Modern movie advertising is a fucked up game. If trailers don’t give away the entire plot of a twisty thriller or spoil the funniest bits of the latest comedy, they sand down the edges of anything unique until it resembles the same cookie cutter studio fare that gets churned out with disappointing regularity.

Ads for The D Train present a run of the mill mainstream laffer, with Jack Black playing yet another variation of himself named Dan Landsman, a forty year old man-child whose obsession with being unpopular in high school leads him on a cross country trip to visit former classmate-turned-Hollywood actor Oliver Lawless (James Marsden). Dan thinks if he gets Oliver to come to their high school reunion, he’ll finally be popular. It’s a fine if flat premise. From the trailer, it’s the kind of thing Will Ferrell might make between Adam McKay films to keep the lights on. If someone asked you to jot out the beats of the story based on nothing but a YouTube preview, you could probably sketch a coherent approximation. But the film has a trick up its sleeve.

A fascinating wrinkle in the relationship between Dan and Oliver sets The D Train apart from its low hanging fruit brethren. It’s been spoiled elsewhere on the internet, but the film’s second act takes a narrative risk that’s almost brave. The tonal shift could easily play like a weak joke, but it transforms the film into something else entirely. Without going into specifics, the film’s exploration of some murky dramatic material requires an ambition that comedies like this usually lack. It doesn‘t hit a home run, but co-directors Jarrad Paul and Andrew Mogel at least make it to base.

Dan and Oliver are flip sides of the same depressing coin. Dan can’t leave the past alone; Oliver is content to leave his glory days where they belong. Black plays Dan as pathetic to a fault, a lovable loser who fails to even be likable. He sits at his dilapidated office computer stalking his fellow reunion committee members on Facebook, where photos of their late night drinking sessions load at a painful dial-up clip. He’s jealous of his own teenage son for having a girlfriend at an age when nobody would talk to him. There’s even an ongoing gag of him trying to give himself nicknames that starts off barely humorous and devolves into tragicomic Travis Bickle territory.

In contrast, James Marsden delivers a vitality and charisma that his usual roles stifle, presenting a flawed but understandable portrait of a struggling actor who hides from the realities of his life with drugs and alcohol. He is the literal manifestation of youthful nostalgia, and every character he encounters from his past clings to him like a DeLorean that can get them back to a time before it all went wrong. You become as engrossed in him as the rest of the cast, and this attraction grounds the film’s otherwise difficult leaps of faith, forcing you to bond with Dan where you would otherwise be annoyed to the point of repulsion.

This well intentioned twist on Judd Apatow bro humor takes time to explore the hefty consequences of immaturity and stunted growth. Yet the film takes awkward farce to heights so uncomfortable and laborious that calling it a comedy seems unfair. It uses the familiar trappings of mainstream comedy vehicles to tangle with the sadness of lying, both to yourself and your loved ones, and the misguided preoccupation with being popular. The zany set-ups of the first act give way to messy results that give weight to the sobering turns of the plot, but there isn’t enough levity to keep you in your seat. The D Train aims high, but if you’re looking for a good belly laugh, you’ll have to settle for some stomach churning anxiety at the tangled web this “comedy” weaves.

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