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8. Stardust Memories (1980)
A beautifully shot film that's as abstract and arty as anything Allen's done, Stardust Memories has a dreamy quality that, perhaps surprisingly, complements Woody's comedy quite nicely. With echoes of Bergman and Fellini, the film follows a director being honored at a film festival as he tries to get the various romantic relationships in his life in order.
7. Love and Death (1975)
This film probably wouldn't even make the top tens of most critics — too silly, too early, too loose when compared with the works of Woody's "serious" period — but it makes me laugh harder and more often than almost any other film I've ever seen. The pinnacle of Woody's early period, Love and Death is a Russian tragedy spoof that's thick with sharp one-liners. "Boris Kruschenkov, you are the greatest lover I have ever had," the beautiful Countess informs Boris (Woody) after a bout of lovemaking. "Well," Boris replies, "I practice a lot when I'm alone."
6. Deconstructing Harry (1997)
The major highlight in the otherwise creatively difficult period that ran from Husbands and Wives to Match Point, Deconstructing Harry is a bitter self-critique about a novelist who pillages his personal life for the sake of his work — and continually incurs his friends' ire for it. The basics of the plot recall Bergman's Wild Strawberries, with the key difference being that Bergman didn't intersperse his picture with scenes of his protagonist discussing prostitutes' blowjob skills with the devil. Comedic interludes like that one are presented as scenes from our protagonist's books, but they play out like stuff from Woody's early career, only darker. Perhaps one of Woody's most personal films, Harry certainly has a sting to it.
5. Hannah and Her Sisters (1986)
Allen's films often involve ensemble casts, but in no film did he work the ensemble better than here, with branches of a family intersecting and diverging like vines. It's perhaps Allen's most humanist film, reasserting the importance of perseverance in the face of adversity. Woody, as a hypochondriac who may actually have a dangerous illness, is particularly touching, and his first date with Dianne Wiest is one of the funniest scenes he's put on film. The ending, in which everything is wrapped up neatly and happily, feels a bit forced, and Allen himself acknowledged as much, saying that the ending of Crimes and Misdemeanors was his attempt to rework the end of Hannah, wherein he "let the characters off too easily."
4. Crimes and Misdemeanors (1989)
In a delicate balancing act, Woody weaves the tragic story of an ophthalmologist who has his mistress murdered with the comedic tale of a documentary filmmaker's battle of wits with his brother-in-law. The twist is that the filmmaker (Woody, of course) is making a documentary about a Holocaust-surviving philosopher (modeled after Primo Levi) whose insights into the human condition explain the decisions made by the aforementioned ophthalmologist. With its stance that the universe is a morally bankrupt place where we must supply our own meaning — and that even doing that doesn't grant us salvation — this is Allen's most ethically rich film.
3. Match Point (2005)
An improvement upon Crimes and Misdemeanors in that the murder in C&M is one of necessity, when in Match Point it's absolutely one of choice. In the earlier film, Judah risks going to jail if he defies his mistress, but our protagonist here risks only having to find a new job. Yet to Jonathan Rhys-Meyers' ambitious social climber, the lure of the good life is simply irresistible. By slightly changing the framework of his previous classic, Allen was able to even better depict the lengths we go to to preserve the realities we've constructed for ourselves.
2. Manhattan (1979)
The apex of Allen's eight-film collaboration with cinematographer Gordon Willis, Manhattan remains the most aesthetically ambitious work in Woody's oeuvre. Shots like the now-famous image of Woody and Diane Keaton looking at the 59th Street Bridge are a reminder of how much dialogue-heavy films like Allen's need a strong visual identity to balance them out. Beyond the superb camerawork, the film marks Allen's first (and most sincere, naïve, and endearing) engagement with personal ethics. The "you'd rather buy the Porsche" speech about integrity is as unforgettable as that moment by the bridge. It's extremely difficult to deal with such issues head-on in cinema, but the humor and cadence of Allen's dialogue makes the film's big themes quite moving.
1. Annie Hall (1977)
What's most incredible about Allen's greatest work — one of the greatest American films ever made — is how natural the stream-of-consciousness narrative structure feels. It takes about ten viewings before you begin to remember which scene follows which, because the cutting serves the workings of memory and characters' associations rather than any linear chronology. It's an experimental film that no one realized was experimental. Of course, structure aside, this film still remains the depiction of how relationships do — and do not — work in the modern era. Effectively the turning point in a career that was moving from zany comedy to dark existentialist drama, this film perfectly blended Allen's absurd humor with his dark take on human nature, by providing the insight that our most irrational needs are often our most strongly felt ones — as evidenced by the joke ("I would, but I need the eggs") that ends the film.