Four summers ago, The Break-Up surprised many viewers by following through on its title, forsaking the conventions of a breezy rom-com to detail the agonizing process of dissolving a relationship. Now its star, Vince Vaughn, returns with The Dilemma, another Chicago-based comedy that lurches into straight-up psychodrama, and the tonal instability keeps things lively even when the film seems intent on self-sabotage. Perhaps the shakiness comes from Vaughn, a reckless improviser whose monologues can wend from sour and sarcastic to grudgingly heartfelt and pitiable; he’s a man-child whose juvenile behavior can sometimes mask real vulnerability. It’s rare for a director as reliably down-the-middle as Ron Howard to let his movies go too far out on a limb, but The Dilemma is a wild ride, thrilling when it isn’t a calamity.
Vaughn and Kevin James star as best friends and partners in an automobile-development outfit who win a bid from Dodge to produce a muscle-car engine for a hybrid vehicle. When Vaughn discovers that James’ wife of 20 years (Winona Ryder) is having an affair with a younger man (Channing Tatum), he finds himself in, well, a dilemma: Does he tell his friend, whose ulcer is already bleeding from job pressure, or trust that Ryder will do the right thing and break the news herself? The longer he stalls, the deeper a mess he makes of it, endangering not only his friendship and career aspirations, but also his relationship to his own girlfriend (Jennifer Connelly), who’s flummoxed by his erratic behavior.
The Dilemma asks some compelling questions about what goes into a longstanding marriage and whether there’s some value in people keeping secrets from each other—so compelling, in fact, that it’s strangely jarring whenever it goes for laughs. The dynamic works out best for James, who’s more down-to-earth than Vaughn and more committed to playing a real character, but Vaughn’s performance has an erratic, train-wreck fascination that dominates the film. Whenever The Dilemma dips into melodrama for too long, Howard suddenly shocks it back to comic life like a defibrillator, with several scenes where the characters resort to fisticuffs, and an epic anniversary toast that toes the line between funny and mortifying. It never coheres as well as it should, but the film makes a fine mess.