Finally, after a couple of false starts, Woody Allen debuts as cinema’s greatest writer/director/actor. This is a lofty title, although there’s been virtually no one since the silent era to contest it. The list of great writer/directors is long and prestigious. The list of actor/directors is shorter, and the list of great writer/actor/directors is so short, you’d probably end up having to include Ben Affleck just to fill out a top ten.

Take the Money and Run was released in 1969, three years after Woody Allen’s last film appearance (in Casino Royale). During that time, he was very busy with stand-up comedy, commercials, Broadway productions and television appearances.

Woody Allen was definitely a celebrity by now. But like Charlie Chaplin circa 1935 or Zach Galifianakis circa 2011, he was mostly known for wacky antics within the confines of a well-known, much-adored character. This makes Take the Money and Run notable not just because it’s his first starring role, or his first movie as a writer/director, but also because it’s the first time he started to branch out of his popular Woody character, even just a little bit. Take the Money is a slapstick comedy, but it occasionally finds time for real characters and genuine sadness in between the gags.

Take the Money and Run is a “documentary” about Virgil Starkwell (Allen), an incompetent criminal who adheres to a life of crime despite never having succeeded at a single criminal venture. The film opens with a synopsis of Virgil’s childhood — bullied, ignored, beaten up, etc. It shows repeated instances of bullies removing his glasses and stepping on them, a joke that gets repeated throughout the film — first bullies, then cops, and then judges.

In his late teens, he starts with petty crimes like stealing purses and robbing pet stores, eventually working his way up to bank robbery. Along the way, he makes a couple trips to jail, and he meets and falls in love with a woman named Louise, played by the absurdly pretty Janet Margolin.

This movie is widely credited as the first ever mockumentary, a genre that later included This is Spinal Tap, The Office and Allen’s own Zelig. It’s a fairly ingenious move that takes otherwise ridiculous antics and forces them into a real-life context via the world’s most straight-faced film form, the documentary. This is Spinal Tap, which made even better use of the genre, “captures” its moronic band members in their every day life, interacting with supposedly real people and extolling, in their own words, the virtues of their music (and their amps). This genre also provides a narrative short-cut by giving the characters the ability to talk with a documentarian or directly to the audience, allowing them to spell out their feelings and stories in a way that might otherwise feel forced or unrealistic.

Take the Money uses the format to speed through extraneous plot details — for example, Louise’s entire back-story, Virgil’s prison sentences, and many other details are explained swiftly in documentary voice-over — allowing Allen to maximize the film’s brief running time. It also allows for “interviews” with significant people in Virgil’s life, namely his parents, who wear fake noses/mustaches to disguise their identity.

I have so far criticized every movie on this site for seeming disjointed and lacking cohesion. This being another gag-based slapstick comedy, the same is true, although unlike Casino Royale which felt cynically slapped together, Take the Money is enjoyably anarchic. It is also much funnier than any other movie he had yet appeared in. Woody Allen’s first appearance in the movie — as a fumbling cellist trying to fit into a marching band — is funny in a fast, lightweight way that is completely antithesis to the dreary bloat of Casino Royale.

In his next movie, Bananas, Allen starts to find humor in broader ranges of topics — politics nationalism, religion. But here, he uses himself as the butt of most of the jokes. He humiliates himself in front of his prison friends when they employ him as an ally in a break-out attempt but forget to tell him when they call it off. Far from the intellectual heart-throbs he started casting himself as in the ‘80s, Virgil Starkwell is firmly in lovable loser territory. Allen attempts to stage a bank robbery, but his timidity and incompetence prevents him not only from succeeding, but from properly initiating.

It’s mostly light-hearted, but there are emerging elements of the sincere self-loathing that pops up increasingly in Woody Allen’s film career. In a scene that mirrors Allen’s famous verbal take-down at the hands of Meryl Streep in Manhattan, a woman in an on-screen “interview” re-counts how overwhelmed she was by his profound idiocy. Knowing it was written and directed by Allen, it feels humorously self-deprecating at first, but goes on and on, increasing in specificity, until it ends up verging on cruelty. And for added masochistic value, that woman is played by Woody Allen’s real-life wife.

Another recurrent theme foreshadowed is Allen’s love/hate relationship with his hero/tormenter Sigmund Freud. In a very funny conversation that quickly captures the ridiculous but overbearing nature of psychoanalysis, Virgil’s analyst explains how the seemingly innocuous act of playing the cello was a way for Virgil to symbolically express sexual interest in his mother.

I mentioned that this is Woody Allen’s first venture outside his comfort zone, which may not be apparent from any of the above descriptions. His character, however, is not the frantic explosion of angst it was in Casino Royale or What’s New Pussycat. As a beaten-down, working class criminal, he strips away some of the nervous energy and lets himself be genuinely melancholy in moments. At one point, he and his wife eat a single piece of salami as if it was a real meal. It’s a scene clearly inspired by Charlie Chaplin’s famous shoe-eating scene in The Gold Rush, and it is similarly effective at showing a simple, desperate man trying to trick himself into thinking he’s satisfied.

The movie seemingly aims low — for goofy laughs — but there’s barely a minute that isn’t funny, good-natured and entertaining. Just like Spinal Tap, Take the Money and Run may not change the way anyone looks at the world or thinks about life, but it makes a convincing argument that, to be considered a classic, maybe it’s good enough to just be very, very funny.

Memorable Woodyisms

• “I knew it was love, because right away I started to feel nauseous.”
• “No prison can hold me! I’ll get out of this one if it means spending my entire life here.”
• “Virgil complains, and he is severely tortured. For several days, he is locked in a sweat-box with an insurance salesman.”
• “He is always very depressed. You know, he never made the ‘ten most wanted’ list. It’s very unfair voting, it’s who you know.”
• “Crime is a great job, the hours are good, you’re your own boss, you get to travel a lot, meet interesting people. I just think it’s a good job in general.”

Fun Facts

• Some reviews claim Allen is partially doing a comic twist on Dostoyevsky’s Crime and Punishment, a book I should probably read at some point.
• Like What’s Up, Tiger Lily?, this movie was also chopped up by the studio, trimming it in length by over 15 minutes. The difference is, this time, Allen thought the cuts improved the film and the man who cut it, Ralph Rosenblum, was hired on as editor for Allen’s subsequent films.
• Woody Allen originally wanted Jerry Lewis to direct, but he turned it down.
• This movie was filmed in San Francisco, likely giving Allen ammunition for his scathing portrayal of California in Annie Hall.
• The psychiatrist’s name is Julius Epstein, the same name as Casablanca’s screenwriter. This is the first indication of Allen’s love of Casablanca. The next would come more blatantly in the form of his 1972 movie Play It Again, Sam.