There’s a dark joke at the core of War Dogs that’s so good it almost sustains this so-so comedy all on its own: What if the jerk Americans who got rich off the Iraq War were the same type of asshole bros who were the antiheroes of The Hangover? That’s essentially the thesis of filmmaker Todd Phillips, which is fitting considering he directed both movies, demonstrating in The Hangover and Old School a fondness for satirizing men’s base instincts. Based on actual events, War Dogs is a more sober comedy, meant to trigger our outrage, but it’s not quite smart or sharp enough to provoke the complicated wave of emotions it’s targeting.

The film stars Miles Teller as David, a twenty-something living in Miami in 2005 with his beautiful girlfriend Iz (Ana de Armas). As he explains in a self-consciously blasé voiceover, David works as a massage therapist for rich clients, dreaming of a better life for Iz and the baby that’s on the way, when he reunites with Efraim (Jonah Hill), a childhood friend back in town. Efraim is wealthy for reasons that seem shady, but soon he convinces his old school chum to partner on a lucrative new venture: Bidding on U.S. military contracts to assist with the ongoing Iraq occupation.

A movie like War Dogs makes a pretty strong case that, outside of perhaps Pulp Fiction, no film from the last thirty years has been as influential—or just straight-up copied— as Goodfellas. From its detached voiceover, to its you-are-there immersion into criminal behavior, to its pulsating soundtrack, War Dogs is but the latest movie to follow Martin Scorsese’s gangster blueprint.

But what separates Phillips’ film from many of its fellow imitators—at least for a while—is its poker-faced depiction of how easy it was for dweebs like David and Efraim to profit from the American government’s endless need for more weapons and vehicles. Focusing on smaller, insignificant orders that their well-heeled competitors wouldn’t bother with, these two guys fatten their bank accounts feasting on military crumbs.

Even if we can sense the film’s inevitable rags-to-riches-to-humiliation narrative kicking into gear, War Dogs keeps us distracted thanks to its dramatically fertile milieu. Phillips cleverly harnesses his previous films’ over-the-top macho comedic style and applies it to David and Efraim’s perfectly legal enterprise. Neither character is an outright bastard—at worst, David is easily persuadable while Efraim is an insecure hothead—and the fact that both men actually oppose the war only makes their behavior more despicable. As Efraim justifies it, it’s not like they can stop the war—so why not make a few bucks off it?

Among mainstream comedy filmmakers, Phillips is easily the most technically assured, giving his scenes a widescreen grandeur with a dynamic color palette and striking framing. This may seem to be an unimportant quality, but working with his longtime cinematographer Lawrence Sher, Phillips provides War Dogs with a visual sophistication that’s meant to complement what he considers a nuanced satire. On one level, the film highlights a perversion of the American entrepreneurial spirit, showing how two nobodies pulled themselves up by their bootstraps to help kill people halfway across the globe. (To make this irony more obvious, David and Efraim worship Al Pacino’s Scarface, a cinematic touchstone for how the pursuit of the American Dream can turn rotten.) Mixing action with comedy, thriller elements with intimate drama, War Dogs works on a large, bold canvas, and Phillips crafts a film as big as its characters’ monetary aspirations.

The problem is that, no matter how pretty War Dogs looks, Phillips can’t sustain his film’s thematic edginess. Once he and his cowriters establish the particulars of the gun-running world—the globetrotting danger, colorful characters, and exotic anecdotes—the movie becomes less an indictment of greedy profiteers or the Iraq War’s moral calamity than it is a rather rote detailing of how David and Efraim eventually met their downfall.

Teller is saddled with the straight-man role—the sweet guy perfectly willing to overlook his work’s ethical quandaries—and he brings his usual soulful intensity to the character. But it’s Hill’s movie. The actor has been in a Scorsese film, The Wolf of Wall Street, and here he plays a similarly slippery individual. Beefy with slicked-back hair, Efraim has a gregarious, ingratiating demeanor that makes you instantly distrust anything he says, but Hill is so boisterous and charming that we understand why the going-nowhere David convinces himself that their bond is real. Efraim never explodes into a violent rage because he’s a far more stealthy assassin: A master chameleon, he’s able to make himself into whatever the person he’s talking to wants to believe he is. Hill exudes a con man’s swagger, and much of the fun of War Dogs is wondering when he’ll reveal his true colors to his supposed best friend.

That moment will come, of course, and eventually so do other predictable plot points. War Dogs’ familiarity alone isn’t a deal-breaker, but Phillips’ belief that he’s making daring commentary is. With every obvious “ironic” song selection—Creedence Clearwater Revival’s “Fortunate Son” during a scene of the American military in action, Leonard Cohen’s world-weary “Everybody Knows” timed to the movie’s ambiguous final scene—Phillips betrays his shallow thinking about the material. The movie encourages us to revel in the bad-boy energy of its main characters—Hangover veteran Bradley Cooper plays a sleazy confidant, oozing malicious undertones—but its political observations never sting or knock us off-guard.

Part of the trouble is that War Dogs isn’t all that funny, presumably because Phillips assumes we’ll recoil in horror over what these ugly American exploiters are willing to do in the name of a dollar. But the bigger issue is that, despite this being a true story, Phillips sands the movie’s rough edges down so that it adheres to a comfortable, derivative crime narrative. War Dogs starts off longing to shock us with its incredible tale—it ends up presenting its story so generically that it loses the quirky irregularities of real life. We can’t be outraged because we’re never really challenged.

Grade: C+

Grierson & Leitch write about the movies regularly for the New Republic and host a podcast on film. Follow them on Twitter @griersonleitch or visit their site