A sophisticated and moving comedy, THE EXTRA MAN follows Louis Ives (Paul Dano), a lonely dreamer who fancies himself the hero of an F. Scott Fitzgerald novel... When a deeply embarrassing incident forces him to leave his job at an exclusive Princeton prep school, Louis heads to New York City to make a fresh start. He quickly finds a nine-to-five job at an environmental magazine, where he encounters an entrancing, green-obsessed co-worker Mary (Katie Holmes). But it's Louis' new home life that really sparks his imagination. He rents a room in the ramshackle apartment of Henry Harrison (Kevin Kline), a penniless, wildly eccentric but brilliant playwright. When Henry's not dancing alone to obscure music or singing operettas, he's performing - with great panache - the duties of an "extra man", a social escort for the wealthy widows of Manhattan high society. These two men, separated in age by more than forty years, develop a volatile mentor/apprentice relationship. Through a series of urban adventures where they encounter everything from a leaping lion to a wildly jealous hirsute neighbor, from drunken nonagenarians to a shady Swiss hunchback, Louis and Henry form a memorable bond that bridges their differences.