Nothing says pathetic loser quite like giving one’s self a cool nickname and hoping it sticks among friends. In what becomes somewhat of a running joke in The D Train, that’s exactly what Dan Landsman (Jack Black) does in his desperate attempts to overcome his lonely loser high school legacy. But as expected, calling himself “D-Fresh” or “D-Nice” does little to make up for his being known as one of the uncool during his high school days.

As the film opens we learn that Dan is the self-appointed chairman of his high school’s 20th reunion committee, a title under dispute by the organization’s other members, but one that Dan claims is rightfully his since he has sole possession of the committee’s Facebook page password. It’s this disillusioned, self-loathing character around which filmmakers Andrew Mogel and Jarrad Paul build their film with hopes of tapping into that sympathetic side of everyone who struggled through those awkward high school years. The problem lies with the fact that Dan is a despicable, lying, narcissistic lunatic with as many endearing qualities as nails on a chalkboard. He’s not a good character from which to build a lovable underdog and, as a result, their film doesn’t garner the results intended.

Naturally, Dan believes turning his class reunion into a huge hit will make him popular among his fellow committee members, who lie to avoid post-meeting beers with him. So when he spies former classmate Oliver Lawless (James Marsden) in a national Banana Boat commercial, Dan sees it as his opportunity to take the reunion over the top, but more importantly, as a way to put the attention on himself… if he can only get the once-admired jock to return to Pittsburgh for the reunion.

It would have been so much easier for Dan to take a few days off from work and fly to LA to convince Oliver to attend the reunion. But then we wouldn’t have a movie, would we? Instead he lies to his boss (Jeffrey Tambor) with a cockamamie story about a hot lead for a potential client in California, then also lies to his wife (Kathryn Hahn) about where he’s going, and upon his arrival in LA, he even lies to Oliver about his own personal success and his self-serving intentions. As expected, Dan’s ruse comes apart in the most disastrous way possible during the middle of the reunion party.

It IS possible to bring an audience around eventually to seeing past a character’s flaws and embrace a film’s well-intentioned message. In fact, Black did it with his despicable, murdering Bernie Tiede in 2011’s Bernie -- and it was a beautiful thing to watch. But The D Train’s messy script and poorly-written characters make it impossible for us to, even for a minute, ask ourselves how far we would go to be popular.

There are many hilarious moments in The D Train and most of those involve Black and Marsden on the screen together. A night of wanton, drug-fuelled debauchery as the boys hit the town ends in the much-talked-about “twist” that feels as out of place as it is uncomfortable to watch. Any moments of hilarity are always quickly forgotten when the next head-scratching scene comes along with another clunky emotional shift and jarring structural inconsistency.

The D Train’s message that we don’t get a second chance to live down our high school reputations is an admirable if not wholly original one. The filmmakers clearly went for dark and edgy, a decision to be commended, but without anyone to root for, this train runs out of steam before it even leaves the station.

(Released by IFC Films and rated “R” for strong sexual material, nudity, language and drug use.)

Review also posted at www.franksreelreviews.com.