5. Crimes and Misdemeanours (1989)
There are two plotlines which run along together, rarely overlapping, but frequently commenting upon and qualifying one another. In one, Martin Landau plays an affluent opthalmologist, plagued by a mentally unstable woman with whom he has been having an affair. Terrified that she will expose him and destroy his comfortable life, he grapples with his conscience as he contemplates employing his criminal brother to murder her. In the other, lighter story, Allen portrays a rather less successful documentary filmmaker by the name of Clifford Stern, hired to make a movie about a jackass comedy producer, Lester (a brilliantly corny Alan Alda). To his chagrin, and despite his many romantic overtures, Lester's assistant producer, Mia Farrow, with whom Clifford is in love, starts to fall for her idiot boss.
Although the murky subject matter might lead one to expect something as melodramatic as Manhattan Murder Mystery, it is the film's total refusal to conform to screenwriting conventions of moral comeuppance that makes it most indelible. With a masterful balancing of sad comedy and banal horror, Allen leaves us with a chilly reminder that the universe is not only a deeply unfair place, but utterly indifferent to our projections of right and justice.
4. Bananas (1971)
Few comedians have the imagination, the consistency or the chutzpah to pull off what is essentially a feature-length sketch show. With this scattershot political/social satire, Allen did exactly that, and the result ranks alongside the best work of Mel Brooks and Monty Python in poking fun at sacred cows and cultural iniquities without ever abandoning the irreverence intrinsic to their charm.
The opening section now looks like a rehearsal for Annie Hall and the relationship comedies of his 'maturity', examining the brief, awkward tryst between blue-collar schmuck Mellish (Allen) and activist Nancy (Louise Lasser, Allen's one-time wife). Mellish, in a moment of lovesick insanity, departs for the fictional 'banana republic' of San Marco, where he ends up serving as an unlikely revolutionary fighter, and being installed as the head of a new and increasingly corrupt regime. From here on out, Allen trains his stand-up honed, rapid-fire sensibility on the evils of dictatorships, and the moral hysteria and hypocrisy of the USA. Sure, the humour is broad, and sometimes reliant upon crude, dated stereotypes, but it remains hilarious from start to finish.
3. Manhattan (1979)
What's left to write about Allen's symphony to his birthplace? It's the visual highpoint, the cinephile's choice, the best NY tourist advert ever made. Whilst Scorsese's 70s output plumbed the bowels of a city on the verge of abject despair, Manhattan keeps its eyes fixed on the skyline, madly in love with the lights. If you're in need of evidence for the importance of the cinematographer's art, the way such a master craftsman can transform the raw material of reality, then take Allen's ode and Taxi Driver, both nominally set in the same metropolis, compare and contrast.
2. Annie Hall (1977)
Richard Curtis, take note: this is how you write a rom-com. Allen's bittersweet tale of stand-up comic, Alvy Singer, reflecting on his failed relationship with the eponymous heroine, is surely the blueprint for aspiring screenwriters everywhere. You'll struggle to think of another example of the genre that more effortlessly balances both essential elements.
The fact that it's hilarious won't come as a surprise: already heated up by a series of deliriously unhinged satires and parodies, by this point Allen's funny bone was practically shooting sparks. Over its tight run-time, little more than 90 minutes, he rattles through more inspired ideas, throwaway gags and set-pieces than Judd Apatow has managed in a half-dozen bloated cinematic offerings.
1. Hannah and her Sisters (1986)
Allen has remarked that it was Diane Keaton's radiant performance in Annie Hall that taught him the importance of giving a full interior psychological life to his female characters - a vital element that he feels was lacking from his earlier efforts. If this is true, then we have Keaton to thank for the subsequent development of one of modern American cinema's finest creators of rich, multi-layered roles for women. In Hannah and her Sisters, Allen's sensitive, compassionate screenwriting reached its zenith.
A chamber drama spread out over a 24 month period, it follows the changing fortunes of three Manhattan sisters and their respective partners as they cheat, bicker, and break apart. The inclusion of veteran Swedish actor Max Von Sydow as one of the sisters' husbands is the giveaway: this is Allen's attempt at emulating the female-centric Kammerspiel of Ingmar Bergman. By keeping their clear-eyed view of everyday human solipsism and weakness, but imbuing the drama with his own type of dizzy warmth, Allen rivals his idol's achievements without succumbing to slavish impersonation.
It could serve as an epitaph for Allen's entire career and the inimitable worldview it has established: the endless, sometimes exasperating marathon of sex, love, death, and life. Only it's still too soon to call time on his 50-plus year legacy just yet...