Okay, let's talk Woody Allen. I know, I know – the guy's personal life is a minefield. But here's the thing: whether you love him or hate him, his filmography is like a masterclass in neurotic storytelling. People keep searching for the best Woody Allen movies because they want that perfect blend of wit, jazz, and existential dread. And honestly? When he's on his game, nobody does it better.
I remember watching "Annie Hall" for the first time in college. My roommate said, "You look like you're having a religious experience." Maybe I was. That scene where Alvy recalls his childhood under the rollercoaster? Pure magic. But then you get something like "Wonder Wheel" years later and... oof. More on that later.
This isn't just some random ranking. I've sat through all 50-ish of his films (yes, even "September"). We're going beyond IMDb scores to dig into what actually makes a Woody Allen movie stand the test of time. Expect specifics: why certain scenes work, where to stream them, even which performances fell flat. Because when you Google "best Woody Allen films," you deserve more than a bland list.
What Makes the Greatest Woody Allen Movies Tick?
Look, ranking art is messy. But after analyzing his work since the 70s, three elements consistently separate the masterpieces from the misfires:
| Factor | Why It Matters | Perfect Example |
|---|---|---|
| The Writing | Those rapid-fire monologues about death and sex and why bagels make life worth living? That's Allen's signature. Weak scripts drown in their own cleverness. | "Manhattan" - The opening narration alone is poetry |
| Cinematic Vision | Early Allen was all talk. But when he started caring about visuals? Gordon Willis' black-and-white NYC in "Manhattan" or the Venetian light in "Everyone Says I Love You" changed everything. | "Midnight in Paris" - Gil walking into the 1920s is pure cinema |
| Performances | Allen's an actor whisperer. When he casts right (Cate Blanchett in "Blue Jasmine"), it's revelatory. When he doesn't ("Café Society" pretty boy Jesse Eisenberg), it derails scenes. | "Hannah and Her Sisters" - Dianne Wiest's nervous Oscar speech steals the film |
Personal beef: I think Allen underuses cinematography sometimes. His early films feel like filmed stage plays. But when he collaborates with great DP’s? Game changer. Santo Loquasto's production design in "Radio Days" makes me nostalgic for a Brooklyn I never knew.
The Definitive Best Woody Allen Movies Ranking
Let's get granular. These aren't just "good" – they're essential viewing. Streaming info updated July 2024 because nothing's worse than dead links.
| Movie Title | Year | Key Cast | Runtime | Where to Stream | Why It's Top Tier |
|---|---|---|---|---|---|
| Annie Hall | 1977 | Woody Allen, Diane Keaton | 93 min | Amazon Prime, Apple TV | Invented modern romantic comedy. Broke 4th walls before it was cool. Keaton's fashion started trends. |
| Manhattan | 1979 | Woody Allen, Diane Keaton, Meryl Streep | 96 min | Hulu, Paramount+ | Gordon Willis' B&W photography makes NYC a character. That bridge scene at dawn? Iconic. |
| Hannah and Her Sisters | 1986 | Mia Farrow, Dianne Wiest, Michael Caine | 107 min | Max, Apple TV | Perfect ensemble storytelling. Caine's affair plot feels painfully real. Wiest won a deserved Oscar. |
| Midnight in Paris | 2011 | Owen Wilson, Marion Cotillard | 94 min | Netflix, Prime Video | Proves Allen still had magic late-career. Hemingway parody is genius. Makes you book Paris flights. |
| Crimes and Misdemeanors | 1989 | Martin Landau, Anjelica Huston | 104 min | Criterion Channel | Darkest Allen ever got. Landau's moral collapse is terrifying. That final party scene haunts me. |
Annie Hall - Why It Still Works
That lobster scene. You know the one. Allen and Keaton fumbling in the kitchen – it’s the most relatable relationship moment ever filmed. But here’s what people miss: the editing. Allen cuts mid-sentence constantly, mimicking how memory works. Most romantic comedies steal from this but forget the existential angst underpinning it.
Personal confession? I think Diane Keaton carries this film. Allen’s Alvy is funny but insufferable. Keaton makes Annie charming despite her quirks. Without her, it’s just 90 minutes of whining.
Manhattan - More Than Postcards
Yes, the skyline shots are gorgeous. But watch how Allen frames dialogue: characters cramped in tiny apartments, talking over each other while taxis blur outside. It visualizes urban claustrophobia. Also – controversial take – Mariel Hemingway’s Tracy is the only sympathetic character. Allen’s Isaac dating a 17-year-old? Creepy even in 1979.
Real talk: Allen’s May-December romances age poorly. "Manhattan" skirts the line, but "A Midsummer Night’s Sex Comedy" with a 62-year-old Allen lusting after Mia Farrow at 37? Uncomfortable. It’s why some of his best movies get overshadowed.
The Midnight in Paris Surprise
Nobody saw this coming. After a decade of forgettable films, Allen drops this love letter to nostalgia. Owen Wilson nails the Allen persona without imitating him. Corey Stoll’s Hemingway (“Who wants to fight?”) steals every scene. And Gil’s realization that every era romanticizes the past? That’s Allen’s wisest observation since "Annie Hall".
Fun fact: The time-travel scenes cost less than $100k. Allen shot them guerilla-style at 3 AM near Pont Alexandre III. That’s filmmaking economy.
Overlooked Gems You Can't Miss
Everyone talks about the classics. These underrated picks deserve streaming tonight:
- Radio Days (1987) - Pure nostalgia. No neurosis, just young Joe’s memories of 1940s Queens. Diane Wiest as the tipsy aunt is perfection.
- Sweet and Lowdown (1999) - Sean Penn as fictional jazz guitarist Emmet Ray. His panic attack after seeing Django Reinhardt play? Heartbreaking.
- Broadway Danny Rose (1984) - Allen’s most humane performance. A hapless talent manager caring for a client’s mistress. The Thanksgiving scene kills me.
Weirdly, "Zelig" (1983) holds up. That fake documentary style predated "Borat" by decades. The technical wizardry inserting Woody into historical footage? Mind-blowing for its time.
Movies That Don't Deserve the Hype
Critics aren’t always right. These made "best Woody Allen movies" lists but flop today:
- Match Point (2005) - Hailed as a comeback. Sorry, but Jonathan Rhys Meyers’ “acting” consists of scowling. The moral dilemma? Thin.
- Vicky Cristina Barcelona (2008) - Penélope Cruz won an Oscar, but the male gaze on Scarlett Johansson feels icky now. Also, Javier Bardem’s artist is a pretentious bore.
- Wonder Wheel (2017) - Kate Winslet tries hard, but the dialogue sounds like Allen parodying himself. Jim Belushi? Miscast disaster.
Full rant: Why does "Interiors" (1978) get called “profound”? It’s Bergman-lite with worse sweaters. Maureen Stapleton’s earthy Pearl saves it, but barely. Allen doing straight drama without irony is like decaf coffee – pointless.
Where to Start Based on Your Mood
Overwhelmed? Match your vibe:
| You Feel Like... | Watch This | Skip If... |
|---|---|---|
| Laughing at relationships | Annie Hall, Manhattan | You hate people complaining |
| Philosophical debates | Crimes and Misdemeanors, Hannah and Her Sisters | You want clear answers |
| Pure escapism | Midnight in Paris, Radio Days | You dislike fantasy |
The Elephant in the Room
Can we separate art from artist? Look, I struggle with it. When Dylan Farrow’s op-eds resurface, I question rewatching "Husbands and Wives". Many film buffs have stopped watching his work entirely – totally valid.
But here’s my messy take: Cinema history is full of problematic figures. Polanski. Hitchcock. Do we burn "Chinatown" and "Vertigo"? Art’s legacy gets complicated. I won’t judge anyone who avoids Allen’s movies. Yet dismissing them entirely erases contributions from hundreds of collaborators – Gordon Willis, Dianne Wiest, Carlo Di Palma. It’s a personal call.
Essential Woody Allen FAQ
Let's tackle those recurring searches:
Which Woody Allen films actually hold up well today?
The universal ones: "Annie Hall" (relationships stay messy), "Crimes and Misdemeanors" (morality’s timeless), and "Radio Days" (nostalgia transcends eras). Avoid "Everything You Always Wanted to Know About Sex" – the humor’s painfully dated.
Why do critics obsess over Manhattan?
It’s Exhibit A for Allen’s visual growth. Before this, his movies looked like TV sitcoms. The widescreen B&W cinematography forced him to think cinematically. Also – that Gershwin soundtrack.
Where can I stream his best work legally?
It rotates. As of 2024: Prime Video has the United Artists classics ("Annie Hall", "Manhattan"). Criterion Channel hosts his 80s-90s gems. Netflix occasionally licenses "Midnight in Paris".
What’s Woody Allen’s funniest film?
"Sleeper" (1973). Fight me. The lobotomy scene? The orgasmatron? Pure slapstick genius. Allen stopped doing physical comedy too soon.
Are his European phase films worth watching?
Mixed bag. "Match Point" is overrated. But "Vicky Cristina Barcelona" has Cruz’s fiery performance, and "Blue Jasmine" is top-tier Cate Blanchett. Skip "To Rome With Love" – even Italians hated it.
Final Takeaways
Look, debating the best Woody Allen movies is half the fun. My list will annoy purists ("Where's 'Purple Rose of Cairo'?!"), but that’s cinema. His peaks reshaped comedy, romance, and how we talk about death in films. His lows? Weird misfires about psychic detectives ("The Curse of the Jade Scorpion").
If you watch nothing else, see "Annie Hall" and "Crimes and Misdemeanors". One captures love’s chaos, the other stares into the moral void. Both prove why Allen mattered – personal demons aside. Just maybe skip anything post-2013. Trust me.
What’s your controversial Allen take? Email me. I once got a 3-page rant about "September". People feel things.