5. Play It Again, Sam (1972)
Originally a Broadway show penned by Allen, he adapted 'Play It Again, Sam' for the big screen, resulting in perhaps his first 'serious' comedy. The film still contains comical slapstick moments as seen in his previous works, but the plot has a more thoughtful tone - featuring infidelity, love and the complicated shackles in life. Although Allen wrote and starred in the film, it was directed by Herbert Ross. Set in San Francisco, the story follows Allan Felix (Allen), a recently divorced prescription-pill popper who writes for a movie magazine. Allan adores the classic film 'Casanova', especially the protagonist played by Humphrey Bogart. Throughout the film, Bogart appears as a ghostly figure in front of Allan, offering him advice on women and life. Woody Allen has used this kind of escapism many times in his movies, 'The Purple Rose of Cairo' for example, and more recently in 'Midnight In Paris'. Allan Felix has two great friends who happen to be a married couple - Linda (Diane Keaton) and Dick (Tony Roberts). The pair decide to get Allan back on the dating scene, setting him up with numerous women, resulting in a string of disastrous dates in which Allan plays the bumbling bachelor instead of portraying the cool, calm, no nonsense ladies man persona preached to him by Bogart. Eventually Allan falls for Linda and they plan to become an item, but after a brief swapping of emotions she decides to stay with Dick and speeds off to catch up with him before he departs on business. Allan follows Linda in the hope of winning her love but concedes defeat in the end as Dick and Linda embrace on a foggy airfield. The scene mirrors the ending of 'Casablanca', with Allan quoting from the famous film. A funny, intelligent comedy expressing how people strive to be something else in life, 'Play It Again, Sam' is a Woody Allen classic.