The comparison may sound outrageous, but the film personality whom Woody Allen most resembles is perhaps Clint Eastwood. And vice versa.

Think about it: They both began by acting in low-brow, mass-market entertainers, Allen in banana-peel slapsticks, Eastwood in spaghetti westerns. They both baffled their fans by suddenly transforming themselves into directors of high-brow cinema. They have both won four Oscars, including Best Director. They’re both multi-talented amalgams of actor, director, producer, musician and composer, with a passion for jazz. They’re now both in their 80s and still active, as producers and directors. (In fact, they’re both listed among the oldest Oscar winners of all time, having won Oscars at the ages of 76 and 74, respectively). They both have a hard-core cult following of their previous avatars, of which they’re now rather embarrassed. One could go on.

Now Allen is in the news again, with his latest film, Café Society, which will open the Cannes Film Festival this year. The film is a romantic comedy set in the Hollywood of the glittering 1930s and the café society that was its cultural heart. It stars Kristen Stewart and Jesse Eisenberg. But let’s take a look at the filmmaker, who has, remarkably, made 48 films in the last 50 years.

Woody Allen began life as a gag-writer for various well-known comedians at the age of 15. And he was hugely prolific: in one year alone he is said to have written over 20,000 one-liners. As a result, while still in his teens, he was earning more than both his parents combined. After high school, he briefly studied communication at New York University before, ironically, failing the Motion Picture course, and dropping out. But by then, inspired by the wacky humour of SJ Pereman and the Marx Brothers, he had began a long evolutionary process: stand-up comic, host of his own comic TV show, playwright, actor, cartoonist and short story writer (for the New Yorker), and film scriptwriter.

As a stand-up comic Allen was hugely influential in the America of the 1960s, with his unique style of the neurotic Jewish nerd (a style that, interestingly, was merely an act: in real life Allen was, apparently, a tough kid and something of a baseball star).

The first film script Allen wrote, in 1965, was What’s Up, Pussycat? starring Peter Sellers and Peter O’Toole. But, frustrated by what he saw as lacklustre direction that let down his film badly, Allen then took to directing his own films. And he’s never looked back since.

‘What’s Up, Tiger Lily?’

His first film, which he both scripted and directed, was the wildly inventive What’s Up, Tiger Lily?: basically a B-grade Japanese spy movie, which he dubbed over with a hilariously zany new English dialogue. This led to a series of manic, off-the-wall comedies whose humour was rooted in a mixture of nerdiness, angst and existentialism, mixed liberally with sexual frustration. For example, in Play It Again, Sam, Allen plays the part of a recently divorced guy who tries to pick up a woman who is looking at an abstract impressionist painting at an art gallery. As a pick-up line, he asks her what the painting means to her.

Clearly emotionally disturbed, the woman replies, "It restates the negativeness of the universe. The hideous, lonely, emptiness of existence. Nothingness. The predicament of man forced to live in a barren, godless eternity like a tiny flame flickering in an immense void…."

Eagerly, Allen asks her, “So what are you doing Saturday night? “

"Committing suicide," she relies, bleakly.

He, without missing a beat, asks, "OK, so what about Friday night?"

This was the brand of humour that would run through Allen’s hugely popular films of the ‘60s and ‘70s, films like Take the Money and Run, Bananas and Everything You Always Wanted to Know About Sex, Sleeper and Love and Death.

In Love and Death, for example (a spoof on the works of Dostoevsky and Tolstoy), the heroine says, "Sex without love is an empty experience."

And the hero replies, "Yes, but as empty experiences go, it's one of the best.”


In the late 1970s, however, a whole new kind of Woody Allen began to emerge – a Woody Allen who had discarded his wacky comedies for a sophisticated style of filmmaking, inspired by European directors like Ingmar Bergman and Federico Fellini. The turning point was in the years 1977 to 1979, during which he made Annie Hall, Interiors and Manhattan.

‘Annie Hall’.

It was a transition that Allen later parodied in Stardust Memories (1980), in which he plays a successful comic filmmaker (evidently himself) who doesn’t want to make funny movies any more. A running gag through the film has various fans coming up and telling him that they love his films, “especially the early funny ones”. That gag officially acknowledged the end of the old Woody Allen, and the birth of a new one – one who would, for the next several years, alternate between serious, philosophical dramas and European-flavoured comedies (also suffused with philosophical undertones).

Or, as his old fans would say, it was the end of the good old Woody Allen, and the birth of a pretentious new one.

But Allen, not unlike his wonderful character, Zelig, the human chameleon, just kept on morphing, kept on getting better. In fact, a quick look at various critics’ shortlists of Allen’s best films reveals that most of them date from the period beginning 1995 – when he was 60, an age when most people would start thinking of retiring to Florida. In Allen’s case, however, this was the period when he made little gems like Mighty Aphrodite, Sweet and Lowdown, Match Point, Cassandra’s Dream and Midnight in Paris.

It was also, significantly, a period when his audience shifted increasingly from the US to Europe – one of the reasons being, as Allen once rued, that America is losing its taste for small cinema, and American studios are now interested only in producing $100 million movies that will make $500 million in returns.

‘Midnight in Paris’.

Allen’s record is enviable. He has so far won four Oscars – one for Best Director, and three for Best Original Screenplay (in fact, he has been nominated for an Oscar 24 times: 16 times as a screenwriter, seven times as a director, and once as an actor). Annie Hall has been ranked #35 in the American Film Institute’s list of the 100 Best Movies of All Time, and #4 in its list of 100 Best Comedies. Allen has won a special Lifetime Achievement Award awarded by the Cannes Film Festival, as well as a Career Golden Lion by the Venice Film Festival. And now, at the age of 80, he’s still going strong – and still in the market for more awards.

So what accounts for Allen’s genius? The person who understands best is perhaps Diane Keaton, who acted in eight of his films, including his masterpiece, Annie Hall (and was also his partner for many years). As she puts it, “He has a mind like nobody else. He is bold. He’s got a lot of courage in terms of his work. And that is what it takes to do something really unique, along with his genius imagination.”

But, to come back full circle to where we began, there’s yet another curious parallel between Allen and Eastwood: they both have an unlikely James Bond connection. Eastwood turned down the offer to play James Bond after Sean Connery quit the role, while Allen acted in the spoofy 1967 version of Casino Royale, playing the part of double-agent Jimmy Bond. It’s a subject one could perhaps do a PhD on.