The big and crazy scheduling snafu at this year’s IFFBoston came on Sunday night, when The Little Hours (which we reviewed at the time) went up against comedian Demetri Martin’s directorial debut Dean, which had gained a huge interest boost after it picked up the Grand Jury Award at Tribeca.

Those who chose the former made the right choice, as for all of Little Hours’ issues, it was still an interesting and intriguing watch, feeling truly modern even though it had throwback aspects and an occasionally rocky script, and it looks like a straight-up masterpiece in light of the alternative. Dean is an achingly mediocre film, the kind of low-budget capital-I “Indie” that circulated widely and embodied certain “intellectual” comedy until the Apatow frat house rented out the place next door and wreaked enough lovable havoc that the “respectable” elements of the genre had to move out to the suburbs.

Dean (Martin) is in crisis, and with good reason: His mom recently passed away, and he’s taken the loss hard. A moderately successful illustrator, living near his father (an utterly wonderful Kevin Kline) in New York City, he finds his work slowly being consumed by images of death (such as the Grim Reaper reaching out towards his caddy for a new scythe in a golf bag full of them), and he feels stuck and sort of empty, having recently split with his fiancee as well. When his father announces to him that he’s going to be selling Dean’s childhood home, he kind of loses it a little bit, and decides he needs a bit of a change. A chance encounter with a friend at a wedding inspires him to go out to LA, and avoid all the trouble and craziness back home, though he’s a little put off by the so-called “creatives” he encounters all throughout the city. One night, he goes to a party and meets Nicky (Gillian Jacobs), a funny and interesting young woman who takes a shine to him, and they begin an extended flirtation. On the other side of the country, Dean’s father falls in love with his realtor (an excellent Mary Steenburgen), and begins to wonder if he will, in fact, be able to move on from the memory of his wife. Though separated by a whole continent’s worth of land, the father and son have similar experiences, and learn valuable lessons about the nature of grief and the power of love.

Dean’s arc is surprisingly empty — the entire movie could have been set in Manhattan, and probably would have learned the same lesson given a small amount of time — and his relationship with Jacobs’ character is doubly-so, as Martin mistakes the initial bit of eccentric attraction to be the defining aspect of their interactions. His story is dramatically unfulfilling in a number of ways, and it’s also undermined by a dramatically etiolated performance by Martin. The humor, which attempts to caulk over the cracks, is a pale imitation of the director’s true gift as a stand-up and as an illustrator. It also can be shockingly cruel at some points, with Dean’s friend and LA host Eric (Rory Scovel) getting a number of weird jokes thrown in his direction for a) caring about the cat he owns and b) being slightly awkward in a car towards one of Jacobs’ friends. Dean plays off Eric’s awkwardness as him having Asperger’s Syndrome, and it’s just a mixture of vaguely offensive writing and the heavy flaws within the tone the film takes towards Dean’s actions.

One has to wonder what a slightly more cynical movie would have looked like; instead of presenting its man-child main character as a ne’er-do-well creative who is somehow more honest and pure than the people around him, perhaps the film could own some of his flaws and looked a bit deeper than the surface-level gags we’re given about how Silicon Valley bros suck and how bitches be crazy. Kline fares significantly better, and the universal criticism this film will get is that Martin doesn’t know how to utilize his film’s strongest asset: The brilliant chemistry between Kline and Steenburgen. And by “doesn’t know how to utilize,” I mean “doesn’t scrap everything in the script with the word ‘Dean’ in it and hone in on a realistic and beautiful set of performances that are limited to less than 20 minutes because of reasons.”

On a technical level, there’s really nothing to write home about. Dean’s competently shot and edited, sure, but it’s not nearly as interesting as The Little Hours in any surface way. It features a soundtrack full of the kind of aching acoustic retro-pop that someone who wanted to be like Wes Anderson would put together without realizing the work that goes into making those cues truly memorable. And yes, Martin’s drawings can often be amusing, but his work hasn’t jumped in any meaningful way from the Comedy Central special your ex-girlfriend and you watched back when Dane Cook was considered a Hollywood leading man by the studios and Ashlee Simpson was still famous for something besides lip-synching.

That might explain the appeal of something like Dean to certain audiences: This twee quirkfest feels like a throwback to an era that we’re typically not supposed to be nostalgic for, given all the massive psychic traumas that happened to our culture around then but are going to be, anyway, especially as our generation gets older (9/11 and the ensuing overseas conflicts ranked chief among them). Yet it’s fair to suggest that a film like Garden State’s most memorable assets were its cast, in which it got in on the ground floor on a number of transformative careers (Natalie Portman, Peter Sarsgaard), and its soundtrack, which is pretty and vacuous like Dean’s is, but was full of contemporary music. The problem with Martin’s film is that we’re older now, and as anyone who’s tried to watch The Goonies after hitting puberty and can’t see why they gave a shit anymore can attest, times and tastes change.

Follow Nick Johnston on Twitter @onlysaysficus.

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