The Extra Man

The Extra Man is a novel by Jonathan Ames and a movie directed by Shari Springer Berman and Robert Pulcini. It tells the story of Louis Ives, who left a teaching position in New Jersey under a cloud and came to New York to find himself. He gets a room in the apartment of an eccentric failed playwright named Henry Harrison, the titular "extra man", who spends his free time escorting (read: mooching off) wealthy widows at tony social events.

The book is set at the end of The Eighties; the film, released in 2010, is set in a vague contemporary New York with 1980s aspects.

Tropes:

 * Author Avatar: Louis Ives
 * Bondage Is Bad: Henry thinks so, at least. It's why he kicked his last roommate out of the apartment
 * Born in the Wrong Decade: Henry belongs in the 1920s or so, and Louis somewhat does too.
 * Catch Phrase: "Well, here we are. Where are we?"
 * Cloudcuckoolander: Henry; everyone, kinda
 * Creator Cameo: Author Jonathan Ames is a patron at Sally's in the film of his book.
 * Granola Girl: Mary, in the movie
 * Insistent Terminology: Henry is not a gigolo
 * Large Ham: Kevin Kline climbs the heights occasionally in the film.
 * Larynx Dissonance: John C. Reilly's high-pitched Gershon.
 * Meaningful Name: Henry and Louis display courtly manners and are involved in palace intrigue.
 * Painting the Fourth Wall: As the camera irises in on Louis on the brownstone stoop, he stumbles as if hit by the edge.
 * Wholesome Crossdresser: Louis is a heterosexual one, for certain values of "wholesome".
 * Wild Hair (and beard): Gershon