Tux Capacitor: Dano, left, and Kline draw from The Great Gatsby.

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A dismissed prep-school teacher moves to Manhattan to indulge in yearnings both writerly and otherwise in The Extra Man, an adaptation of Jonathan Ames’ novel whose literary flavoring eventually drowns in forced whimsy. Louis (Paul Dano) is a meek Fitzgerald lover who imagines himself as a Nick Carraway-like protagonist, complete with grandiloquent narration. He dresses in ’20s-style suits and strives to conduct himself as a “young gentleman.” Except, that is, when he’s feeling inexplicably drawn to ladies’ delicates, and wishes he could look in the mirror and see a pretty girl gazing back. It’s Louis’ unfortunately timed discovery of a student’s bra that gets him fired, and once he arrives in New York, his exploration of his cross-dressing impulses seems to overshadow his desire to write a Great American Novel.

Louis’ Gatsby is Henry Harrison (Kevin Kline), a gray-haired and dirt-poor playwright who takes Louis in as his boarder. Henry repeatedly insists that they shouldn’t get to know each other too well, but they still discuss literature (Henry James is “unreadable”), women (who shouldn’t be educated, according to Henry, nor fornicated with in his apartment), and cars (Louis’ sentimental backstory involving his Pontiac Grand Ville is met with, “Well. I drive a Buick!”). Sex is a particularly touchy subject for Henry, who’s lost friends and other roommates because of his extreme ideas about fetishes and perversion, though he himself is employed as an “extra man,” or a more genteel gigolo. His clients tend toward the rich and the elderly, to ensure both chastity and maximum perks.

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American Splendor collaborators Shari Springer Berman and Robert Pulcini co-directed and wrote The Extra Man, and its first half is a delight, steeped in lofty, dryly witty conversations and elevated by Kline’s charming eccentric, who would be the star professor of any English department. Henry speaks highly of the opera but has devised a method of sneaking in; he winters in Florida but only with the permission of one of his wealthy mistresses. Dano’s Louis is soft-spoken and gentle, and not quite irritating despite his neurotic blinking and wallflower dialogue choices. But he’s saved by the character’s intelligence and inherent spine, deeply buried though it may be. When Louis starts taking baby steps toward transvestism, it’s aching, because even in this world he feels uncomfortable and newly convinced that he’s unlovable.

But then the film flies one freak flag too many. Henry becomes a crotchety jerk who’s clearly out to use people, a theme that hammers the viewer until the end: Katie Holmes, for instance, has a superficial and largely useless role as Louis’ co-worker at an environmental magazine who’s only nice to him when she’s about to ask a favor. Henry gets upset at Louis but then invites him on a trip to the ‘burbs, but really he just needs a ride. And Henry’s estranged friend and neighbor, Gershon (John C. Reilly), whom Henry first describes to Louis as a pal “who helps carry things,” is exactly that, a mechanic who helps Henry with his car and whatever other chores he can’t handle alone.

Gershon is initially a priceless sight gag, with Reilly tressed and bearded like Harry Potter’s Hagrid and occasionally seen glaring at Louis after he moves into the building. When he finally makes amends with Henry, though, it’s a disappointment—Reilly affects a high pitch for seemingly no other reason than to set up a single joke. (Henry’s voice is affected, too, but it fits his more well-rounded, smarter-than-though character and sharpens lines like, “I need alcohol and civilization!” when he injures himself on a beach.) Louis’ inner turmoil, meanwhile, doesn’t go anywhere that’s especially interesting; the story opts instead for cheerier ties to its loose ends. For all the film’s emphasis on higher education in academia and the School of Life, no one seems to learn much.