The Best & The Rest: Every Woody Allen Film Ranked

10. “Sleeper” (1973)
Of all the people to be unfrozen 200 years in the future by the rebel underground, scientists unearth the pod containing neurotic jazz-musician/health-store owner Miles Monroe (Allen). With the country ruled by a despot, Miles must infiltrate the government’s uber-secret “Ares Project,” with the help of reluctant hippie poet Luna (Diane Keaton), who eventually turns to the underground cause. Parodying every popular sci-fi trope of the time (a very HAL-like all-seeing computer, for example) and pulling heavily from the works of Buster Keaton and Charlie Chaplin (especially in the robot butler sequence) “Sleeper” is utterly charming fun, that also makes time for a little social critique, like the impermanence of scientific “fact” (a dialogue between two people reveals that fatty, greasy foods and cigarettes are actually extremely healthy) and the modern world’s erosion of intimacy (the brilliant “Orgasmatron”). But though it’s surprisingly trenchant in some of its observations, in the main, it’s blissfully silly fun, building to a cloning scene which might be the most joyous example of extended Keaton/Allen chemistry and tomfoolery he ever filmed.

9. “Sweet and Lowdown” (1999)
Though Allen has missed the mark as often as he’s hit it in his mid-to-later periods, this film is a shining example of everything the writer/director can do right when he’s firing on all cylinders. He gets revelatory, surprising, Oscar-nominated performances out of Sean Penn, as narcissistic fictional guitar player Emmet Ray (transparently based on the legendary Django Reinhardt), and Samantha Morton as mute, adorable Hattie, Emmet’s lover. He uses a faux documentary style, despite the authentic and textured period details, to augment the grandeur of Ray’s life and artistry, with smart dialogue that is quippy and fun highlighting one of the best scripts he’s ever written in terms of balancing dramatic and comedic moments. Moreover, Allen is a lifelong lover and performer of jazz, and this is one of his biggest love letters to the tunes, myths and larger-than-life personalities that populate the genre. As such it is as fundamental to Allen’s personal filmmaking style as the New York City of “Manhattan” or the May-December romance of “[insert title here.]”

8. “Crimes and Misdemeanors” (1989)
“I remember my father telling me, ‘The eyes of God are on us always.’ The eyes of God… And I wonder if it was just a coincidence I made my specialty ophthalmology.” So says Judah Rosenthal (Martin Landau, in a late career-high) in Allen’s bleakly funny rumination on the nature of justice, divine and otherwise. For Judah, an affair with Dolores (Anjelica Huston) has turned potentially ruinous, and the means by which he plans to remove Dolores will force Judah to come face to face with his inner darkness in no uncertain terms. Allen himself provides the lighter B-plot as Cliff, a failed filmmaker tasked with covering the every-day exploits of pompous producer Lester (Alan Alda). While the film features some choice zingers (like Lester’s proud observation “If it bends, it’s funny. If it breaks, it isn’t”), Judah’s plotline is foregrounded and features some of the best character writing Allen’s ever done. Shot by Bergman collaborator and cinematography giant Sven Nykvist, ‘Crimes’ features scenes not just of dry humor and wit, but of startling beauty and great sorrow — an elegant film about most inelegant people.

7. “Interiors” (1978)
One of the boldest reactionary moves in cinema — following up the beloved and Academy Award, Best Picture-winning “Annie Hall” with an icy chamber drama — Woody Allen’s still undervalued and heavily Ingmar-Bergman-indebted “Interiors” is masterwork of meticulously crafted mise en scene that deepens the already claustrophobic mood and sense of emotional distance. Gordon Willis’ stellar compositions and pale illuminations are perhaps his most underrated work as well. Centering on a fragmented trio of neurotic sisters (Diane Keaton, Mary Beth Hurt and Kristin Griffith), their lives are upended when their seemingly content parents unexpectedly divorce. The sudden ending to the household unearths unhealed wounds, manic distress and painful resents that places the family on the edge of disintegration. As the title heavily implies “Interiors” is all about the intimate inner lives of its characters that reflect, often quite devastatingly, on the past, their upbringing and their family. Post Oscar win, Allen had chips to cash and he doubled down on a emotionally shattering that’s tragic, devastating in its bleak conclusion and, given the protests that greeted its top 10 placement here, probably the director’s most underrated film.

6. “Bullets Over Broadway” (1994)
One of the rare occasions on which the director shares a screenwriting credit (a one-off collaboration with Douglas McGrath) “Bullets over Broadway” is Allen at his best, with 7 Oscar nominations to prove it. The film marked one of his purest, most unalloyed joys since the “early, funny ones” as if Allen himself had suddenly grown tired of the wider existential moroseness that had marked many of his preceding titles. Despite in many ways being the least Woody-like of the proxies, John Cusack is fantastic (one of his best roles) as the 1920s Barton Fink-ish playwright with delusions of Eugene O’Neill greatness, and the rest of the cast play a delicious horror show collection of freaks, pedants and oddballs. Jennifer Tilly is wondrous as the screeching, dunderheaded moll Olive who doesn’t understand the word “fore” (“So you’re telling me I’m talking about golf?”) and Dianne Wiest, of course, is killer in an Oscar-winning performance as the vainglorious Helen Sinclair, who seduces Cusack by lustily breathing, “Don’t speak!” and “The world will open up to you like a magnificent vagina!” like Gloria Swanson off her face on prescription drugs.

5. “Love and Death” (1975)
Allen’s career to this point has been a series of movies that were little more than sketch shows: knockabout gags elevated by his erudition and intellectualism. But in “Love and Death” we see his more scattered tendencies take shape, yet without losing the anarchic energy of his scrappier work. The shaggy-dog story of a loner who screws up so badly he can’t even die right, Allen plays a Russian coward named Boris whose love for Sonja (Diane Keaton) vies with their political disagreements as Napoleon’s army advances. Featuring then-trademark knockabout slapstick and crude sex gags (on being congratulated on being a powerful lover Boris replies “thanks, I practise a lot when I’m alone”) it is nonetheless also one of Allen’s more conceptual pictures, dense in allusions to the tragic romances and epic existentialist novels of Tolstoy and Dostoyevsky. And there’s an infectious, impish glee on display too, as though Allen can’t quite believe his luck that he gets to treat the great works of classic literature (and indeed filmmaking) as his own personal sandpit.

4. “Husbands and Wives” (1992)
Marriage is seldom a “happily ever after” — more likely it’s just the “after,” as Allen’s usual cast of Upper East Side neurotics discover in this tremendously acerbic dramedy which hews somewhat closer to the dramatic end of the spectrum. Gabe and Judy (Woody Allen and Mia Farrow), are the married best friends of couple Jack and Sally (Sydney Pollack and Judy Davis) who decide to separate, sending Gabe and Judy into a tailspin of their own. Gabe is attracted to a precocious student (Juliette Lewis) and Judy develops feelings for a man in her office (Liam Neeson). The ensemble all perform brilliantly, in particular a show-stopping Davis, as the uber-neurotic Sally (she was Oscar nominated, as was Allen for Screenplay). Aesthetically, the film feels unadorned, even quasi-documentary, which proves an inspired choice in keeping these often ugly characters grounded in reality and in contributing to the overall sense of energy and momentum that makes an ironic film about decaying relationships and the perils of taking each other for granted feel like it zips past in dust cloud of snappish dialogue and withering insight.

3. “Hannah and Her Sisters” (1986)
Borrowing the loose, holiday-centered structure from Ingmar Bergman’s “Fanny And Alexander” (except with Thanksgiving instead of Christmas) Allen’s tale of the loving yet complicated relationship between three sisters is one of the finest films of the 1980s and certainly one of the best films of his career. Hannah (Mia Farrow) has two sisters, the flighty Lee (Barbara Hershey) and the nervy Holly (a career-best Dianne Wiest). The former bounces from a relationship with intense Frederick (Max Von Sydow) to an affair with Hannah’s husband, while the latter struggles simply to find her place in life. Both tender and hilarious, Allen captures the foibles and follies of middle age but even makes time for a digression about the architectural wonders of the city that is right up there with the opening of “Manhattan,” as a poignant postcards to his native city, shot gorgeously by Carlo Di Palma. “For all my education, accomplishments and so-called wisdom, I can’t fathom my own heart,” says Hannah’s husband Elliot (a terrific Michael Caine) and it serves as a perfect encapsulation of the film’s wise, witty but eternally wondering core.

2. “Manhattan” (1979)
“Annie Hall” is his most beloved film, but it’s “Manhattan” that is undoubtedly Allen’s most visually iconic: with the indelible pairing of that lazy wail from the beginning of Gershwin‘s “Rhapsody in Blue” over black-and-white shots of the classic New York skyline, it doesn’t just encapsulate the essence of Allen, it defines the image of his beloved home city in the collective cinematic imagination. This time, in various overlapping tragicomic storylines, Isaac (Allen) pursues 17-year-old Tracy (Mariel Hemingway), while close friend Yale (Michael Murphy) cheats on his wife with Mary (Diane Keaton). Allen’s writing here is typically sharp and his musings on “Why is life worth living?” is a darling moment for the typically dour auteur. But what stands out above all else is a picture of the Big Apple, and the idea of the city itself as a force that can shape, console and rejuvenate you. “Manhattan” embodies many of the narrative tendencies that Allen would display going forward — for better or worse — and is as funny/sad as anything he’s done, but it’s also perhaps the very fondest film ever made about a person’s relationship to the place they live.

1. “Annie Hall” (1977)
The film that bridges the so-called early funny ones with the more serious later work that would come, “Annie Hall” is also easily Allen’s most autobiographical film up to that point (and possibly ever) and it landed four major Oscars — Best Actress (Diane Keaton), Best Director, Best Screenplay and Best Picture. But you know all this — it’s perhaps his most beloved film, named constantly by filmmakers as the Platonic form of the romantic comedy that all others aspire to. And that’s because it’s terrific; insightful, playful, moving and beautifully acted, particularly by Keaton, who essentially creates the manic pixie dream girl archetype here, but has it spring from so deep within that it feels truthful for the first and maybe only time ever. She’s so era-definingly strong, in fact, that the somewhat mean-spirited portrayals of Alvy’s other women (Shelley Duvall and Carol Kane), pale into insignificance. Perhaps not a surprising choice of number 1, but an inevitable one, “Annie Hall” remains one of the apotheoses of cinematic romance because with lacerating wit and an ocean of self-awareness, it describes every moment of a love affair, from dazzle to disillusion, between characters so awkward and hopeful and real that you feel like you’ve lived it yourself. Lah-di-dah.

— with The Playlist Staff