Essay
Where should you start with Woody Allen?
Fifty feature films, more than six decades and a career that moves from romantic comedy to murder, morality and the meaning of life. Five films that offer a way into Woody Allen's cinema.
If you're new to Woody Allen's films, I'd recommend starting with Annie Hall (1977), Manhattan (1979), Hannah and Her Sisters (1986), Crimes and Misdemeanors (1989) and Midnight in Paris (2011).
They aren't necessarily his five greatest films, although several would certainly appear on my personal list. What makes them useful as an introduction is how different they are from one another.
The obvious place to begin might be Annie Hall, the film that won four Academy Awards and established Allen as one of America's leading filmmakers.
But his career is far too varied to be represented by a single film.
Someone who enjoys the romantic fantasy of Midnight in Paris might be surprised by the bleakness of Interiors. A viewer introduced to Allen through Sleeper could find Match Point almost unrecognisable as the work of the same director.
Comedy, relationships, philosophy, nostalgia and the fear of death all appear throughout his work, but rarely in quite the same combination.
These five films provide different ways into that world.
1977 · Annie Hall
The film that changed romantic comedy.
If you're going to watch just one Woody Allen film, Annie Hall is probably the place to begin.
Allen plays Alvy Singer, a neurotic New York comedian whose relationship with the free-spirited Annie Hall, played by Diane Keaton, provides the basis for one of cinema's most inventive romantic comedies.
What makes Annie Hall remarkable is the way it tells its story.
Rather than following a conventional narrative, Allen moves backwards and forwards through Alvy's memories, breaks the fourth wall, introduces animated sequences and allows characters to step outside their own experiences to comment on them.
The famous scene in which Alvy produces Marshall McLuhan from behind a cinema queue remains one of the funniest examples of Allen's willingness to play with the rules of filmmaking.
Yet beneath the jokes, there's a genuine sadness.
Alvy and Annie are attracted to one another, but their differences become increasingly difficult to overcome.
He wants certainty and reassurance. She gradually discovers that she wants a life beyond the relationship.
Keaton's performance is particularly important. Annie feels like a real person rather than a character who exists simply to respond to Alvy's anxieties.
Her independence gives the film much of its emotional weight.
Released in 1977, Annie Hall won Academy Awards for Best Picture, Best Director, Best Original Screenplay and Best Actress for Keaton.
Nearly fifty years later, it remains funny, inventive and surprisingly moving.
Beneath the jokes, there's a genuine sadness.
For a newcomer, Annie Hall offers an introduction to Allen's dialogue, his fascination with relationships and his willingness to experiment with storytelling.
1979 · Manhattan
New York has rarely looked this beautiful.
I should admit something before going any further: Manhattan is my favourite Woody Allen film.
I've watched it countless times, and I still find something new to appreciate, whether it's a line of dialogue, a small expression or another detail in Gordon Willis's extraordinary cinematography.
The opening alone makes a compelling case for watching it.
As George Gershwin's Rhapsody in Blue plays, Allen presents a succession of beautiful black-and-white images of New York City.
Isaac Davis, a television comedy writer played by Allen, attempts to find the right words to describe his relationship with the city.
He keeps changing his mind. The narration becomes increasingly self-conscious, until the music takes over and New York speaks for itself.
It's one of my favourite openings in cinema.
The story follows Isaac's complicated romantic life, particularly his relationships with Tracy (Mariel Hemingway), Mary (Diane Keaton) and his friend Yale (Michael Murphy).
These are flawed, frequently self-absorbed people who spend an extraordinary amount of time discussing their feelings while struggling to understand them.
Allen finds considerable humour in their contradictions, although Manhattan is also among his more melancholy films.
Willis's cinematography gives New York an almost dreamlike quality.
Central Park, the streets of Manhattan and the city's familiar landmarks become part of the film's emotional character.
The music is equally important. Gershwin's compositions lend the film a romanticism that sometimes contrasts sharply with the behaviour of its characters.
And then there's the ending, one of Allen's most affecting, which finds Isaac confronting the limitations of his own outlook.
The music takes over and New York speaks for itself.
Manhattan demonstrates Allen's visual ambition and his ability to combine comedy, romance and disappointment.
If you're interested in cinematography, music or New York on film, this would be my recommendation.
1986 · Hannah and Her Sisters
Almost everyone deserves a story of their own.
For anyone wondering whether Allen can create convincing characters beyond the familiar anxious intellectuals of his earlier films, Hannah and Her Sisters provides an excellent answer.
Set over two years and structured around three Thanksgiving gatherings, the film follows the interconnected lives of Hannah (Mia Farrow), her sisters Lee (Barbara Hershey) and Holly (Dianne Wiest), and the various people involved in their relationships.
Michael Caine plays Elliot, Hannah's husband, whose attraction to Lee threatens to disrupt the family's apparent stability.
Meanwhile, Holly struggles with her career, her relationships and her feelings of inadequacy when compared with her seemingly successful sister.
Allen himself plays Mickey Sachs, Hannah's former husband, a television producer whose fear of death leads him into an increasingly desperate search for religious certainty.
What makes the film work so beautifully is the balance between these stories.
Allen moves from comedy to drama without making the transitions feel forced.
One moment we're watching Mickey's increasingly absurd attempts to find spiritual comfort; the next, we're confronting Elliot's selfishness or Holly's painful insecurity.
The performances are exceptional.
Dianne Wiest brings vulnerability and wonderful comic timing to Holly, while Michael Caine makes Elliot's behaviour understandable without excusing it.
The film's New York setting, its use of classical music and its interest in art and literature are all recognisably Allen.
Yet the writing feels broader and more generous than in some of his earlier work.
There are moments of real warmth here, alongside the usual disappointments and anxieties.
Hannah and Her Sisters received seven Academy Award nominations and won three, including Best Original Screenplay for Allen and supporting acting awards for Caine and Wiest.
It's one of those rare ensemble films in which almost every character feels worthy of a story of their own.
Almost every character feels worthy of a story of their own.
For anyone who enjoys character-driven drama, this is probably Allen's most accessible ensemble film.
It's funny, intelligent, compassionate and full of recognisably human weaknesses.
1989 · Crimes and Misdemeanors
What happens when doing wrong has no consequences?
After the romance of Manhattan and the warmth of Hannah and Her Sisters, it's time to discover a considerably darker side of Allen's filmmaking.
Crimes and Misdemeanors is one of his most ambitious films, examining guilt, morality, religion and the uncomfortable possibility that the world operates without any dependable form of justice.
Martin Landau plays Judah Rosenthal, a wealthy ophthalmologist whose comfortable existence is threatened when his mistress, Dolores (Anjelica Huston), threatens to reveal their affair.
In a parallel story, Allen plays Cliff Stern, an unsuccessful documentary filmmaker whose professional and romantic frustrations provide a more recognisably comic counterpoint.
At first, the two stories seem almost unrelated.
Gradually, their shared concerns become apparent. Both men want life to follow certain rules. Both discover that reality is considerably less obliging.
Allen had explored philosophical questions in earlier films, but Crimes and Misdemeanors addresses them with unusual seriousness.
Judah's religious upbringing shapes his understanding of right and wrong.
His memories of family discussions about faith and morality raise questions that the film refuses to answer comfortably.
The influence of European filmmakers, particularly Ingmar Bergman, is evident, although Allen's combination of comedy and moral uncertainty gives the material its own character.
Landau delivers one of the finest performances in any Allen film, allowing us to see Judah's fear, rationalisations and gradual changes in perspective.
The film also demonstrates something newcomers may not expect: Allen's willingness to leave an audience deeply unsettled.
There's no easy reassurance here.
Both men want life to follow certain rules. Both discover that reality is considerably less obliging.
Crimes and Misdemeanors reveals the philosophical seriousness behind Allen's comedy and introduces themes he would revisit in Match Point, Cassandra's Dream and Coup de Chance.
If you prefer darker, morally complicated stories, this is where I'd begin.
For a first viewing, I'd avoid reading too much about the ending.
2011 · Midnight in Paris
We imagine the past was a better place.
If someone told me they weren't particularly interested in Woody Allen films but loved Paris, literature or art, this is probably the film I'd recommend first.
Midnight in Paris is one of Allen's most accessible and enjoyable later works.
Owen Wilson plays Gil Pender, a successful Hollywood screenwriter visiting Paris with his fiancée, Inez (Rachel McAdams).
Gil dreams of becoming a serious novelist and is captivated by the city's artistic past, particularly the Paris of the 1920s.
One evening, wandering through the streets alone, he finds himself transported back in time, where he encounters some of the writers and artists he has spent years admiring.
F. Scott Fitzgerald, Ernest Hemingway, Gertrude Stein and Salvador Dalí are among the historical figures who appear.
Allen has always been fascinated by nostalgia, and Midnight in Paris gives that fascination an unusually playful expression.
Gil believes he would have been happier living in another period, surrounded by the cultural figures he idolises.
But as the story develops, Allen gently questions whether the past was ever quite as wonderful as people imagine.
It's a particularly appealing idea for anyone who has found themselves wishing they could experience Paris, New York or another beloved city in an earlier era.
Wilson is ideally cast.
His relaxed, slightly bewildered performance gives the film a different rhythm from Allen's more anxious screen characters.
He makes Gil sympathetic without turning him into a straightforward imitation of Allen himself.
Paris looks magnificent, particularly during the film's opening montage, accompanied by Sidney Bechet's recording of Si tu vois ma mère.
And while the film is considerably lighter than Crimes and Misdemeanors, it still asks a recognisably Allen question: why are people so convinced that happiness exists somewhere other than the lives they're actually living?
Midnight in Paris became Allen's biggest commercial success and won the Academy Award for Best Original Screenplay.
Why are people so convinced that happiness exists somewhere other than the lives they're actually living?
It's charming, funny and easy to enjoy without any previous knowledge of Allen's work.
It also provides an introduction to his fascination with art, literature, nostalgia and the passage of time.
Of these five films, it's probably the easiest recommendation to make to someone who has never watched Woody Allen before.
Where to begin
Five films.
No wrong
starting point.
Watching these five films reveals how difficult it is to reduce Woody Allen's cinema to a single style or subject.
Annie Hall breaks the conventions of romantic comedy. Manhattan celebrates the beauty of New York while exposing the shortcomings of its inhabitants.
Hannah and Her Sisters finds humour and humanity in the complications of family life.
Then Crimes and Misdemeanors asks whether morality has any meaning in a world where wrongdoing can go unpunished.
And Midnight in Paris reminds us that Allen can still find considerable pleasure in romance, imagination and the absurdities of human behaviour.
They also demonstrate how his filmmaking changed over time.
The formal experimentation of the 1970s gradually gave way to more intricate ensemble dramas, darker moral questions and, later, stories set far beyond the New York neighbourhoods most closely associated with his work.
Of course, five films barely scratch the surface.
Anyone who enjoys Allen's early humour should seek out Bananas, Sleeper and Love and Death.
Those interested in his more serious work might prefer Interiors, Another Woman or Husbands and Wives.
And if you enjoy the theatrical humour of Hannah and Her Sisters, there's plenty more to discover in Bullets Over Broadway and Radio Days.
My personal recommendation would be to watch these five films in their release order.
Begin with Annie Hall and finish with Midnight in Paris.
You'll travel from 1970s New York to the Paris of the 1920s, meeting some extraordinary characters along the way.
And if one of these films captures your imagination, follow that particular direction rather than feeling obliged to watch everything chronologically.
There's no correct way to discover Woody Allen's cinema.
For me, the pleasure has always been finding something unexpected, even in films I've watched many times before.
And if you eventually decide that Manhattan is his finest film, you'll get no argument from me.