Into the dismal arena of January, when nearly all films strain to appeal to the broadest and dumbest audiences, enters The Dilemma, an odd bird trying so hard to straddle genres and tones that it strains itself mightily. The Dilemma isn't exactly a good movie, nor is it weird or disastrous enough to be some kind of midwinter indoor sideshow, but it's fairly interesting to observe as it tries to balance farce and brutal honesty in ways that nearly always fail. Sporting glimmers of hope here and there-- a funny supporting turn from Channing Tatum, a few jokes or insights that stick-- The Dilemma once in a while shapes into the movie it wanted to be, making it all the more baffling when it falls right back on its face.
The premise of Allan Loeb's shoddy and rambling screenplay is textbook screwball comedy: Ronny (Vince Vaughn) and his business partner/best friend Nick (Kevin James) are on the verge of a huge business deal when Ronny sees Nick's wife Geneva (Winona Ryder) kissing another man. Telling Nick about it would send him off into a depression that would jeopardize the deal, so Ronny keeps his mouth shut, driving himself crazy in the process. He's supposed to be proposing to longtime saint of a girlfriend Beth (Jennifer Connelly) but instead digs deeper into Geneva and Nick's dysfunction, following her on a tryst with tattooed lover Zip (Tatum) and Nick on a visit to a "happy ending" massage parlor. The farce structure keeps everyone in the dark about each other until a contrived climax but there's plenty of suffering in the meantime, from Ronny's allergic run-in with exotic plants to a violent confrontation with the insecure and heavily armed Zip.
The wonderful thing about the movies is any of those scenarios could be played for laughs or for drama, and The Dilemma, with somewhat admirable ambition, goes for both every time. It works once in a while-- all of Tatum's scenes pop with humor and also barely disguised rage, and Vaughn sells Ronny's complete meltdown with surprising pathos but also fast-talking charm-- but leaves the audience unsure how to follow the movie from one scene to the next. It's not just that Loeb's screenplay doesn't establish compelling characters or a believable comedic world that they live in, but that the plot veers from thread to thread in utter chaos, lending no sense of building action to the increasingly nutty proceedings. For a while we're meant to be concerned about Ronny's proposal to Beth, but then his old gambling addiction is dredged up halfway through, and by then Geneva's desire to keep her affair under wraps has turned her into a glowering psychopath not all that far removed from the character Ryder played in Black Swan. And with all that going on there's still an inordinate amount of time spent on Ronny and Nick's big business deal, where Queen Latifah is awkwardly enthusiastic and the boys get to drive some fancy cars, I guess to add some testosterone to a plot that's otherwise all about love and its consequences.
Howard directs all of this on apparent autopilot, tossing in sweeping shots of the Chicago skyline and strange extreme close-ups to transition between scenes, allowing Vaughn and James to cut loose on their own comedic tangents, and ensuring that Connelly fills the frame with her beauty and zero interesting things to do or say. I'm not sure if he wasn't sure how to balance the film's efforts toward drama and comedy or just didn't try, but The Dilemma is likely to please no one, neither the comedy seekers drawn in by James and Vaughn's mugs on the poster or the more sophisticated grown-ups who hear the movie is darker than you expect. There's more going on here than it seems on the surface, yes, but not much that actually works.
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