Below is a photo of me opening a Woody Allen boxset which my colleague Alex took for reasons I can only describe as racist. Allen has pretty much directed one film every year since 1965, with varying degrees of quality. In a double-feature, I’ll start by reviewing one of his best and one of his worst.

Annie Hall (1977)

In his twelfth movie, Allen plays himself perhaps more than ever – a neurotic Jewish stand-up comic called Alvy Singer, who begins a relationship with Diane Keaton’s Annie Hall. I’m not sure this works particularly well as a drama. They’re a difficult couple to like or even care about; they never feel grounded, constantly bickering away in their self-absorbed bubble.

As a comedy, however, Annie Hall hits all the right notes. By playing a stand-up and breaking the fourth wall, Allen manages to weave in his material in a way that never feels contrived. Witty, self-aware and brutally honest, everything Alvy says is funny. Honesty is so crucial to art and to comedy in particular, and this film is disarmingly frank when it comes to issues such as sex and… well, pretty much just sex.

It seems like a huge influence on the brilliant Peep Show, letting the audience in on the paranoid neuroses of the modern urban man as he nervously negotiates his way around women and other men. One scene in which subtitles reveal what the characters are really saying is essentially a proto-Peep Show device and was copied exactly in an episode of Coupling.

Annie Hall is one of Allen’s love letters to New York and gives the film a strong sense of place, providing Alvy with plenty of misanthropic digs at the pretentious urbanites. The comedy fuses bold sex jokes, Jewish paranoia and references to Kafka and Freud, his unique outlook on the world making it hard to see where the next gag will spring from. There’s even an appearance from Christopher Walken, misspelt Wlaken in the credits. By the time they roll, it’s easy to see why this is such a fondly remembered Woody Allen movie.

September (1987)

Less fondly remembered is this stiflingly serious drama from ten years later, about a group of friends discussing their problems in a summer house – nothing to do with the song by Earth, Wind & Fire. This time Allen doesn’t star, because his fumbling around making penis jokes might slightly ruin the sincere tone. But this film is so humourless that a couple of nob gags really wouldn’t hurt.

I know how you feel.

Allen makes dramas as well as comedies, and his best films mix the two – his latest, Blue Jasmine, is a wonderful example of that. So it’s odd that someone who seems so admirably committed to laughing at the world around us and addressing our problems with comedy would make such a depressingly witless movie.

Watching this after Annie Hall, one really begins to appreciate the chemistry between Alvy and Annie. Here, characters might as well be declaring their love for pieces of furniture, as they drably wander around a very drab house. Everyone’s so irritatingly miserable and tediously empty, and as a result, so is the film.

There is, however, a great jazz soundtrack and some notable performances from Mia Farrow, Dianne Wiest and Elaine Stritch. And in fairness to Allen, that’s probably as much to do with his skilled direction of actors as it is their enormous talent. But again, it’s strange that a director and writer so famed for his naturalism and wit would make such a stilted and dour drama.

You too and all.

September has the eerie not-of-this-world feel of a horror film, thanks to the dimly lit house, a Ouija board and Mia Farrow. But also thanks to the way the characters talk like aliens who’ve never heard humans speak before. I’ll leave you with a few lines of dialogue.

• “I’ve wanted to touch your face since the first time we met.” Creepy.
• “How often I’ve wanted to touch you.” Spoken by a completely different character.
• “We’re all temperamental, otherwise we wouldn’t all be so fascinating.” You’re really not.
• “It’s lifeless.” It really is.