1. Crimes and Misdemeanors (1989)
Woody Allen's hilarious treatise on moral responsibility remains just as devastating almost 25 years after it was first released. The film focuses on Martin Landau's doctor, who ponders having his mistress (Anjelica Huston) murdered after she starts blackmailing him. Allen generates huge laughs co-starring as a documentary maker commissioned to make a film about a man he despises (Alan Alda). Allen revisited the themes of this film with younger protagonists in 2005's Match Point, and while that film isn't without merit, it doesn't come close to Crimes and Misdemeanors' deft combination of nimble character comedy and dark moral exploration. Watching this again recently, I felt like it provided a slightly more pragmatic alternative to the black nihilism presented by the Coen brothers in the films No Country For Old Men and A Serious Man.
2. Hannah and Her Sisters (1986)
The Annie Hall to Crimes and Misdemeanors' Manhattan, this triple Oscar-winning masterpiece is a gentler film that overflows with familial warmth and literary romanticism. Three tales are told over the space of a year, all within the context of Allen's fantasy New York, filled to the brim with intellectuals; artists and second-hand book shops. Arguably Allen's best ever leading man that wasn't him, Michael Caine is utterly delightful as the overlooked patriarch contemplating an affair with a never-more-alluring Barbara Hershey. Dianne Wiest generates just as many laughs as a former party girl trying to make a go of things. Caine and Wiest both deservedly won Best Supporting Actor Oscars, with the third going to Allen for Best Original Screenplay.
3. Manhattan (1979)
Shot in gorgeous black and white, this enduring classic opens with jokes about how its protagonist over-romanticises New York, then proceeds to present the most unabashedly romantic view of the Big Apple ever put on screen. Too easily dismissed as a remake of my pick for No. 4, I consider Manhattan to be Woody Allen's most elegant movie. Although it sometimes feels like he made the film specifically for the viewers left crestfallen by Annie Hall's somewhat cynical ending, this isn't the happy ending version of that movie - it's a masterful comedy in its own right in which every single shot looks like a frameable photograph.
4. Annie Hall (1977)
The film where Woody Allen's filmmaking talents really came together properly for the first time and set the tone for all of his works to come. It was a breakout hit and won four Oscars - Picture, Screenplay: Director and Best Actress for Diane Keaton, whose titular character became a style icon. Famously, the plot of Annie Hall originally concerned its leads investigating a murder - a thread completely abandoned in the editing room. I like to think that the experience proved to Allen that his films didn't need to be about anything beyond their characters and their interactions. The jokes in Annie Hall hold up amazingly well, and its variety of narrative techniques still seem innovative today. He revisited the murder idea with 1994's Manhattan Murder Mystery.
5. Broadway Danny Rose (1984)
One of my favourite things about Woody Allen's career is that by sheer virtue of its longevity, he serves as an access point into 'old showbiz'. Broadway Danny Rose is Allen's heart-warming ode to a long-faded part of the entertainment, and takes the form of a series of anecdotes told by various (real) talent agents as they chow down on pastrami sandwiches at New York's iconic Carnegie Deli. Their stories are about the titular figure, a perennially downtrodden fellow agent whose clients barely qualify as "entertainers". The black and white film is overflowing with both love and wonderful comedic set-pieces, none more legendary than the helium-infused shoot-out inside a warehouse full of parade balloons.
6. Deconstructing Harry (1997)
It's often unfairly lumped in with Allen's lesser films, but I adore this amusingly profane film and watch it regularly. 1980's self-referential Stardust Memories coyly addressed the presumption that Allen's work is autobiographical, but this mines a much funnier film out of the topic. There are two actors for every character in the film - one for the "real" scenes, and one for parts of the film that represent Harry's autobiographical novels. It's very cool. The short section of the film involving Tobey Maguire and the Grim Reaper is probably my favourite Woody Allen set-piece ever.
7. Blue Jasmine (2013)
I was so blown away by this new film I had to include it here. It's a collision of new and old Woody Allen styles that nevertheless plays out with seamless joy. The social context of Blue Jasmine is somewhat out of time, but the story is never once undermined. The characters all pop amusingly and Cate Blanchett delivers one of the greatest ever Woody Allen lead performances. Allen's knack for ingenious casting is in full effect too, with marvellous supporting turns from foul-mouthed '80s comedian Andrew Dice Clay (The Adventures of Ford Fairlane) and arguably the top comic in the world today, Louis CK. Do not miss this movie! Even if you hate Woody Allen. He's not in it! And although Allen fans will find much to enjoy, you wouldn't necessarily peg it as a Woody Allen film if you didn't know it was one.
8. Vicky Christina Barcelona (2008)
Woody Allen pretty much invented the modern romantic comedy, and this film proves he can still pull off a prime example with aplomb. It also proves just how much sway he has with actors - this stars arguably the three most beautiful actresses in the world today - Penelope Cruz; Scarlett Johansson and Rebecca Hall, all three of whom have never been better. Plus it demonstrates how purely romantic the filmmaker can be when he wants to - even when there's a cynical sting in the tail. All of Allen's imitators forget that last part.
9. Husbands and Wives (1992)
Overshadowed at the time of its release by the connection between Allen's personal troubles and the plot of the film, Husbands and Wives holds up extremely well on repeat viewing. It's on this list primarily due to the insanely funny performance from late film director Sydney Pollack as a middle-aged man who starts to regret leaving his wife (Judy Davis) for a younger woman (Lysette Anthony). But the rest of the film is fantastic too, especially Juliette Lewis as a wannabe writer who gives poor feedback. One of Allen's more underrated films.
10. Celebrity (1998)
I've never understood the toxic reputation this film enjoys - it's freaking awesome! Some viewers were put off by Kenneth Branagh's Woody Allen-ish character, but I enjoyed him a lot here. And Judy Davis, a Woody Allen stalwart who never fails to deliver, has a great arc as well as Branagh's ex-wife. Charlize Theron is awesome too in an early role. The scenes of Leonardo DiCaprio as a young Leonardo DiCaprio-esque star partying with his entourage are informed both by reality and the presence of Entourage star Adrian Grenier in said entourage. Celebrity is another example of how Woody Allen is one of the few filmmakers working today who can make black and white work for him. It's also damn funny.
This was really difficult. Other Woody Allen favourites of mine include Bananas, Sleeper, Zelig,The Purple Rose of Cairo, Radio Days, Small Time Crooks, Sweet and Lowdown, Bullets Over Broadway, Everyone Says I Love You, Anything Else, Match Point and Midnight In Paris.
* Woody Allen fan? Agree? Disagree? What are you favourites? Looking forward to Blue Jasmine? Comment below!
