The title "The Dilemma" carries an air of mystery and conflict, and doesn’t give away much more than that. That’s the way Ron Howard wants it. And as serious as the name indicates, the veteran director is tackling his characters’ quandaries with comedy.
 
Vince Vaughn and Kevin James star as Ronny and Nick, business partners, best friends and vessels of the uncertain, as the former contemplates marriage to his longtime girlfriend (played by Jennifer Connelly) and rethinks his perception of Nick’s own marriage (to Winona Ryder).
 
It starts with cheating, or what Ronny sees as cheating, when Ryder’s Geneva appears to be canoodling with somebody who is not her husband(Channing Tatum). Still sound like comedy?
 
“’War of the Roses’ was a pretty funny movie and pretty painful, you know? So if you get that kind of high-pressure adult situation right, I think you can have fun with it,” Howard said on set in Chicago. “Kevin is dead-honest in this, so is Vince. And yet it’s a heightened situation.   So they get to some pretty funny, pretty intense comedically intense places. It’s kind of a broadening of what you might expect them to do. The tones are, you know, a little broader. A little more dimension, you know, just a little more dimension… a sort of broader comedy.”
 
Howard promises twists and turns of secrets and unknown variables, all within the plot of the original script. But the laughs are churned out of the comedic prowess of Vaughn and James together, resulting in scenes being shot and reshot with their improvisations tweaked each time. The trailer to the film caused its own dilemma with its brand of comedy – more than Universal intended – but months before the dust-up, the comedians were honing each emotionally charged scene with comfortable ad-libbing and their own style.
 
During HitFix’s visit to the set, Howard was talking his actors through one of those kind of scenes, where the script was wide open for improvisation and playing around, despite the heaviness of the situation: Ronny desperately is trying to tell Nick something but can’t find the heart, and Nick has only a limited time before he has to make an important call for their car company. Meanwhile, Ronny’s face has a rash painted all across it, which Nick only notices midway into their conversation.

And the page opens up.

“It burns when I piss,” Vaughn sputters, and James flops sideways on the couch laughing. Let’s try it again.
 
They’re sitting in their characters’ business car garage, with performance vehicle literature and parts and plans plotted all around the warehouse. It’s the real deal, with a muscle car sniffing their characters’ direction all the while they’re trying to nail the scene after a couple dozen takes.
 
“When we were doing those kind of improvs and things like that you need to make sure you get plenty of coverage so you can pick and choose and build around the great nuggets and still get back to the script. And so it’s a big editing job ahead. But a fun one. Should be fun,” Howard continued.
 
Ryder and Connelly play it more straight, generally sweet Midwestern girls who support their boys’ auto start-up company. Connelly – who worked with Howard previously on “A Beautiful Mind” – says she admires her character’s easy-going spirit, the steady element as Vaughn’s world spins into chaos over his discovery.
 
“She's just one of those people that you go, 'God. I wish I reacted like that in that situation.' She's just kind of nice,” she says, noting that audiences may be surprised by how Vaughn turns out, as well. “Obviously it's funny and he's very funny in it, I think, and he and Kevin are really funny together. But also there are scenes that are moving and a little more dramatic and it was nice for me to see him doing that, too. You don't get to see much of that side of him.”
 
Audiences have seen broad comedy from Howard before, but the realism of these relationships is tamed by the gravity of Vaughn’s “dilemma” and even by the location itself. And It doesn’t hurt that Vaughn hails from the Windy City.
 
“Vince has been a great guide in that regard. We didn’t have the Black Hawks in the movie in the first draft or Weiner Circle or places like that. And now we have key scenes in those environments,” he said. “I loved [Chicago] 20 years ago doing ‘Backdraft,’ which used the city well in a very different way. We’re dealing with a very modern set of relatable relationship issues—emotional issues—but we’re doing in a Midwestern kind of bad-ass way. “