Peter Bogdanovich’s final feature is one of the more morose comedies ever made. Whether this is intentional or not remains to be debated. What is clear, however, is the strange mixture of ideas and genres that was so often Bogdanovich’s preference for comedy. He was enthralled with the idea of making old-fashioned screwball comedies set in and dealing with issues of the modern (or even post-modern) era. While What’s Up, Doc? came closest to achieving that unity of style and subject matter, She’s Funny That Way (originally titled Squirrels to the Nuts) is full of old-fashioned gags with new-fashioned actors and situations. The wit and elegance of the comedy stars of yesteryear is missing from this ragtag group of eager but often miscast actors.

At the center is Izzy (Imogen Poots, letting her New York accent slip periodically), a call girl who services a famous Broadway director (Owen Wilson) and is given enough money from him to never be a prostitute again. This strange comic premise stems from Bogdanovich’s experience in Singapore while shooting Saint Jack where he did the same thing with local women. However, the story would have more dramatic weight if it was set in a time and place when prostitution was dangerous enough that women would want to flee, which would certainly be truer of 1970s Singapore than 2010s New York City. Yet, because this is a screwball we must accept the rational arguments while the story is sent through the tried-and-true formula of coincidences and misunderstandings in order to elicit laughs out of material that does not ring as funny as it must have to its director.

More than most directors, Peter Bogdanovich’s personal and creative lives were inextricably intertwined. From working closely with his first wife, Polly Platt, on their earliest projects, to casting girlfriend Cybill Shepherd in multiple leading roles, to falling in love with Dorothy Stratten, there have been few instances where reality and the silver screen fantasy did not overlap for Bogdanovich. Indeed, She’s Funny That Way was co-written and produced by Louise Stratten, younger sister of Dorothy and Bogdanovich’s wife at the time the script was conceived. This, coupled with the fact that the movie’s premise was acted out by Bogdanovich in Singapore decades earlier, makes it more than conceivable that the ideas behind this movie are to some degree Bogdanovich’s own views on sex, relationships and family amidst a magical backdrop of New York City a la They All Laughed. Like that earlier movie, Bogdanovich thoroughly mixes comedy and tragedy, albeit tragedy lite. As the story goes, Wilson frees this hooker with a heart of gold from her chosen profession, only to run into her again when she auditions for his newest play next to his wife/star (Kathryn Hahn). Naturally, the wife has her own squeeze on the side and various other characters, including Jennifer Aniston as an annoyed therapist and Will Forte as her mild-mannered playwright boyfriend, contribute to the plot’s zany and goofy sensibility. To be sure, these actors, nearly all of whom must have jumped at the chance to work with Bogdanovich, do give their roles enough entertainment value, especially Aniston, who flies off the rails in nearly every scene she’s in and places the movie’s emotions properly in the realm of exasperation and irritation. Indeed, it is primarily the women who feel this way about their men (although Hahn is far less funny) as the men seem to simply stand around looking confused as to what they did that caused such turmoil.

It might be improper to place too much emphasis on the sexual politics of a movie clearly meant to evoke a bygone era, but the main trouble with She’s Funny That Way is that it attempts to marry this earlier, memorable time of moviemaking with mores and values that probably would not have been used by Golden Age Hollywood. Thus, the movie cannot capture the sparkle of classic screwball comedies and also comes across as anachronistic to modern viewers, particularly in its understanding of prostitution. Is this a reflection of Bogdanovich’s own principles regarding romance and its place alongside work relationships? Of course, one could argue it is merely an inventive way to create a fun story, but given that such ideas stem from Bogdanovich’s personal experiences, what other conclusion can be drawn? By this movie’s token, it seems that he desires to have both a stable loving family (Wilson and Hahn’s children barely register here as they did in They All Laughed) and various dalliances on the side when he needs them. Such vast inclusion could only lead to conflict.

Apart from the sexual politics below the surface, She’s Funny That Way fails to capture the audience’s attention when it needs to most. In the climactic scene, with all the characters in the same room during a rehearsal, the tension that Bogdanovich built over the course of the movie instantly dissipates when a lazy voice-over from Izzy is introduced, followed by a fade to black taking us to the next sequence. A typical montage showing each character getting what they want (or need) wraps everything up but not before we see Quentin Tarantino (a friend of Bogdanovich) bringing much-needed energy and spirit to what would otherwise be a throwaway scene. On top of all this, there is an irritating and completely useless framing device in which Izzy tells this entire story to a journalist asking about how she became a famous actress. Some salt is then put on the wound when the movie ends by showing the scene from Ernst Lubitsch’s Cluny Brown from which the repeated quote Wilson tells his female counterparts originates. What could be more detrimental to a modern-day attempt at screwball than ending with a classic example of the genre, signifying how difficult it is to translate from the Golden Age of Hollywood to today.