the writer refuses until one night Gus shows up to press the issue with a gun and a night of drunken catch up turns into a hostage situation with police and SWAT teams surrounding the house while Gus and Longfellow awkwardly share stories while trying to ignore the “being held at gunpoint” thing.

The rambling, sad sack comedy set up to the kidnapping is intriguing and darkly funny with Donovan deadpanning through depression and actors like Williams, Richings, and Helmond getting to establish nice lost soul characters around him. Donovan has always been a generous actor who grounds scenes while letting his co-stars to the scene stealing and that’s his approach here as well, playing the anchor. The whole movie builds up to the kidnapping, which essentially plays out as a one act play between Donovan and Morse that is easily the best part of the film. Morse has a knack for playing big screen bad guys, but Gus isn’t really one of them. In many ways he’s the saddest and most empathetic character in the movie, a lazy man who filled the holes in his life created by a lack of talent, intelligence, and ambition with various mind-altering substances. He’s a sad victim of society and self-destruction now and after shooting a convenience store clerk to settle in with Donovan, things get interesting.

The pair chat about anything other than the kidnapping. Donovan’s broken man Longfellow comes off as selfish and snobbish, seemingly unaware of the luck and good fortune of his success. Morse’s criminal Gus is more of an innocent, undereducated, classless, and in desperate need of any sort of companionship and support. He finds it briefly with Longfellow and their spiraling conversation covers everything from issues surrounding US war tactics to chats about celebrity worship and weirdly, improv theater games that hilariously reveal Gus’ innocence and simple, sad, unrequited needs. It all builds towards a moment that explains the title and reveals Donovan the filmmaker at his most pretentious. There are times where his guiding hand as writer/director can feel heavy handed, forcing his endlessly thought out ideas through obvious screenwriting motions. Yet, the overall impact of the subtly comedic tone, the incredible ensemble performances (especially from Prose), and personal reflection is impressive. Donovan still has plenty to learn about being a director and storyteller (his sense of cinematic visuals is practically none existent), but there’s enough that works here to suggest he’s got a future. Donovan has created a film that works as both comedic/suspenseful entertainment and as a means of communicating thoughts and ideas, all focused through he joys of watching flesh and blood actors dig into real characters with minimal spectacle. Collaborator may be a flawed and minor movie, but taken on its own low key terms can be a really interesting experience.