The chief problem with The Dilemma, directed by Ron Howard, is that it's a comedy built upon an inherently false premise, and in its heart of hearts it knows this, so it expends all sorts of energy trying to fan smoke and throw sand in the eyes of viewers, obscuring this fact for the sake of "zaniness."
The story centers around Ronny Valentine (Vince Vaughn) and his pal and business partner Nick Brannen (Kevin James), who since college have been best friends. Working up a design for an electric vehicle that retains the bowel-shaking engine throttle noises of an old-school muscle car, the guys are close to landing an important sponsorship and funding deal that would help launch their company into the stratosphere and nail down secure futures for Nick and his wife, Geneva (Winona Ryder), as well as Ronny and his girlfriend, Beth (Jennifer Connelly).
It's during this stress-filled time, however, that Ronny's world is turned upside down when he inadvertently sees Geneva making out with another man, Zip (Channing Tatum), and makes it his mission to get answers. Launching into a rather hapless amateur investigation, Ronny learns that Nick has a few secrets of his own. He also separately confronts Geneva and her lover, but all his strange behavior arouses suspicions in Beth, and others, that Ronny, an inveterate gambler, has lapsed back into his addiction.
Howard trades mostly in a curiously flattened affect, and for the most part the film's comedy is rather listless, except when Queen Latifah shows up, as an auto business middle-management type, and keeps trying to awkwardly inject some forceful personality into the proceedings. The screenplay, by Allan Loeb (Things We Lost in the Fire) consistently and wearyingly contorts itself to avoid and forestall the reality of "guy code" — that any male worthy of being considered a real and true friend wouldn't fret over telling his best pal if he saw his friend's woman stepping out on him. It does this by having Ronny at first rationalize that it's not a good time, since Nick is very stressed, and then wade into a strange game of blackmail, wherein Geneva insists she'll reveal a shared secret from their past if Ronny deigns to break the news to her husband. All this is bullshit, quite frankly, and meandering, not very engaging or funny bullshit at that.
Vaughn invests his characteristic full-bodied energy into the proceedings, and through sheer force of will makes some moments not so painful; he's a natural laugh machine. But The Dilemma is much more interesting when it's a bit darker, and skeevy. The idea of Ronny giving a wildly inappropriate celebratory toast at Beth's parents' 40th wedding anniversary — as a not-so-veiled threat to Geneva to come clean — is gripping in a certain twisted way, but the film is so invested in more conventionally oriented "hijinks" that it misses its true calling: as a pitch-black comedy that doesn't pander for mainstream laughs. (Universal, PG-13, 112 minutes)