As the title suggests, the whole movie is built around a Catch-22 scenario. Suppose you have a best friend, with whom you have a sort of bromance thing going on. He's happily married to this beautiful gal, but you discover that she's cheating on him. The dilemma here is, do you tell him, or not ? To make matters worse, suppose you are both working on this big project and you're afraid that telling him will crush his focus and you'll end up losing a big contract. What do you do ?
"Shoot the hostage" would be the choice answer if this were "Speed", but it's not. The two best friends are Ronny (Vince Vaughn) and Nick (Kevin James). Ronny's not married, but is seriously considering tying the knot with Beth (Jennifer Connelly). He just can't find the right moment to propose, or perhaps he's stalling. The situation only worsenes when he witnesses Nick's wife Geneva (Winona Ryder) smooching with a tattooed guy (Channing Tatum). Ronny and Nick are working hard at building a daring new car prototype, or, at least Nick is. Ronny's too busy with his dilemma. He's trying to fix all the wrongs, while creating more wrongs in the process, which is why this is meant to be a comedy, I suppose.
Many have accused director Ron Howard that he shows no directorial vision in his movies and that his work is usually just cookie-cutter stuff, and I've often defended his movies against such criticism, but "The Dilemma" really does suffer from that exact kind of bland direction and writing. Any number of directors could have taken Howard's place and provided the exact same output. The moral dilemma at the core of this story is an interesting premise, but the filmmakers spend too much time trying to build comic set-pieces for Vaughn and not enough time making us care about these characters. There are even moments when the movie's flow just stalls, descending into boring and predictable cliches, while Vaughn's tireless rants try to tackle our attention span. It's hard to believe they couldn't squeeze more laughs out of this material. All the ideas seemed to be there, but they just couldn't make them work. The finished product is a seriously flawed comedy with big names on the credits.