An achingly gorgeous love letter to New York, this is one of the greatest romantic comedies of all time. Gershwin’s Rhapsody in Blue underscores the love and the heartbreak, while Gordon Willis’ beautifully black-and-white camerawork is the icing on the cake. It’s witty, mournful and clever, sometimes simultaneously.
2. Annie Hall
No film ever suited Diane Keaton better. In the title role, she’s sublime – ditzy, funny and utterly endearing. Another love letter from Allen – but this time to his leading lady. He never wrote sharper dialogue, and the one-liners keep coming thick and fast. A delicious entertainment.
3. Hannah and her Sisters
This terrifically assured piece ensemble piece, about love, betrayal and intermingling relationships within a Manhattan family, confirmed Allen as a brilliant director of actors. Mia Farrow, Dianne Wiest and Barbara Hershey all gave stellar performances – and Michael Caine too was a revelation.
4. Purple Rose of Cairo
Cinema itself is the object of Allen’s affection in this sweet-natured, poignant story with Mia Farrow as a movie-crazed waitress who wins the heart of a film star; he steps out of the big screen into real life to woo her. It’s an ingenious idea, executed with wit and panache.
5. Crimes and Misdemeanors
This was Allen’s ambitious attempt to bring serious moral themes into his films, right alongside his brilliant gags. Martin Landau plays a surgeon, tempted to have a hit-man dispose of his mistress, who is threatening to expose him to his wife. Comedy and tragedy occupy equal space in this fine drama.
6. Blue Jasmine
Easily the finest Allen work of recent years, with Cate Blanchett imperious in her Oscar-winning title role as a New York socialite down on her luck and out of money, who descends on her poorer sister’s humble West Coast home. This ranks among Woody’s best-written and directed films.
7. Broadway Danny Rose
Mia Farrow again, as a gangster’s moll paired with Allen’s hapless small-time showbiz agent, who falls foul of the Mafia. She’s terrific, but the setting is truly rich – a world of corny gags, ageing entertainers and the desperation among those who never rose above the bottom of the bill.
8. Bullets Over Broadway
Hilarious, dazzling, brilliantly executed caper with John Cusack as a struggling dramatist whose new play is financed by a Mob boss with one proviso – he wants his talentless girl-friend to be the leading lady. It moves at a breakneck pace, and it’s delicious fun.
9. Midnight in Paris
This was Allen’s biggest box-office hit in years – a delightful frothy fantasia of a movie about a screenwriter (Owen Wilson) visiting France with his fiancée’s family, but finding himself magically whisked back to the gaiety of the 1920s each night.
10. Radio Days
A strongly autobiographical piece, shaped by Allen’s childhood in the 1940s, his raucous family – and the unifying effect of a radio set in the house. Warm sepia tones prevail, and a specific moment in time is lovingly re-created. It’s underrated within Allen’s canon, but very worthwhile.