katie holmes
Louis Ives (Dano) fancies himself a hero in an F. Scott Fitzgerald novel. He favors neckties, blue blazers, and sport coats.
After an embarrassing incident involving a brassiere fetish, he loses his teaching job at a Princeton prep school and heads to New York to fulfill his dream of becoming a writer.
In New York, he rents a room in the madly discombobulated apartment of Henry Harrison (Kline), a failed but brilliant playwright who dances alone to old Broadway records, sneaks into the opera, and performs, with great style, the duties of an "extra man" -- an escort for the rich widows of the Upper East Side.
While Louis dreams of escorting dowagers himself one day, he becomes infatuated with Mary (Holmes), a socially-aware co-worker at the environmental magazine where he is employed and befriends Gershon (Reilly), Henry's hirsute musical neighbor.
The two men (Kline and Dano), separated in age by more than forty years, eventually develop an irascibl mentor/apprentice relationship, and they form a bond the depths of which is hardly expected.
Starring: Kevin Kline, Paul Dano, Katie Holmes, John C. Reilly