Independent Film Festival Boston 2010

In this quirky comedy directed by Shari Springer Berman and Robert Pulcini (AMERICAN SPLENDOR) and based on the novel by Jonathan Ames (creator of the HBO series Bored to Death), Louis Ives (Paul Dano) leaves his job teaching high school English after an embarrassing situation prompts his departure. He aspires to start anew by becoming a writer in New York City.

Scouring the classifieds, Louis secures a room on the Upper East Side in the dilapidated apartment of an eccentric, long-struggling playwright, Henry Harrison (Kevin Kline, 2010 recipient of IFFBoston’s Career Achievement Award). Soon, Louis learns that Henry earns his keep by being an “extra man”—an escort to wealthy dowagers. Intrigued, he begins learning from Henry how to be one, too.

Louis and Henry develop a deep connection as they weave their way through a number of indelible, amusingly oddball, and distinctly urban encounters with characters played by an ensemble cast that includes John C. Reilly, Katie Holmes, and Patti D’Arbanville. Dano’s quiet, genuinely sweet-tempered performance is a perfect pairing with the élan with which Kline embodies Henry Harrison.

—Callista Burns