Woody Allen Movies, Ranked From Best to Worst

Allen’s bittersweet romantic comedy, inspired by his real-life romance with Diane Keaton, is his most complete and completely satisfying film. Adjusted for inflation, it’s his biggest hit to date. For apprentice filmmakers, it’s a master class in technique (Allen uses every trick in his arsenal, including split-screens, subtitles, and animation), editing, story structure, and, of course, dialogue. It has some of Allen’s best visual and verbal gags. It’s the model for virtually every smart, urbane romantic comedy of the last 36 years. And it features Keaton at her most luminous, in the role for which she’ll be best remembered. What’s not to like?

Allen’s warm and generous dramedy about three very different sisters contains multitudes. Among other things, it’s a tribute to Allen’s on- and off-screen partner Mia Farrow (she and her mother and several of her children are cast members), a twisty romantic comedy, an Oscar-winning showcase for Michael Caine and Dianne Wiest (in her star-making role), and a comic epic about a spiritually bereft man’s search for meaning. Allen’s monologue near the end of the movie — his recognition, via a viewing of the Marx brothers’ “Duck Soup,” that, even if we live in a godless universe and go around just once, we can still find joy and meaning in art and in love — is the very heart of all of Allen’s body of work.

This is the ideal fusion of Allen’s light-and-funny movies and his dark-and-serious ones. A drama (featuring Martin Landau, in his finest performance) and a comedy (featuring Allen and Farrow) play out in parallel storylines that intersect only at the end of the film and reinforce the point that we live in a universe without justice, where the good often suffer and evil often goes unpunished, even rewarded. It’s the flip side of the message of “Hannah and Her Sisters,” along with a reminder that what meaning we can find in such a universe comes from the ties we forge with other people.

The most bittersweet of Allen’s romantic comedies, and the most gorgeous-looking (thanks to Gordon Willis’s striking black-and-white shots of New York). It’s a film of goodbyes; this is his last film with Keaton as star/muse (at least for the next 14 years) and his last film of the 1970s. Not to mention the disastrous ways that romances end in the movie. (Given Allen’s personal history, the romance between his character and teenage Mariel Hemingway is kinda creepy, but she turns out to be smarter than he is.) In the end, Allen can depend only on his beloved city, and for anyone who’s ever fallen in love with New York, that may be enough.

Allen makes the same point, as in “Crimes and Misdemeanors,” about the universe being a place without justice, using a similar tale of a man who murders an inconvenient woman in order to preserve his marriage and social status. But this time, he does so without the consolation of comedy. The result is as chilling, bracing, and pure as a swim in Arctic waters. The icy-cool/steamy-hot coupling of sociopathic social climber Jonathan Rhys Meyers and temptress Scarlett Johansson is a highlight of Allen’s first movie filmed in London, marking the beginning of his recent salutary run of movies set in Europe.

Sexual adventuring is not for the faint of heart, as Rebecca Hall learns in this comedy of manners. Hall is one corner of a romantic quadrangle (along with Johansson, Javier Bardem, and Oscar-winning scene-stealer Penelope Cruz) in which two American women get more than they bargained for when they tap into the lusty vida loca lived by artists in Spain. Again, the change of venue does Allen good; like Hall, he seems both terrified and delighted to discover a tempestuous stew of sex and culture so far from provincial Manhattan.

The funniest, most broadly slapstick film of Allen’s early comic period, “Sleeper” is also a surprisingly sly sci-fi satire, with a cryogenically frozen Allen waking up two centuries from now to find himself in an Orwellian society that’s literally led by the nose. The usually cerebral writer/director/star doesn’t get enough credit for his prowess as a physical comedian, but gags here involving a giant reel of recording tape, a jet pack, and robot butlers should remind you how funny he can be without saying a word.

Allen plays a sad-sack talent agent to an ad hoc family of pathetically talentless performers in this comic meditation on showbiz nostalgia, the virtues and limits of loyalty, and the differences between Italians and Jews. Shot in timeless black-and-white, the film contains a crackling performance by Farrow, against type, as a big-haired Jersey girl, as well as a priceless comic sequence involving the Macy’s parade balloons.

After dumping longtime girlfriend Farrow for her adopted daughter — and being roundly condemned as a cad at best and pedophile at worst — Allen made a series of movies that, while hardly apologies, were explorations of the idea that it’s possible to be both a great artist and a terrible human being. This was the first of those movies, and it’s also the funniest. John Cusack (as a pretentious playwright), Chazz Palminteri (as a better playwright, who’s also a mob hitman), Dianne Wiest (in another Oscar-winning turn, as a Broadway diva), and a pitch-perfect supporting cast turn this bitter cocktail into a fizzy concoction.

The highest-grossing movie of Allen’s career (not adjusting for inflation) is this recent smash that proves nostalgia ain’t what it used to be. Restless screenwriter Owen Wilson gets his wish, every night, to be transported back to 1920s Paris, rubbing shoulders with Picasso, Hemingway, Fitzgerald, Stein, and other legends, only to discover that each era has its discontents and regards a previous time as a lost golden age. You don’t have to get all the references and in-jokes (the best of which is Corey Stoll’s ultra-confident Hemingway) to appreciate the travelogue, the wistful thinking, or the lesson that the true golden age is always right now.

A dozen years before computer graphics made it possible to insert Tom Hanks into historical footage in “Forrest Gump,” Allen did it by hand (and in black-and-white) in this clever mockumentary about a human chameleon (Allen) who assimilates with eerie ease into the realm of the rich and famous. The movie is prescient, too, in regarding Zelig’s yen for fame (or at least proximity to it) as a modern kind of mental illness.

Here’s another sharp, edgy, artist-as-cad movie, this one filtered through the plot of Bergman’s “Wild Strawberries” and the sensibility of Philip Roth. As a result, it’s Allen’s most profane, coruscating work. Allen raids his own subconscious for praise and condemnation, raids his bag of cinematic tricks for visual and conceptual gags, and takes a brief tour of hell (Billy Crystal is Satan). He proves he’ll do anything for a laugh, no matter whom he hurts, including himself.

In a conceit borrowed from Buster Keaton’s “Sherlock Jr.,” Jeff Daniels plays Tom Baxter a dashing 1930s movie hero who walks off the screen and into the arms of his most ardent fan, miserable housewife Farrow. Things get complicated when Gil Shepherd, the real-life actor who plays Tom (also Daniels) shows up and falls for her, too. Forced to choose between fantasy and reality, she chooses wrong. “Purple Rose” may be a dark and twisted valentine to the consoling power of movies, but it’s also pretty funny, especially when Tom Baxter start walking out of the picture in screens across America.

Made as his own relationship to Farrow was crumbling, Allen’s last movie with Farrow is a bitter but thoroughly riveting drama about several star-crossed couples. Allen and Farrow are actually the most benign; the most powerful performances belong to Sydney Pollack and Judy Davis as a couple right out of “Who’s Afraid of Virginia Woolf?” Bonus points to Juliette Lewis as a coed who catches Allen’s eye, but who also has his number.

Allen’s directing debut is also one of his funniest movies. His first mockumentary, it’s the story of Virgil Starkwell (Allen), the most inept bank robber of all time. Classic gags abound, including the illegible stick-up note and the gun carved from a bar of soap that turns to foamy bubbles in a rainstorm.

Allen’s general contempt for politics and ideology is apparent throughout this satirical farce, in which he plays a guy who becomes a Latin American revolutionary leader in order to impress a cute radical (real-life ex-wife Louise Lasser). Includes the priceless gags in which sportscaster Howard Cosell covers a political assassination and, later, a marriage consummation.

Who but Allen could get away with a movie making fun of 19th-century Russian novels? Dostoyevsky and Tolstoy take it on their long-bearded chins as Allen plays a reluctant Russian soldier, fighting in the Napoleonic wars and wooing aristocratic women. Not that you need to know the highbrow references to enjoy the film’s sight gags and sex jokes.

Allen didn’t direct this one, but it bears his auteurist stamp. Adapted from his own play, “Sam” features Allen as a movie critic who takes romantic advice from the ghost of Humphrey Bogart (Jerry Lacy). It’s Allen’s first movie with Keaton, and they display eccentric but wonderful chemistry as they form what will be the signature screen couple of the 1970s. It’s also Allen’s first valentine to his own art form, and it’s fun to measure the distance between the romantic ideal of the 1940s that Bogart embodied and the new misfit-as-romantic-lead template Allen was then busy creating for himself.

Allen’s thoroughly charming period piece combines old showbiz gossip with recollections of his own upbringing. How much of it is true and how much is made up or misremembered? It doesn’t really matter. There’s not much of a point, except to remind Allen fans once again of the fantastic and transformative powers of art, especially for an audience living through misery and hardship. Features an impossibly young (and funny) Seth Green as the pubescent Allen surrogate.

Allen’s attempt at a musical (using the pre-1950 jazz and pop chestnuts he loves) is hit or miss, depending on the widely varying singing talents of his all-star cast (Edward Norton and Tim Roth are surprisingly good; Allen himself and Julia Roberts are the worst). As a look at love and romance through the escapades of a rich and wacky New York family (of the kind that probably existed only in 1930s movies), however, it’s a winner. Natasha Lyonne became a star as the boy-crazy teen who serves as a sardonic narrator.

Allen tries to make it up to Tracey Ullman for not giving her a bigger part in “Bullets Over Broadway” by casting her in the lead here as a petty thief’s social-climbing wife. But the movie is stolen by Elaine May, whom Allen coaxed out of retirement to play Ullman’s blissfully dim-witted cousin. The movie starts out looking like a retread of “Big Deal on Madonna Street,” with Allen leading a group of inept, Virgil Starkwell-ish bank robbers, but it soon transforms into a social satire about class and status symbols. Turns out the rich may or may not have better taste than the poor, but they certainly include a more accomplished class of thieves.

Allen’s last film with Keaton (and his first with her in the decade and a half since their 1970s heyday) is a neat little comedy that has the pair playing a longtime couple whose stale marriage perks up when they start sleuthing (they suspect their neighbor of killing his wife). (Those playing Spot The Allusion will catch nods to such classics as “Rear Window,” “The Thin Man,” and “The Lady from Shanghai.”) Anjelica Huston nearly steals the film as a woman of mystery who coaches the couple on how to entrap the alleged killer.

Allen’s conceit of having an ancient-school Greek chorus narrate a modern-day romantic farce is certainly novel but also superfluous. The story of an adoptive dad (Allen) who’s horrified to discover that his brilliant son’s real mom is a hooker/porn actress (Mira Sorvino) is amusing enough on its own. Sorvino’s helium-voiced performance, alternately hilarious and grating, won an Oscar.

The end of Allen’s artist-as-cad series is a mockumentary that features a surprisingly winning performance by Sean Penn as a brilliant but solipsistic 1930s jazz guitarist, along with another surprisingly winning performance by Samantha Morton as his mute love interest. Neither character should work, but they do, through the performers’ sheer Method conviction. Naturally, the score is terrific.

As trifles go, this one’s pretty good. Allen’s second London movie is a farce about a plucky American journalism student (Johansson) who stumbles upon a great tabloid crime story thanks to a tip from a ghost, who sends her messages via a third-rate magician (Allen). In her second movie with Allen, the two make an oddly sweet father/daughter team, though their rhythms are a little off. Hugh Jackman is good, too, as the seductive aristocrat whom Johansson suspects is a serial killer.

Allen’s first truly serious, non-comedic movie is this Bergman-style psychological exploration of a disintegrating family. There are some fine, stark performances here, particularly by Geraldine Page as the matriarch and Keaton and Mary Beth Hurt as two of her daughters, but the whole thing has the oppressive weight of a graduate student’s vain effort, trying to hard to emulate his mentor.

Here’s a Bergman knock-off that’s not heavy at all, since it’s essentially a re-do of the Swedish master’s early sex farce “Smiles of a Summer Night.” Allen’s first movie with new off-screen love Farrow, the whole thing is lighter than air but thoroughly diverting. Jose Ferrer steals the movie as an old fool in love.

Allen’s most recent film (before the forthcoming “Blue Jasmine”) is another lovely travelogue, like its immediate predecessor (“Midnight in Paris”), but without any of that film’s substance. Here, the Eternal City is just another playground for mismatched lovers. The results are pretty funny, but they come with a hefty helping of déjà vu.

Allen’s inventive take on the popular sex-advice book is a series of sketches, all done in different styles, from medieval farce to 1960s Italian cinema to sci-fi/horror flick. Highlights include Gene Wilder as a shrink who falls for a sheep, Lou Jacobi as a cross-dresser, and Allen as a sperm preparing for launch. Oh, and watch out for the monster-sized boob.

Allen’s valentine to Farrow is a weird “Alice in Wonderland”-inspired comedy, one that sees Farrow playing an Upper East Side socialite who reexamines her unfulfilling life under the influence of some magical Chinese herbs. The fantasy sequences are delightful but don’t really fit with the rest of this lugubrious, clichéd narrative. Farrow, whose strength should be at the story’s center, instead seems to get lost in it.

Allen’s version of Fellini’s “8 ½” is widely viewed as a screw-you to his fans, especially those who wish he’d keep making movies like his “early, funny ones.” There’s a little more art than that in this tale of a director (Allen) who’s stuck in a creative and romantic rut. But not much.

In Allen’s third London-set movie, Colin Farrell and Ewan McGregor play brothers seeking a quick score and turn to crime, with disastrous results. It’s not a bad thriller, but it takes a while to get going, and it’s hardly as substantial as “Match Point.” Plus, Allen’s not really the right director for gritty, kitchen-sink naturalism.

Returning to Manhattan after four films in Europe, Allen casts Larry David as his surrogate, an old crank with a young wife. There’s not much more to it than that. David’s funny, as usual, but he’s still pretty much playing the Larry David of “Curb Your Enthusiasm,” and 92 minutes of that guy ranting is more than enough.

Allen returns to London with another farce about smart (and sometimes old) people making foolish romantic choices. Despite a strong cast (Anthony Hopkins, Naomi Watts, Josh Brolin, Antonio Banderas), this one doesn’t really gel.

Allen and Helen Hunt star as two 1940s insurance claims adjusters who fall in love while under the hypnotic influence of a larcenous magician. It’s about as hilarious as it sounds, which is not much. Hunt comes off as too contemporary to play a Rosalind Russell-style wisecracking dame, and she has no chemistry with Allen. Charlize Theron, in a small role as a wealthy bad girl, steals the film.

In this drama, Gena Rowlands plays an author whose emotional reserve shatters when she eavesdrops on the sessions of a depressed pregnant woman (Farrow) with the shrink next door. The premise works much better as farce, as Allen would prove in “Everyone Says I Love You.”

Imagine if Allen had taken the plot of “A Midsummer Night’s Sex Comedy” and filmed it in the chamber-drama style of “Interiors.” Doesn’t sound like a great idea, does it?

One of Allen’s less successful attempts at mixing comedy and drama is this tale of a neurotic woman (Radha Mitchell) who invades the lives of a couple she’s befriended and proceeds to wreak havoc. The story is told in two parallel ways, one grim, one funny. The “Sliding Doors” plotting is meant to pose the question of whether life is essentially tragic or comic, but this is pretty thin gruel for such a big question. (Even so, poor Will Ferrell seems lost.) Besides, Allen’s made the point over and over, in better movies than this one, that we don’t have to choose.

Allen’s version of Fellini’s “La Dolce Vita” is a satirical portrait of a world gone mad from its obsession with fame. Journalist Kenneth Branagh (imitating Allen’s vocal mannerisms and hand gestures, but not his humanizing vulnerability) chases fame like a moth, basking in his proximity to a narcissistic, hotel-room-smashing actor (Leonardo DiCaprio) and a succession of flighty actresses and models. Allen doesn’t have much of a point to make (Fame is shallow? And so are people who pursue it? Of course. And…?) except to rain contempt upon nearly all his characters for succumbing to a fascination with stardom that, let’s face it, helps make Allen’s own work possible.

Allen’s one-act play “Death” is pretty effective on stage, but re-worked into a screenplay, its Kafkaesque depiction of mob paranoia is surprisingly inert. Allen’s black-and-white dramedy is a tribute to the German Expressionist style of the silent film era (an effective way to display psychological states like paranoia and claustrophobia in visual, cinematic terms), and yet very little in this listless film works. Includes a cameo by Madonna as a circus performer that’s not her finest hour.

Allen must have been feeling particularly bitter about his lack of commercial success in America throughout the ’90s, and about being more appreciated in Europe than at home. Later, he’d channel those feelings productively by spending most of the next decade shooting in Europe, thereby finding new inspiration and recharging his creative batteries. But, in this film, he turns his frustration towards the hands that feed him (both the studio financiers and the fans, both at home and abroad). He plays a once-acclaimed director who’s fallen on hard times and gets a shot at a commercially viable comeback film, only to have his anxiety develop into psychosomatic blindness. He directs the movie anyway, with the few who know trying to cover for him. That’s not a bad idea for a sketch, but as a movie, it drags out. Plus, there’s the unsavory spectacle of the 66-year-old Allen romantically entangled with not one but two women who are about 35 years his junior (Tea Leoni and Debra Messing). Really, enough is enough already.

Playing a bitter, cranky mentor, Allen followed up “Hollywood Ending” by passing the romantic reins off to a much younger actor, Jason Biggs. Here, Allen dispenses bad advice to Biggs, who’s besotted with a neurotic woman (Christina Ricci) who claims to love him but seems to be willing to sleep with any guy in New York except him. Misogynist? Yes (and unusually so for Allen), but the male characters don’t come off any better; there’s more than enough misanthropy to go around. (Allen gives himself all the funniest lines, but yeesh, do you really want to spend time with his character, or any of these people?) This is the sourest work of Allen’s career. Fortunately, his next masterpiece (“Match Point”) was just two movies away.