Here are two more Woody Allen films – like last time, one of his best and one of his worst.

Manhattan (1979)

Shot in beautiful black and white and set in – get this – Manhattan, this is Allen’s ninth film and sees him play a divorced writer named Isaac who’s having an affair with a 17-year-old. He’s playing himself again but it works; these films aren’t about his acting or even the plot, they’re about relationships, people and talking.

The plot’s similarities to subsequent events in Allen’s personal life are unfortunate and the film never really addresses the inappropriateness of a 42-year-old dating a 17-year-old. And quite how he repeatedly attracts such good-looking women is beyond me, I guess funny really is sexy. But the fact that none of this ever gets in the way is testament to just how good this film is.

Once again, the dialogue is the heart of this movie and it’s rich with insecurity, self-awareness and cultural references, from Lenny Bruce to Ingmar Bergman. It’s also laugh-out-loud funny, the rhythm of the neurotic rants, the witty turns of phrase and the tiny incidental moments providing the film with plenty of laughs. The insecurity of Allen’s characters makes them feel vulnerable and human, with the superb Diane Keaton matching his own trademark neuroticism.

There’s even a profundity to his writing, which never feels pretentious – in fact much of Manhattan is spent railing against pretentiousness, as in Annie Hall. While the dialogue is profound, it remains believable and true to the things that people actually say, which is an impressively rare combination lacking from many films. Films like The Counselor.

Manhattan‘s enormous influence is clear to see, notably on Peep Show again but also on New York comedies like Friends and Louie – Louis CK would later work with Allen in Blue Jasmine. Like those shows, Manhattan makes New York almost into its own character as Allen recreates the jazzy atmosphere of the New York films he loves.

Allen is a paradoxical man; romantic but cynical, whose writing is profound yet grounded and whose films are both comedic and tragic. More so perhaps than Annie Hall, this movie brilliantly toes that line between comedy and drama and reveals just how expertly Allen juggles all these different elements. And then there’s the sheer acting of Meryl Streep.

Melinda and Melinda (2004)

25 years later comes this mash-up of Sliding Doors and Blue Jasmine, which opens with a conversation between a bunch of writers who ask the question: Which is the best way to deal with life’s dramatic events, comedy or tragedy? This leads to a comedy writer and a tragedy writer each giving their own version of the same story, involving a woman named Melinda (Radha Mitchell). We see her story play out in two versions – one a comedy, the other a tragedy. As I said, Sliding Doors. And as in Sliding Doors, one of the major differences between the two stories is that the main character’s hairstyle is conveniently different.

The film’s initial failing is this contrived premise, which feels more like a writing exercise than a proper narrative. Having praised the believability of the dialogue in Manhattan, it’s odd to see this laboured set-up which really doesn’t ring true. One reason that people take so strongly against Allen’s bad films could be that they undermine his good films – last time I complained that the dreary humourlessness of September was completely at odds with the lightness of touch that characterises Annie Hall, and here it seems that this pretentious premise conflicts with the anti-pretentiousness of Manhattan.

This premise also has three unfortunate consequences. The first is that it gets in the way of the actual stories, which are each only 45 minutes long. In the tragedy, the characters aren’t properly developed and none of it really has much of an impact, while in the comedy, it’s simply not particularly funny with Will Ferrell taking on the Woody Allen role and gurning his way through recycled jokes from Annie Hall.

Secondly, the film lurches from the tragedy to the comedy and back again with an irritating frequency, so just as we’re getting into one of the stories we’re jerked awkwardly into a completely different film. This makes it rather like Cloud Atlas; one moment you’re watching an emotional drama and then suddenly you’re watching a wacky farce.

Thirdly, we know exactly how each story is going to turn out – the comedy will end happily and the tragedy sadly, by definition. I thought Allen might subvert this and flip the endings or something in an “ahhh” moment, which would have been just as annoying. But that doesn’t happen, and – spoiler alert – they end up exactly as we expect.

Melinda and Melinda always feels forced, from the premise to the performances, while Allen’s best films manage to feel completely natural. It asks an interesting question but in a ridiculously clumsy way. What’s more, it’s a question that he’s answered numerous times by this point: Which is the best way to deal with life’s dramatic events, comedy or tragedy? The answer for him is with a combination of the two, and again his best films manage that. He would go on to tackle a similar story in Blue Jasmine, and rather than leap awkwardly between comedy and tragedy, it would fuse the two in a way which harks back to his masterpieces like Manhattan.