Dean is not, as it purports to be in nearly all of its marketing material, a “comedy about tragedy.” It’s more along the lines of a middling post-mumblecore dramedy about Demetri Martin wish-fulfilling himself into bed with Gillian Jacobs.
Granted, that wouldn’t sell as well on the poster.
It’s not a comedy due simply to it not being very funny. It doesn’t actually seem as though Martin, who wrote and directed Dean in addition to starring as its titular character, set out to make an especially funny film. Throughout, Dean’s characters are constantly doing “bits” with each other; every character in this movie has a swing at a “bit” or two. Not a one of these “bits” are funny, they’re more like a thought you might consider voicing to a friend before realizing that it’s not worth saying to begin with and then not saying it. Watching Kevin Kline, here playing Martin’s dad, do a dumb bit with a real estate agent is simply no fun, I tell you.
There are some laughs in Dean, particularly whenever its lead character’s (and yes, I will keep referring to Dean as some variation on “Dean’s lead character” in case the distinction between the film’s title and the character it refers to isn’t made entirely clear through italicization alone) often-morbid comic drawings show up on screen. The character, Dean, is a comic illustrator working on his second book collection of artwork. The drawings are, in fact, inspired, something I wish I could say about the movie surrounding them.
Dean isn’t really about tragedy either, notwithstanding the fact that the film’s premise rests on the death of Dean’s mom (and Kevin Kline’s wife). The dead mom is barely mentioned, and while Martin clearly believes that his portrayal of a Zach-Braff-in-Garden-State-esque-saddie conveys his grief, it’s just not enough to claim to have made a movie about the grieving process. One closing monologue about a dead mom does not a tragedy make.
Instead, Dean is about Martin as “Dean” (but really as Demetri Martin) being a klutzy, socially inept manchild but also, inexplicably, incredibly attractive to the likes of Briga Heelan and Gillian Jacobs. He first spots Jacob’s character, Nicky, from across the room at a party (she immediately makes eyes at him), and proceeds to fall flat on his face and leave the room. But Nicky apparently finds his fall charming enough to later approach and flirt with him, tolerate his creepily stalking her around the rest of the party, and eventually get his number. Then, just scenes later, they’re in bed together and he’s waking her up in the middle of the night to tell her that he’s falling in love with her. Their relationship at no point makes very much sense from a character or pacing standpoint.
Dean’s protagonist also has a buddy named Eric, played by Rory Scovel, who is a pick-up-artist with a cat and a heart of gold. He spends the movie hilariously “negging” attractive ladies and saying things like “there are so many hot women [in L.A.] and a lot of them are desperate which is really… nice.” So.
Beck Bennett shows up for an extended sequence playing a character straight off of HBO’s Silicon Valley except with nothing funny to do or say. The one lesson that really should be taken away from Dean, as a matter of fact, is that Mike Judge and co. should book Bennett as a recurring character on that show because he’d fit right in, and with better material, be hilarious.
Two incredibly annoying components to this film: its soundtrack and its excessive use of split-screens. The split-screening speaks for itself, really, as the constant use of the device is grating, headache-inducing, and not remotely successful in the twee sort of way it was obviously intended. The interminable soundtrack is a non-stop barrage of indie-pop and acoustic guitar numbers that really emphasize Dean’s ambitions as a tonal blend of Garden State and Juno.
Early in the movie, Dean (the character) bombs his best man speech at his friend’s wedding. The scene is excruciating (like much of the “hoo-boy is Dean ever awkward” stuff in this movie) and not in a good, Curb your Enthusiasm sort of way but in a “Christ, I feel like I’ve seen this a million times before and not once was it particularly funny” sort of way. As cliché as it is to say, the scene really is analogous to the movie as a whole. Martin has gotten up for his big swing as a writer/director/star and straight-up bombed.
I like Martin, and his performance here isn’t even all that bad, but I wish he’d made a more interesting/distinctive/original/funny/mannered/stylish/meaningful/worthwhile film. I wish Dean was better.