It’s hard to sell a movie when you can’t seemingly tell the audience what it’s actually about (just ask "The Cabin in the Woods").

A brief box office autopsy could find plenty of reasons why "The D Train" scored a mere $447,524 at the box office this past weekend – good enough for the fifteenth worst wide release in history, finishing just ahead of "The Oogieloves in the Big Balloon Adventure." IFC’s inexperience of handling a bigger release without the buzz of a limited release was likely a poor symptom. With 1,009 theaters, the film marked the indie distributor’s largest opening weekend rollout, but consumer awareness wasn't apparently grown to match.

However, the ad campaign – which was oddly secretive in the few moments it bothered to show up – was likely the big gaping cannonball-sized cause of death. The trailers and posters sell a generic comedy, with a cool guy and a dorky dude bonding over drunken hijinks and maybe learning some lessons about themselves and each other along the way. Which it is … until the movie steers its bromance down a dark path of drunken despair, obsession and self-loathing – all while Mr. Mister, Foreigner and other ‘80s synth croons on the soundtrack.

No wonder the ad team didn’t really know what to do with "The D Train." Hell, I’m not even sure what to do with it. All I know is that the mix of comedy and drama is simultaneously amusing and cringe-inducingly awkward. So … pretty much just like my high school days all over again.  

Jack Black stars as Dan Landsman, the dweeby self-appointed chairman of his high school alumni committee and exclusive holder of the almighty Facebook group administrator password. Neither of these attributes – nor his numerous unadopted attempts at nicknames, like D Money and D Fresh – make him any cooler to his fellow committee members (including Ned Schneebly himself, Mike White!) who hit up the bars after meetings sans our sad schlub Dan. They don’t help snag many alums for their upcoming lame duck of a 20-year reunion either.

Inspiration soon strikes D Smoove, however, in the form of a late night Banana Boat TV commercial. The star of the ad is none other than Oliver Lawless (James Marsden, Cyclops in the "X-Men" movies), who, as his last name would suggest, was the coolest dude in their high school. He’s made it big (or at least suntan lotion spokesman big), and Dan’s sure that if he can convince their class’ studly star to come to the reunion, everyone else will follow. "If David Schwimmer goes, everybody goes," is Dan’s laughably unhip reference of choice. 

Under the guise of a fake business meeting, Dan (complete with soul patch) jets off to Los Angeles – along with his out-of-date boss, played by the indispensable Jeffrey Tambor – to talk Oliver into heading back for one more night of high school. And over the course of a few heart-to-heart chats and more than a few boozed-up, coked-up nights on the town, Dan manages to finagle Oliver into attending the reunion. The two even brew up a little bromance that, well, um, I guess put on your spoiler (but not really spoiler) earmuffs?

One they drunkenly consummate.

After casually pushing your typical movie bromance to its logical extreme, writer-director duo Andrew Mogel and Jarrad Paul launch Dan into new depths of confused desperation. Dan returns home with Oliver RSVPed yes for the reunion and the newfound adoration of his committee members – not to mention about a head full of questions. Are he and Oliver actually bros now? What did Los Angeles mean? And how the heck is he going to tell his boss that the hotshot they struck a huge deal with during their trip was just his former classmate in a suit, playing a role that went too far?

A darkness-tinged cringe-full comedy doesn’t exactly sound like the ideal vehicle for Jack Black – shockingly playing his first on-screen role since 2012’s "Bernie," not including his cameo in last summer’s "Sex Tape," a film which, according to IMDB, existed. Buttoned up is admittedly not his best form; it always feels like the actual Jack Black is just waiting to rip through his comparatively milquetoast outer shell, with his brassy tics leaking out here and there. That being said, he still delivers a shiftily funny performance, doing his best with the wildly fluctuating emotions of a lamely insistent guy finally getting a taste of the cool acceptance he’s always wanted – and then some – but totally insecure about what to do now or how to keep it.

The real star, however, is Marsden as the object of the movie’s obsession. And deservedly so, considering how effortlessly smooth and smolderingly magnetic his performance turns out. When he’s on screen – or merely talking, as he’s introduced back to the camera – he feels like the coolest guy in the room. He’s cavalier and unaffected … and just aloof enough to give off the vibe he’s better than you (I enjoy his slightly baffled inflection to being put on hold during phone calls). That is, until he and Dan run into Dermot Mulroney, and Marsden perfectly reveals all of Oliver’s stammering insecurities, that he’s just as yearning for acceptance from the popular kids as Dan. In the words of Ben Folds, there’s always someone cooler than you – and he’s still just the Banana Boat guy.

That scene is pretty much on point with the rest of the bizarrely dark and uncomfortable tone of this story of two sad, disappointed dudes, latched to each other and the past (Dan fittingly works in an office trapped a decade or two back in time, complete with wood paneling and a Tab machine). The characters' behavior and situations are consistently landing somewhere right in the middle of funny and just kind of tragically pathetic. There’s still certainly some laughs to be had from all this, but many of them come lacquered in a thick layer of awkwardness, discomfort and just plain ol’ high school scarred sadness. Even the synth-happy score seems to occasionally ping with uneasy, moody melancholy. And yet through all of the tough humor and odd tonal sways, it all stays unexpectedly engaging.

Much like Black’s performance, you’re always kind of waiting for the film to blow into something a bit funnier. But nevertheless, it’s at least still amusing with some strong laughs cutting through the oddly compelling discomfort – namely a hilarious sequence where Oliver gives blasé threesome advice to Dan’s 14-year-old son (did I mention the movie’s awkward?), ruining lawn chairs in the process. Marsden and Black make some entertaining sparks together, and they’re surrounding by a strong cast of bit players (Tambor, Kathryn Hahn, Henry Zebrowski – aka Alden "Sea Otter" Kupferberg from "The Wolf of Wall Street") that each score a laugh with minor characters.

"The D Train" may never quite completely coalesce. Discomfort comedy tends not to score the biggest laughs, and the characters’ constant emotional shifts – and the movie’s constant tonal shifts – make for an odd ride. But much like high school, it’s an awkward ride that’s mostly worthwhile.