Woody Allen's Top 5 Films

We've all been there. Sometimes a film, scene or even single movie quote resonates in such a meaningful, telling manner that it’s altogether frightening how pertinent and apt the message seems. One man's shrewd, poignant, hilarious and secretly romantic films have spoken loudly to me from across that great celluloid divide, forging a deep connection to the material he's so expertly crafted. That man? Woody Allen. I can hear the inappropriate jokes being thought up as I type this but rest assured I’m separating the man from the myth and the auteur from the scandal.

Naturally, I was beside myself when it was announced that Allen’s 40th film, Whatever Works finds the original neurotic New Yorker directing another comedic kvetching genius – Larry David. The forthcoming film also marks Allen’s return to his beloved hometown, after shooting his last three movies in Europe, and marks the perfect time for us to reflect on his abundant output.

So behold, Woody Allen's Top 5 movies...according to me. Agree, disagree, think I missed a masterpiece? Well, don't be shy! Post YOUR number one pick in the comments section below for a chance to win screening passes. Get full contest details here.

Woody Allen Top 5 Movies

5. Deconstructing Harry (1997)

A latter-day Woody gem with all of his hilarious hallmarks taken to the extreme, this dark comedy about a writer who uses his real life as material for his novels wasn’t exactly universally loved but had so many instantly-classic quotes and memorable characters that repeated viewings illustrate why this film is hilarious, crass, far-fetched, surprisingly telling and, of course, 100 per cent Woody. Special kudos for casting Billy Crystal as a Devil who loves to talk shop and Tobey Maguire as a sex-obsessed teen who mistakenly gets claimed by Death.

4. Crimes and Misdemeanors (1989)

Including this Angelica Houston-Martin Landau crime caper inadvertently covers off his 2005 revamp Match Point, as both follow a very similar storyline about a cheating man who can only quiet his conscience by committing murder most foul. Investigating the darkest corners of the human soul without neglecting his penchant for stinging one-liners and clever banter, Allen succeeds in making a thriller that satisfies more than bloodlust and asks hefty moral questions without providing simplistic answers. A must-see.

3. Manhattan (1979)

From its lovely black and white visuals to the much-lauded Gershwin score, Manhattan may be Allen’s most aesthetically gripping film, all gleaming bridges and lovely backdrops. Mining familiar territory – relationships, morality and betrayal – Allen offers a rather sobering take on comedy, playing a twice-divorced man who is dating a high school girl, all the while falling in love with his friend’s mistress. A tempered, nuanced performance by Mariel Hemingway makes for a relationship that doesn’t come off as creepy – or borderline illegal – but ends up being as much about love, misunderstanding and pain as any age-appropriate liaison. Stellar performances by Allen regular Diane Keaton and actor Michael Murphy round out a film that shows a man whose ability to write a pithy quip is on par with his mastery behind the camera.

2. Hannah and her Sisters (1986)

If there’s one thing that ‘70s-era Allen loved more than casting (ex)girlfriends in his films, it was gathering a supremely talented ensemble and letting them work their magic with his witty lines and profound monologues. Filmed as a series of vignettes, the movie follows nurturing Hannah (Mia Farrow) and her aforementioned siblings (played by Barbara Hershey and Dianne Wiest) as they navigate the treacherous paths of love, family and identity in, you guessed it, New York. A fantastic performance by Allen as a paranoid neurotic who was once married to Hannah is matched by a deeply conflicted Michael Caine who plays Hannah’s new man who can’t help falling for one of her sisters. The intersecting storylines of love, lust, mortality and everything in between are handled deftly and don’t shy away from exposing the ugly, and lovely, sides of life.

1.Annie Hall (1977)

The film that set the standard for cerebral, droll, navel-gazing musings on the nature of love, Annie Hall remains Allen’s calling card and my go-to film when trying to convert non-believers. A clever screenplay, which includes such modern-day tactics as direct-address and animation, this 1977 classic earned both Diane Keaton and Woody Allen Oscars, acting for her and directing and writing for him, with Allen even earning a nod for his performance as the deliciously anxious Alvy Singer. Watching the film some 30 years later, Annie Hall is certainly showing her age but the message at the film’s core easily remains modern while the jokes continue to fly off the screen with force and precision. What can I say, I also lurve, luff, loave Annie Hall.

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Now over to you! Share your Favourite Woody Allen movie!