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Upon its release in January 2011, The Dilemma was poorly received by critics and audiences alike. There is still and has always been confusion surrounding it, with every withering review asking the same thing: “What kind of movie is this supposed to be?” It’s far too serious to be a comedy and too outrageous to be a drama. It’s too extravagant for a satire and too sharp for a mindless college flick. The jokes are extremely crude, yet wildly intelligent. It is, by all accounts, a complete mess. However, I would argue that while the film is disorganized, it isn’t a mess.
Reveling in the Dilemma is made easier for those with an appreciation for platonic male love, scenic views of Chicago, and Ron Howard’s stunningly subtle artistry. Even still, fully accepting the Dilemma mandates tolerance for tonal incongruity, along with a sociological curiosity regarding the juxtaposition of the earnestness of the bromance, and the dominance of toxic masculinity.
Vaughn plays Ronny and Kevin James portrays Nick, Ronny’s best friend and business associate. They own a small automotive design company that is about to seal a deal with Dodge. Nick and Ronny have beautiful partners played by Jennifer Connelly and Winona Ryder. Things start to go awry when Ronny catches Geneva [Ryder] in bed with a young stud (Channing Tatum, in a wonderfully strange performance).
Now for the titular dilemma: should Ronny spill the beans to Nick? Complicating matters further, Nick seems to be scrambling to finish his outline for a significant meeting with Dodge. If Ronny decides to inform Nick, would it be best to wait until after the meeting from a business perspective? Funny, right? Indeed and not at the same time. You can make sense of this dichotomy if you want, and that’s the reason so many people dislike the film.
From the beginning, with the opening credits, Howard is quick to let us know that this won’t be a run-of-the-mill studio comedy film. The scene cuts to our four main characters in a buzzing restaurant and Howard moves from beautiful closeups to sharp black-and-white credits. The dialogue is chaotic as it flip flips in between mundane conversation, deep thinking, and witty comebacks. It looks like a loose combination of John Cassavetes, Woody Allen, and Judd Apatow, an alchemy at play for the entire movie which creates a simultaneously unsettling and captivating feeling.
In one way, The Dilemma is far more tolerable than you’d think. A decade afterward, the stereotyping dialogue sounds less like casual racism and more like a covert critique of the white male privilege (which is basically what Howard was defending when there was a fire about a line in the film where electric cars were described as “gay”). In an easier movie, The male protagonists would be over idolized and the blunter aspects of the film would be sandpapered down. But Nick is not all good, and Ronny’s journey is hardly all good. An easier movie would also have a subtler treatment of this crucial moment where Ronny and Nick address each other from a group and use the words that are hardly ever heard from men’s (both on screen and off) mouths – sincerity. Rather than serve it in a tongue-in-cheek, the movie takes the bold approach of staying with its characters as they share the kind of vulnerability that is usually reserved for women.
However, instead of focusing on easy-going and entertaining bromances, The Dilemma tackles the issue of how a camaraderie can spiral out of control into a “bros before hoes” attitude, characteristic of toxic masculinity. The film’s ending at the United Center is both exhilarating and disturbing. While Ronny and Nick indulge in pure male fantasy, the women are either missing or relegated to the periphery. As far as Ronny and Beth’s (Connelly) romance goes, it is simultaneously impossibly romantic and tragically realistic. Ultimately, he wins the girl, the job, and a ‘guy’s getaway,’ while his fiancée is simply lucky to be married to him.
Even as I try to keep my focus, I find the pacing exhausting. The moments where Ronny’s anniversary toast and the Chicago botanical garden scene take pause would greatly test the patience of viewers who find elements of both situations to be unbearably cringeworthy and over-the-top slapstick. There are almost certainly parts of the film people would have preferred to be left on the cutting room floor, but that’s what makes it so impactful: the movie refuses to bend to societal expectations. The Dilemma’s lack of polish allows the film to tackle the troubling essence of male friendships without losing the lightheartedness that accompanies them. This unique blend is what allows The Dilemma to present its harsh truths mixed in with hilarious moments – and is what makes it so iconic.
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