When I was 14, I wrote a letter to Woody Allen.

I’m pretty sure it was a long letter (I never skimped on words), detailing how I wanted to grow up and be just like him. It’s not like I really wanted to be him, per se; I just loved the idea of the freedom he had to make the stories he wanted to tell. See, even then I could tell this was a storyteller not only having the creativity in abundance, but the capability to let that creativity reach its heights.  As an adult, I am even more floored by his ability.

So my letter begged for advice. What did I expect from him? I couldn’t say, I was a kid trying to latch on to some kind of a future, like any typical young teen. Maybe I was hoping he would send me a plane ticket and take me in as an apprentice?  He didn’t write back, of course, but he did send an autographed picture, which I still have today.

There is a chance that Midnight in Paris, Woody’s most recent film will take home the Oscar for Best Screenplay (It is also nominated for Best Picture), and I think well deserved. Of course, Woody won’t show up for the award.  That is not Woody’s way, and I find that also very bad ass.  Simply put, he is too busy making his movies to stop and take an award for the past, he is already on the next story, the future.

These, as a Woody fan, I would recommend as first dips into his library.

The Purple Rose of Cairo

The Purple Rose of Cairo is probably Woody Allen’s best movie.  Beautiful and heart breaking.  This film always feels so delicate to me, like a piece of glassware that could break if tipped just so. In many ways, that could also be used to describe the life of Cecilia (Played by Mia Farrow), an unhappy woman stuck in an unhappy marriage in the unhappy great Depression.

It is also a wonderful film about the power of movies, and what do for us through their escapism.

I don’t want to say too much about this plot, just know it is very highly recommended… by everyone who has ever seen it.

Love and Death

This is the film that made me a fan of Woody Allen. It’s the closest, in my opinion, that an American has come to the brilliance of Monty Python and the Holy Grail.  It’s smart, it’s witty, it’s experimental, and it is very, very silly. You don’t have to know the Russian literature or history he is referring to, but it does add a nice bonus to the viewing.

I used to have sections of this movie memorized when I was a high schooler, confusing many friends and girls on dates, I am sure.

Others may look to Sleepers and Bananas as his best comedies, but when it comes to Woody and comedy this is the bar all the other of his comedies are judged on for me.

Radio Days

Radio Days is, in many ways, Woody’s love song to his childhood in New York, as well as to all the things he loved about that period in history (including, radio and radio stars).

I love this film.  It came out when I was in sixth grade and I am sure I saw it a dozen times through junior high and high school.  It is one of the movies that made me a fan of his work.  Also, it made Woody more real to me. I could relate to the child in this film; meaning that for me, Woody was now more than the comic character I watched in the comedies.  He was human now. This movie is probably also why I have a fondness for old time radio comedies.

Annie Hall

I sometimes like to describe this film as the anti-romantic comedy, which is accurate since we are seeing the end of a relationship, not the beginning.  When I think of Woody writing at this time, he seems like a man on too much caffeine. The amount of ideas and experiments coming from this guy! They are just thrown at you left and right- the narration, interviewing people on the streets, the use of closed captions, I can go on and on… Just an onslaught of creativity.

I love watching Diane Keaton in Woody Allen films, and its hard not to watch this film and have a crush on her. She won the Oscar for this film, and it is richly deserved.

Anyone who hopes to write in film should be required to see this movie and take notes… lots and lots of notes… and there should be a test afterwards… not multiple choice, but with essays.

Mighty Aphrodite

So you adopt a baby and it is the most perfect baby ever. You couldn’t be happier, but a part of you wonders who the real parents are… and you investigate and discover the mom is a porn star.  OK, now take that horrendous revelation and add a classic Greek chorus for the narration and you have one of Woody’s most creative undertakings.

I don’t want to give more away, but I love the storytelling structure of this, and how through all of these large theatrics, Woody keeps this a personal journey for the characters in it.  A great comedy.

Bullets Over Broadway

Another New York period piece (and let’s be honest, Woody always seems more inspired when he is working in a period piece), but this one set around a struggling writer.  It asks a great question many upcoming writers dread having to deal with, the question of art vs. success.  This is the issue David Shayne has to deal with when his play has to take on a questionable actress to make a mafia boss and financial backer happy.

But the story is more than just that! There is also the question of natural talent brought up in the genius character of Cheech.  This is probably Woody’s richest undertakings, with solid characters, a fun plotline with many twists, and the fun setting of  1920’s New York.

Midnight in Paris

Everyone is talking about this movie. Everyone is seeing this movie. So if you haven’t, well, you are alone right now. Alone in the entire world and darkness is seeping in around you. Do you feel it?

Do yourself a favor and rent this film, maybe even buy it.  While some may see this as a just a beautiful postcard of Paris, it is more than that, it is a story about history and the present; and it is that part of the story that got me the most. I love the message of this film.

Match Point

I still can’t believe that this is a Woody Allen film. I’ve seen it three times now, and I am still floored that this is one of his creations.  This was Woody’s first venture shooting outside of America and it began, in many ways a new resurgence in his creativity.  But this story… It’s not a romantic-comedy, this is sexy thriller drama with some seriously dark undertones to it.

It almost makes me think that if Hitchcock was still around and making films this is what he would be doing..  This was also the first movie he made with Scarlett Johansson (they would go on to make three together), and she always seems to do her best work with him, showing an incredible versatility in her different Woody characters.

Other Introductory Recommendations: Alice, Vicki Cristina Barcelona, Melinda and Melinda, Manhattan Murder Mystery, and Hannah and Her Sisters