Demitri Martin makes cute, amusingly wry drawings: this was roughly all I knew about the comedian before I saw his directorial debut, Dean. And, sadly, it was pretty much all I knew of him after.
Dean is not, as one might have feared, a completely insufferable movie, but it is a completely insubstantial one. Competent, harmless, and even mildly charming (once in a while), it simply has no obvious reason for existing and nothing in particular to say.
Dean, which stars writer-director Martin in the titular role, purports to be "a comedy about tragedy." Dean—a young(ish) cartoonist, living in Brooklyn—is having a hard time moving on from the recent death of his beloved mother: he has a collection of her supportive voicemails saved on his phone, which he listens to obsessively, and images of Death (literally and figuratively) have begun creeping into every drawing he tries to make. Meanwhile, Dean's widowed father Robert (Kevin Kline) is trying to move on with his life. Robert wants to sell the family house—for which he enlists attractive real-estate agent Carol (Mary Steenburgen)—but this prospect alarms Dean, who impulsively flees to Los Angeles as an excuse to avoid discussing it. While in L.A., Dean takes a meeting with an obnoxious ad agency, hangs out with various friends and acquaintances, and cute-meets a woman (Gillian Jacobs' Nicky) who compels him to extend his stay. Eventually, without much actually happening, and without any particular epiphany, he goes home to make his peace with his father, and with his mother's death.
That's more or less the entire plot of the film. And if this summation sounds like an unconscionable spoiler, you have higher expectations for Dean than the film is prepared to reward.
In his first feature, Martin is a halfway decent director: he has clearly studied the mid-period works of Woody Allen very closely (even if he has completely overlooked their depth). As an actor, he is a bit of a presence-less placeholder: he is not blatantly terrible, but he is all surface, and self-conscious surface at that. (Watching him attempt to hold his own with Kline—or even Jacobs, with whom he has a disastrous lack of chemistry—elicits sympathy, but not much respect.)
The problem, however, is in the writing: it skates on the hipster edge of everything so lightly that it actually touches nothing. There are a few mildly amusing, Allen-esque lines. ("I liked you two together," Robert says, of the girl with whom Dean has recently broken up. "You should see us apart, though," Dean deadpans. "We're great.") But there is no textual weight anywhere to be found in the screenplay, and Martin is simply not enough of an actor to layer in the emotional content or insight he has neglected to put on the page. Dean's mother (voiced in recordings by Florence Marcisak) never comes into focus as an actual human being, and the mourning process both Dean and Robert are allegedly going through lacks both specificity and substance. We are told they are mourning, but we don't feel it, and they never really explore it. (There might have been a good movie to be made about the characters played by Kline and Steenburgen: their scenes are emotionally slight as well, but they at least give one the reassuring feeling that the grown-ups are talking.) Martin's drawings aside, the film has nothing to say about death, and no meaningful observations to share about parent-child relationships. Figures who move through the film have personalities, but not actual characters, and no one really grows, or learns, or changes.
In one of the first scenes of the film, Dean encounters a boy—about five years old—who is wearing the exact same outfit he is wearing. It's a hint that the central issue of the film is supposed to be Dean's man-child status, which is both insufferable—Martin comes across as being in his early 20s, but he is actually in his mid-40s—and never resolved. Dean is avoiding adulthood for most of the film, and by the film's end Martin has completely avoided dealing with what adulthood might actually look like. As a writer-director, he has utterly failed to dig, below the surface, for anything, relying instead on superficial feints and fleeting charms. It's simply not enough.
But the drawings are awfully cute.