There are a lot of films that bear the signs of having been kicked around a long time before they ever made it to the big screen. This is particularly true with indie films, which struggle to even get completed, let alone distributed; by the time they finally make their debut at film festivals, they’re working off of scripts that are sometimes a decade old or more. Sometimes, it doesn’t make much of a difference; certain stories are timeless, after all, and they make the transition without too much difficulty. Others, though, end up taking a pretty rocky road, and whatever their other qualities, come off as artifacts of a cinematic age that has long passed.
Such a movie is Ned Crowley’s Middle Man, the second that I saw at this year’s Chicago International Film Festival. Middle Man stars Jim O’Heir, who, though best known as human punchline Jerry Gergich on the NBC sitcom Parks and Recreation, is actually a 30-year veteran of the rich Chicago improv comedy scene. That’s where he met Crowley, who wrote the script for the film a good twenty years ago and has been trying to get it made ever since. It makes perfect sense in retrospect: not only does O’Heir’s part sometimes seem as if it was written for a much younger man, but the overall tone of the film is that of a King of Comedy for the Pulp Fiction generation. That’s probably the way it was conceived, and it frequently plays like a dark comedy of the mid-1990s. Not that there’s anything wrong with that, of course; some of my best friends are dark comedies of the mid-1990s. But it’s one of the handful of nagging qualities that kept Middle Man on the level of a good solid comedy and away from being a greater success.
O’Heir plays Lenny Freeman, an affable but lonely schlub who, after getting a small inheritance from his dead mother, decides to abandon his go-nowhere office job and make a go of it as a standup comedian. Lenny has some definite Jerry-style qualities: he’s obliviously cheerful, he thinks his co-workers like him more than they actually do, and he’s blind to his own shortcomings, the largest of which is that, like many other would-be comedians, he’s just not funny. His mother raised him on a diet of old-time radio comedies, so his material consists of ancient gags that aren’t so much dad humor as great-grand-dad humor; and worse still — since a lot of that stuff is genuinely funny — he doesn’t have anything original, or the ability to deliver it in a way that doesn’t sound like the kind of thing you’d hear from a friendly but corny bus driver trying to alleviate his boredom. So we know from the outset that Lenny’s not going to make it on his own merits. But that changes when he happens to pick up the wrong hitch-hiker — sinister drifter Hitch, hammed up to a greasy shine by Andrew J. West — who sees him as the key to settling old scores and erasing bad debts.
This is all pretty familiar stuff, but it takes an interesting turn: after Hitch commits a gruesome murder, Lenny helps him cover it up — only to confess to the whole crime that night during his stand-up set. Lenny had previously bombed, but the dry recital of his bloody deed, peppered with a few wry observations that he obviously doesn’t intend to be funny, turn out to be a huge hit, and every time he does something awful and owns up to it, his reputation as a stone-faced comic dabbling in the darkest of dark humor grows. It starts to look like the more bad things Lenny and Hitch do, the closer they come to realizing their show-biz dreams; Lenny unseats the local ruler of the stand-up roost (the enjoyably loathsome Josh McDermitt) and even manages to attract the attentions of a beautiful, sweet young waitress (ubiquitous character actress Anne Dudek of Mad Men). We know it won’t last, and it doesn’t, eventually ending in a bleak inversion of King of Comedy‘s most critical scene with a much higher body count.
Middle Man doesn’t stick the ending, and only partly because it seems to have been written for an era with different tastes in comedy. It also goes on a bit too long, and West isn’t quite strong enough to carry the amount of screen time he’s given. But it succeeds on a number of levels, the biggest and most important of which is that it’s pretty funny, and has in O’Heir a gifted comic actor who can do all the heavy lifting he needs to in order to sell us Lenny Freeman. It’s got a few inventive directorial touches, although that should be qualified by the reiteration that it would have seemed a lot more impressive in 1998 than it does in 2016. One of the oddest — and most appealing — aspects of it is its setting: although it was filmed in the southern California desert, it takes place in the fictional but fully realized nowhere town of Lamb Bone, Nevada, just close enough to see the lights of Las Vegas but far enough away that everyone in it knows they’ll never get there. It’s one of those creepy little locales that has its own internal logic, so that you’re more than willing to accept that a tiny flat patch in the middle of the road somehow has a thriving comedy club — and it also allows you to come to an immediate understanding that Lamb Bone isn’t really a place at all, but a reflection of Lenny’s personal hell.
It’s tough to know what to do with a movie like Middle Man. It doesn’t really have enough heft to make a strong feature film, and it’s not packed with wall-to-wall laughs; it struggles to bear the weight of a full-length movie. But there’s too much happening for it to be a mere sitcom-length short, and it would be a shame to see something with this much going for it to just disappear. In that sense, it’s near-perfect festival fare, a fun and edgy palate-cleanser between more ambitious projects; I’d like to hope that it’s got a chance to find a wider audience on one of the streaming services, which more and more seems like the natural home for things like this.