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When looking at Woody Allen’s first set of films, I am often surprised how different they are from what I had been expecting. When the soon-to-be prolific filmmaker began his career in film, the nuanced dialogue and cerebral joke-writing that would become Allen’s trademark in masterworks like Annie Hall (1977) and Manhattan (1979) were nowhere to be found. Instead the writer/director’s early films rely heavily on slapstick, wacky sight gags and jokes that seem pretty corny by today’s standards, up to and including Every Thing You Always Wanted to Know About Sex * But Were Afraid to Ask (1972) and Sleeper (1973). At his core, Allen has always been a Marxist comedian (as in Groucho, not Karl) but unlike his comedy progenitors who used the topic of sex as a means toward a good laugh, Woody Allen’s focus as a storyteller has always been the reverse; to use a good laugh to reveal some unspoken truth about the relationship between men and women and its profound ridiculousness.

The first feature with Woody Allen’s name all over it, What’s Up, Tiger Lily? (1966), is furlongs ahead of its time in terms of the re-appropriation of films for new creative uses as well as the now commonplace video-culture practice of mining the unconvincing and the unremarkable for unintended entertainment value. The subject of Allen’s mockery is a cheeky Japanese spy movie directed by Senkichi Taniguchi, “Kokusai himitsu keisatsu: Kagi no Kagi” released with the English-language title Key of Keys (1965). After acquiring Key of Keys, the president of American International Pictures became concerned by the film’s overall terribleness and latched on to the idea of changing it into a comedy by recording newly written dialogue. The English title refers to the microfilm which serves as the screenplay’s MacGuffin, however in Woody Allen’s comedy overdubbing, the closely guarded government secret contained on the microfilm is changed to the world’s greatest recipe for egg salad. As most of us who have caught a Godzilla movie on television can confirm, there is something inherently funny about foreign movies that have been dubbed-over. Whether it’s the badly-worded translation or the less-than-convincing performances from the voiceover actors, a poorly dubbed movie creates an absurd incongruity between what is being seen and what is being heard – and this specific kind of ready-made ridiculousness is the genesis for Allen’s first film. Although the film disappoints in the laughs department, Allen’s multilayered approach to the medium begins a career-spanning tendency toward movies about the movies; a style more fully fledged in later works such as Play It Again, Sam (1972) and The Purple Rose of Cairo (1985). When watching What’s Up, Tiger Lily? now, the postmodern comedy treatment no longer seems as fresh and innovative as it once may have, since comedy overdubbing has become a ubiquitous practice in the digital age, and as a result the majority of the jokes come across as unexceptional. To further confuse matters, the comedy is peppered with jarring music and dance sequences featuring the 1960s pop group The Loving Spoonful (apparently added without Allen’s permission) as though the band has been transplanted in from a teenaged beach party movie. As a comedy project, What’s Up, Tiger Lily? is doomed by its studio-conceived concept. Despite the admirable efforts of a young comedy genius, the boring pace and unimpressive visuals of the original Key of Keys spy flick makes What’s Up, Tiger Lily? an inauspicious first try for Woody Allen.

What’s Up, Tiger Lily? has much in common with another disappointing spy spoof Allen worked on the following year; the entirely incomprehensible James Bond comedy Casino Royale (1967). With five directors and at least four comedians all playing competing versions of 007, including David Niven and Peter Sellers, Casino Royale is nothing short of a rambling mess which fails at following the trend established by A Shot in the Dark (1964) and The Pink Panther (1963). The James Bond comedy can boast and all-star cast including John Huston as M and Orson Welles as the villainous LeChiffre however it is a shame that, with all this talent invested in it the parody, the film isn’t able to produce more laughs. Some of the funniest lines come from Woody Allen playing an uncharacteristically anxious and craven interpretation of 007 and, although Allen is not credited as a screenwriter, some the lines he performs are clearly of his own invention. In a scene that could have been from Allen’s Bananas (1971), Woody is being taken before a South American firing squad and ineffectually bargains for his life by saying “Listen, you can’t shoot me. I have a very low threshold of death. My doctor says I can’t have bullets enter my body at any time.” Evident in both What’s Up, Tiger Lily? and Casino Royale is that it takes Allen some time to evolve beyond his roots in television comedy, as both movies seem like the kind of idea that would have made for a solid sketch on “The Sid Caesar Show” or “The Colgate Comedy Hour” but are unworthy of a feature length treatment. A major problem with both films is that the jokes are pointed at the easily mocked hyper-reality of spy movies which negate Allen’s enormous talents in exposing the absurdity of the interpersonal.

After all these misfires, the first real Woody Allen film is Take the Money and Run (1969) as it is the first to be written, entirely directed and star the young comedian – And for my taste it is also the best written and consistently funny movie of his early career. Similar to the spy spoofs, Take the Money and Run also reflects a filmmaker deeply enamoured with film culture, as well as the opposite sex. The film is a fictionalized documentary about the world’s most inept criminal (played by Allen) complete with a hardboiled voiceover which unsuccessfully attempts to characterize the nebbish Allen as a dangerous outlaw. When object of Allen’s affection appears during a botched purse-snatching in Central park, the film’s narration changes an internal monologue by Allen, allowing for such exceptionally written lines like “After fifteen minutes I wanted to marry her, and after half an hour I completely gave up the idea of stealing her purse.”

Toward the end of Take the Money and Run, this intensely unsuccessful career criminal robs a man at gunpoint before realizing his intended victim is an old acquaintance of his and the two fondly reminisce before Allen reminds him to hand over his wristwatch as well (which he happily does). In the hands of a young Woody Allen, the juxtaposition of the mundane social interaction with the life-or-death event of an armed robbery creates an absurd reflection on society that is as hilarious as it is brutal. The ease with which both characters are able to immediately separate the mugging from the pleasant stroll down memory lane gives the scene a slightly surreal quality which is on par with the filmmaker’s best moments. In Allen’s next film Bananas (1971), there are one or two similar scenes which are built around a bizarre juxtaposition that would be completely at home in a Luis Buñuel film. After a difficult breakup, Allen’s character visits with is overbearing Jewish parents to explain he wants to travel to find himself. His parents express disappointment and encourage him have another try at medical school, all while they perform surgery on a conscious patient and eventually urge him to take over the medical operation from his father. Once again, it is the normalcy with which everyone (including the patient) treats this entirely absurd social interaction that gives this scene its razor-sharp comedic edge.

Allen’s profound ability to humorously contrast the mundane with metaphysical concepts of death, religion or philosophy is what has always set him apart as a filmmaker and as a writer. Take the Money and Run contains tangential line which perfectly encapsulates a certain Woody Allen formula for joke writing; when discussing the unseen character of Allen’s mother-in-law, the narrator relates in a deeply serious voice that she “claims to have conversations with God in which they discuss salvation and interior decorating.” In his best work, Woody Allen’s absurd juxtapositions between the commonplace and the all-encompassing achieve the highest function of comedy; the insinuation of profound truths that cannot not be said by anyone taking themselves seriously.

What’s Up, Tiger Lily? (1966), Bananas (1971), Play It Again, Sam (1972) and Casino Royale (1967) are all currently available through Netflix in Canada.

Original Artwork by Bennett O’Brian