Straddling the line between industry and art (and doing neither that well), “Two Lovers,” James Gray’s latest film about wayward souls in Brooklyn, gives an unexpected ladies’ man a set of choices. Good girl versus crazy girl. Cute Jewish girl versus pill-popping ADHD club chick. Business partner’s daughter (will buy you leather gloves) versus hot neighbor (miscarriage-prone). Sex in his parents’ apartment after 90 seconds of small talk versus sex against a brick wall outdoors in November. Vinessa Shaw versus Gwyneth Paltrow. If only all of us were faced with such difficult decisions.

Leonard Kraditor (a mumbling, grumbling Joaquin Phoenix, who apparently walked right off the set and onto “Late Night”) starts off as a mopey loser living at home after a breakup with his fiancée. Presumably, he has bipolar disorder, but his ups and downs seem decidedly normal for someone who has two beautiful women suddenly walk into his life and, at night, goes home to boringly stereotypical old-world Jewish parents, Reuben (Moni Moshonov) and Ruth (Isabella Rossellini).

Gray’s typical Brighton Beach setting—2007’s “We Own the Night” and his 1994 debut “Little Odessa” were set there—seems bleaker than ever, a halfway house for Manhattan mistresses like Michelle (Paltrow, in a truly fearless performance) while still grudgingly remaining a home for daughters of Jewish businessmen. Sandra Cohen (Shaw, sporting the latest from the Jennifer Garner line of cheekbone implants)—the daughter of one of Brooklyn’s famed dry cleaning éminence grises—relentlessly hits on Leonard while he pursues Michelle. “I love you,” he tells Michelle, with a stare that could turn Glenn Close to stone. “I didn’t think I’d ever love anyone again. But I do. I love you.”

Like “We Own the Night,” “Two Lovers” sees Phoenix moping around Brighton Beach, spouting bad lines. Similarly, there’s also some very inventive sound editing; in the opening scene, where Leonard throws himself into Sheepshead Bay, the ambient noise fades out and we’re surrounded by dull, claustrophobic thumps, richly evocative of Leonard’s mental walls as well as the physical ones of his parents’ apartment. (Gray pulls the same trick during a rain-soaked car chase scene in “We Own the Night.”)

Unlike his marginally superior previous effort, which made no bones about being a police thriller, “Two Lovers” suffers from a general languor borne of Leonard’s lack of purpose and lack of definition. He has a mild speech impediment (which sounds exactly like Phoenix’s inebriated Johnny Cash), yet can pull out dance moves no white man has possessed since the late 70s. He effortlessly seduces two beautiful women, but is gawky around his parents’ friends (especially Sandra’s father, a cookie-cutter Jewish stereotype). He’s bipolar, but rarely shows any emotion, be it depression, elation, or anything in between.

Gray uses Leonard’s bipolarity and Michelle’s ADHD as an excuse to write bad dialogue (Leonard to Michelle: “He left you. I’d never do that. I’d take care of you. Because that’s what you deserve. You deserve to be loved”). He has no excuse for Sandra, though, who professes to Leonard over chocolate pudding, “I want to take care of you. I feel like I understand you. You’re different. You don’t pretend to be something you’re not. You don’t have to worry about anything. Don’t have to be embarrassed.” And then Leonard responds (I am not making this up): “You know, I’ve got a lot of stuff going on right now. I don’t even know what it’s like to be myself right now.”

Ditto, Lenny. He’s a dirtbag for leading both Sandra and Michelle on like he does while expecting us to sympathize when he broods like some character out of an artsy feel-bad movie (Darren Aronofsky’s “Requiem for a Dream” and “The Fountain” being the prime offenders). The “Match Point”-esque ending is designed to be a carnival of conflicted pathos—Woody Allen’s romantic anxieties shot through with Martin Scorsese’s manly poetics—but Gray’s attempt to be an auteur of enclosed spaces and private struggles is mired by bad scriptwriting filled with well-worn tropes of romantic drama. He should embrace his Hollywood side, and it actually looks like he might: his next project is a Paramount thriller starring Brad Pitt called “The Lost City of Z.”

—Staff writer Kyle L.K. McAuley can be reached at kmcauley@fas.harvard.edu.