There are a few particular things that are generally known about Herbert Ross’s 1972 comedy Play It Again, Sam: 1. It is obsessed with the characters and story of Casablanca, 2. It is one of the few films starring Woody Allen that was not directed by Woody Allen, and 3. It is named after a line of dialogue that doesn’t exist. That third point is actually sneakily appropriate, as Play It Again, Sam constantly references and infers Casablanca without really getting it.
Woody Allen plays Allan, a Woody Allen-type who is devastated when his wife files for divorce because she isn’t having any fun. Allan is a film critic who is absolutely obsessed with Bogart and Casablanca. As his friends [Diane Keaton and Tony Roberts] try to set him up with the ideal woman, Allan fantasizes a figure of Humphrey Bogart [Jerry Lacy, with a pretty good impression aided by being shot in shadow and out-of-focus] who gives him tough love and classic Hollywood romance advice. Of course part of the joke is that Bogey’s way of talking to women doesn’t really work in 1972 [or at least I hope that’s part of the joke, but with Allen’s history and the way the world still works, I’m not totally sure]. Then there is the gag of seeing and hearing Allan try to be the tough guy in Bogart’s image, a joke that has to cover a lot of ground.
Though Allen didn’t direct Play It Again, Sam, it is based on a play that he wrote, which explains why it feels so much like Allen films to come, especially Sleeper and Annie Hall. As an early Woody Allen film, it is interesting to see that his on-screen persona is already basically complete—he’s neurotic, annoyingly intellectual, and too successful with gorgeous women. The film is so in his voice that though I hadn’t seen it before, I feel like I’d heard all the jokes before.
That doesn’t mean Play It Again, Sam isn’t funny, though it might be a little too much. The entire of runtime of the film involves normal people saying things to Allan and him responding in his trademark caustic, self-deprecating way. At times it feels much less like a script than it does a movie, though this changes in the second act when the plot shifts to a possible romantic encounter between Allan and his best friend Linda. Really, though, the flights of silliness, including the Bogey fantasies are the film’s highlights. Even if Play It Again, Sam isn’t going to connect on any real level, there are moments. Who cares if Allan and Linda inexplicably end up together, but the Italian Neorealism fantasy or a gag when Allan dials the wrong number are fun.
As for the connections to Casablanca, there are actually fewer than I expected. The Bogey fantasies serve as the film’s high concept plot, but it ends up being more of a sometime plot contrivance than anything. Bogey guiding Allan through making a move on Linda remains one of the films best moments, though. Even still, much of the Bogey persona in Play It Again, Sam isn’t just reduced to Rick Blaine, even though that is the role that inspires the characters look—much of his sensibility and manner of speaking comes from his detective films like The Maltese Falcon and The Big Sleep. The idea of Casablanca actually doesn’t have much to do with the tone or narrative of Play It Again, Sam. The only direct connections are intercuts of Rick and Ilsa’s famous kiss with Allan and Linda’s first kiss and the final scene’s location at an airport hangar.
So, despite being reminded of Casablanca multiple times [the opening scene literally just being the ending scene of Casablanca, the giant poster in Allan’s living room, etc.], Play It Again, Sam only really uses the classic film as window dressing. Because of that, Play It Again, Sam comes off as a novelty. It is a unique plot device [the only other film I can think that builds with another film in this way is, strangely enough, Paris-Manhattan, a small French romantic comedy that uses Manhattan in a similar way that Play It Again, Sam uses Casablanca] but a novelty nonetheless.