Director and screenwriter Peter Bogdanovich has often looked to the past for inspiration; this time he revives the screwball comedy genre he enjoyed success with in the early 70s.
There's a Woody Allen feel to She's Funny That Way, an ensemble piece centred around a New York prostitute turned actor who retells to a cynical journalist (Illeana Douglas) how she was "discovered".
Imogen Poots holds down the central role of Izzy, a real-life hooker who auditions for the role of a hooker in a Broadway play, and discovers the director is a recent client who gave her a large sum of money so she could follow her dreams.
Izzy's involvement throws the production into chaos. Director Arnold Albertson (Owen Wilson) has already cast his wife Delta (Kathryn Hahn) and her old flame Seth (Rhys Ifans), who's become aware of Arnold's adulteries. And lovely young playwright Joshua (Will Forte) immediately falls for Izzy, despite dating unbalanced psychiatrist Jane (played by Jennifer Aniston in Horrible Bosses mode). To top it off, Izzy is also being stalked by a private investigator on behalf of an infatuated elderly judge.
It's a lighthearted, somewhat amusing romp written by Bogdanovich and his ex-wife Louise Stratten, filled with interweaving stories that twist and turn, and are amplified when it becomes clear this isn't the first time Arnold has "mentored" a prostitute.