When Nice Becomes Vice: The Hardening of Chris Messina

“When I was doing Vicky Cristina Barcelona,” said Chris Messina, “and Rebecca Hall was, like, giving me the side of her lips to kiss, because she wasn’t into me, you go home with that, you go home feeling unwanted.”

Mr. Messina is a nice guy known for playing “nice guys,” with all that the phrase implies-shiny congeniality, a blandly accommodating personality, unthreatening smirks. His characters in Six Feet Under (supportive, conservative boyfriend), Vicky Cristina Barcelona (supportive, dull fiancé), Julie & Julia (supportive, hungry husband) and Away We Go (supportive, secretly sad husband) weren’t all the same man, but they could all have been in the same frat together, about a decade ago.

Mr. Messina wants to blow that image up, or at least nudge it off track, with his new film, Monogamy (to be released March 11 by Oscilloscope Pictures), the feature-filmmaking debut of Murderball documentarian Dana Adam Shapiro. His character, engaged to an appealing Rashida Jones, becomes obsessed with a woman he’s paid to follow and photograph. For long portions of the film, Ms. Jones’ character is in the hospital, and Mr. Messina’s character, on a frolic of his own, neglects her.

His character in Julie & Julia, on the other hand, indulges his girlfriend’s French-chef fantasies for far longer than any audience member was willing to. He was in the film to make Amy Adams look winning because she was dating a nice guy. His characters tend to be overshadowed by women with more intriguing struggles. There are no small roles, though, as the saying goes, and Mr. Messina has refused to be a small actor, inhabiting the boyfriend-of persona with a barely visible effort.

So will Mr. Messina always be stuck playing boyfriend parts?

“It’s funny. I come from New York theater and did a bunch of really interesting, complicated characters here. When I went to Los Angeles, I got Six Feet Under, and I played a Republican lawyer who marries Lauren Ambrose’s character. And everybody in New York was like, ‘Oh, that’s such a crazy character for you, because you’ve played these drug addicts and gang leaders.’ And it was kind of a blessing and a curse.” Six Feet Under, in which Mr. Messina stabilizes Ms. Ambrose’s manic-artist character, begot Vicky Cristina Barcelona; Mr. Messina says he was cast in Woody Allen’s Catalan romp because of the TV show. Interviewers began asking, “Are you really that nice?” It was time for a change.

A drug dealer or a gang member Mr. Messina is not in Monogamy, but he’s also not the epitome of a supportive husband. Indeed, the entire movie is about his attempts to avoid the sort of fate that some of the actor’s other characters have reveled in-subordinate codependence. “This kind of, for me, was the first step away from those nice-guy roles. Because I am a nice guy, I can be an O.K. guy, but I’m also a complicated guy, like everybody else,” said Mr. Messina.

The complications of Mr. Messina’s Theo drive the entire movie: He and Ms. Jones’ Nat have a functional relationship that Theo torpedoes out of boredom or lust or angst. The role is somewhat underplayed-there’s no moment of bellowing à la Ryan Gosling in Blue Valentine. But not every movie needs a Stanley Kowalski. Mr. Messina and Ms. Jones (who, perhaps uncoincidentally, has played a nice girl in The Office and Parks and Recreation on television) drift apart slowly, and convincingly. 

“I love the chameleon aspect of it,” Mr. Messina said of playing a character removed from what has been his wheelhouse. If Theo is defined by his relationship, he’s also the far more erratic and dramatically complex character, whose seeming sleepy enthusiasm masks chasms of discontent. Mr. Messina considers Gary Oldman a paragon of this chameleonic style of acting. While Mr. Messina may still, at 36, be too good-looking for what he terms “the long marathon of a character actor’s career” (character actors tend to look more like, well, Mr. Oldman) or too unambiguously nice and unthreatening to pull off an Oldmanian disappearance into a role, the tests are beginning in earnest. One of his next roles is as a street performer in silver body paint who falls in love-an eccentric turn and a chance to prove his range.

But Mr. Messina’s best moments in Monogamy-among them a tough conversation with Ms. Jones and wordless moments of contemplation in which Mr. Messina’s chemistry with actresses isn’t available to him-resemble the acting of Mark Ruffalo. Mr. Ruffalo is an actor who can play only a limited array of roles: His career has been a gallery of impossible-to-pin-down aging free spirits. But within that framework he can evoke unexpected emotions, and new combinations of emotions with each film. That Theo starts the film as a basically uxorious boyfriend (and diverges, afterward, from that) sets the film within the Nice-Guy Chris Messina canon; the variations here are intra-Nice Guy. Mr. Messina didn’t have to learn an accent or train for years to prove his range for this movie, but he proved his range anyhow.

But there are other actors out there to idolize. Mr. Messina, who named one of his two children after Montgomery Clift, can scarcely believe that he worked with Javier Bardem on Vicky Cristina Barcelona. (The pair shared but a scene.) When he saw Mr. Bardem at the junket for the film, Mr. Messina said, “my hair was longer and I had facial hair, and I was like, ‘We gonna get fucked up tonight?’ This was the premiere. And I was like, ‘We gotta get fucked up tonight! We’re gonna get drunk tonight, right?’ And he was looking at me like I had 10 heads, and it was because I wanted him to know, ‘I’m not that guy! I’m not that guy!'”-i.e., the cuckolded boyfriend of the film.

Mr. Messina has been researching post-traumatic stress syndrome in soldiers for an arc as a veteran on the next season of Damages, which is currently shooting. He grew a beard for the role, and is wearing a red-and-black flannel shirt; although he’s sitting in a posh-ish Manhattan hotel, he looks as though he’s back in Brooklyn, where he shot Monogamy in just 18 days and shot Damages yesterday. It’s a far cry from the preppy look he wore in Vicky Cristina Barcelona or Six Feet Under: He looks like his Monogamy character, or himself. “I’d love to move my whole family out here,” he said. He got the role in Damages based on scenes from Monogamy, in a nice reversal of his last big television role, one that made him famous in just one way.

ddaddario@observer.com When Nice Becomes Vice: The Hardening of Chris Messina