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Hear me out: why The Dilemma isn't a bad movie

Stephen Snart
·4 min read

When The Dilemma opened in January 2011 it was met with critical contempt and box office apathy. Audiences then and now are befuddled by it and every scathing review asks the same question: “What kind of movie is this supposed to be?” It’s too serious for a comedy but too silly for a drama. It’s too bro-tastic for a satire but too incisive for a mindless frat pack foray. It has very insightful jokes and very crass jokes. By all accounts, it’s a mess. But I argue, that while the film is messy, it’s not a mess.

Related: Hear me out: why S1m0ne isn't a bad movie

Enjoying The Dilemma is made easier with a pre-existing appreciation for three things: sincere displays of platonic male love, postcard-perfect pictures of Chicago and Ron Howard’s quietly impressive craftsmanship. But even then, to fully embrace The Dilemma also requires a tolerance for tonal discordance and a sociological interest in the bridge between the earnestness of the bromance and the gender hegemony of toxic masculinity.

Vaughn stars as Ronny and Kevin James plays Nick, his best friend and business partner. They run a small automotive design firm that’s on the verge of a long-term contract with Dodge. Ronny and Nick both have stunning significant others played by Jennifer Connelly and Winona Ryder. Everything is looking up until Ronny sees Geneva (Ryder) cheating on Nick with a young hunk (Channing Tatum in a hilarious, off-kilter performance).

Enter the titular dilemma: should Ronny tell Nick what he saw? Enter a complication: Nick is under pressure to produce his concept for a big meeting with Dodge. If Ronny is to tell Nick at all, should he wait until after the meeting for the sake of their business? Funny, right? Well, yes and no. And that’s why so many viewers are turned off by the film.

Right from the opening credits, Howard signals this isn’t a generic studio comedy. As we see our four leads engaged in lively conversation at a trendy restaurant, Howard intercuts between gorgeous close-ups and stark black-and-white credits. The dialogue proves similarly disorienting as it rapidly switches between small talk, philosophical inquiry and one-liners. It feels like an unstable blend of John Cassavetes, Woody Allen and Judd Apatow, an alchemy that bubbles throughout the entire movie, making for a simultaneously off-putting and stimulating experience.

In a way, The Dilemma has aged better than you’d expect. Ten years later, stereotyping dialogue seems less like casual racism and more like stealthy commentary on privileged white males (which was essentially Howard’s defense when a line in the film about electric cars being “gay” rightfully drew controversy). In an easier film, the male leads would be glorified and the film’s sharp edges sanded down. But Nick is neither infallible nor pure and Ronny’s quest is not strictly virtuous. And an easier film would be less sincere in a pivotal scene where Ronny and Nick speak to each other – in front of a group – with the kind of earnestness so rarely spoken between men (in film or in real life). Instead of playing it tongue-in-cheek, the film bravely hangs with its characters as they share the kind of vulnerability normally coded as weak.

But what The Dilemma does differently from the more genial and successful bromances is acknowledge how male friendship can devolve into the type of “bros before hoes” mentality associated with toxic masculinity. The film’s conclusion at the United Center is both rousing and unsettling. Ronny and Nick experience unadulterated male wish fulfillment while the female characters are either absent or left on the sidelines. Throughout, Ronny’s relationship with Beth (Connelly) feels both far-fetched and sadly true to life. In the end, he gets the girl, gets the job and gets a bros trip while his fiancee simply gets the good fortune of being engaged to him.

And yet, I admit the amount of time spent squirming because something’s too serious or not serious enough makes for an exhausting watch. I can’t fault anyone who finds Ronny’s anniversary toast unbearably cringe-inducing or the Chicago botanical garden scene to be ludicrously slapstick. In the end, there may be scenes you wish played out differently or jokes you wish were cut, but there lies the film’s strength: it’s deliberately not the movie anyone wants it to be. By being messy and free from conformity, The Dilemma can explore the insidious undercurrents of the bromances without sacrificing the infectious joviality of male bonding. That peculiar balance is what enables The Dilemma to get at some hard truths and some hard laughs. And that’s what makes it worth watching.

  • The Dilemma is available to rent digitally in the US and UK