Louis Ives (Dano), who really would like to be a character in an F. Scott Fitzgerald novel, is forced to leave his teaching job at a Princeton preparatory school. Off to New York he goes, and in seeking a place to stay, he looks at the prospect of a room in the apartment of Henry Harrison, who claims he’s a playwright and had his key work stolen from him. As played by the ever-marvelous Kevin Kline, Henry is a judgmental, arrogant oddball, who has no money but courts rich women who can give him a measure of social status, including being invited for the season in Florida. He is also extremely funny with his frowning upon sex of any sort, disdain for women, old-fashioned ideas and his weird mannerisms.

Louis, who takes the room despite is lack of privacy and comfort, is very impressionable and also vulnerable. He has landed a job in an environmental magazine and he would like to date Mary, a co-worker, nicely played by Katie Holmes. But he hasn’t a chance with her. There is only a smidgen of plot to the film. Most of the enjoyment comes from watching the relationship between Louis and Henry, who has become something of a mentor. Among the monumental lessons Louis absorbs is how to urinate in the street without anyone noticing.

Louis, trying to find out who he really is, explores his urge to cross-dress. There is a droll scene in which he hires a specialist to make him look like a woman. But made-up, he stares into a mirror and is aghast. Cross-dressing isn’t all it is cracked up to be. “The Extra Man” is often witty, and even while we are laughing at Henry's arrogant behavior, Kline manages to give him a likable side. Dano also succeeds in making Louis appealing for his shy, decent manner.

The film has some excellent character work. Marian Seldes is a gem playing the rich old lady Louis is sent to accompany to dinner as a substitute for Henry. Seldes projects the inner sadness of having aged to the point of infirmity yet hinting at a sparkle that was once there. John C. Reilly plays Henry’s eccentric neighbor, with a high-pitched voice that makes him sound like a castrati when he talks, but deepens when he sings.