The Best & The Rest: Every Woody Allen Film Ranked

20. “Midnight in Paris” (2011)
Allen’s breezy ode to the City of Lights and to the 1920s Paris literary salon scene, is actually somewhat similar to “Cafe Society” in that they are both films that are nostalgic about nostalgia itself — in love with an idea of love that really only exists as an idea. Superficially quite simple, with an unexplained time-travel hook taking a struggling contemporary novelist (Owen Wilson) and plonking him down amidst his heroes Hemingway, Fitzgerald, Gertrude Stein et al, the film is a fond, teary-eyed look at the glamor of the past and the danger of falling for what might have been instead of what is. Peppered with glittering cameos and supporting roles (Marion Cotillard, Corey Stoll, Kathy Bates, Allison Pill, Tom Hiddleston, Rachel McAdams, Michael Sheen etc) to our minds with its 4 Oscar nods and its glowing, adoring reviews, it was somewhat overpraised. But even if the reception was more a function of relief that, after a string of disappointments, an off-the-boil Allen seemed to be at least partially back on form, that doesn’t necessarily detract from the pleasures of this solid charmer either.

19. “Vicky Cristina Barcelona” (2008)
It’s more more muskily sensual than is standard for Woody Allen, who usually displays a more intellectualized and ironic approach to sex, but “Vicky Cristina Barcelona” is still an enjoyable trifle, a kind of exoticized romp that’s not as deep as some fans like to make out, but doesn’t need to be. With this steamy 4-way love affair between some extremely attractive people, Allen’s migration to unfamiliar shores bears fruit, even if stakes remain relatively frivolous. Neurotic Vicky (Rebecca Hall) and free-spirited Cristina (Scarlett Johansson) cross paths with Juan Antonio (Javier Bardem) and his tempestuous ex-wife María Elena (a sexy and funny Penélope Cruz, who won an Oscar), and the culture-clashing comedy of manners that ensues is fizzy, awkward fun, until Maria Elena’s passionate nature takes a dark turn. It’s all a bit redolent of the myths about Latin lovers, but Cruz and Bardem have amazing chemistry (no wonder they hooked up afterwards) and the final scene suggests a sadness and a kind of wisdom that for once gives the characters depth as people rather than archetypes, however amusing those archetypes might be.

18. “Blue Jasmine” (2013)
When Allen’s on form there is no better (male) writer/director of complicated and “difficult” female roles, and when that talent meets an actress on form, the results have been spectacular (think of Judy Davis in “Husbands and Wives,” Dianne Wiest in “Hannah and her Sisters” or Diane Keaton in “Annie Hall“). But the only time in recent years the stars have aligned in a comparable manner is with Cate Blanchett‘s Oscar-winning turn in “Blue Jasmine.” Supported by the always-terrific Sally Hawkins, the suddenly resourceless and disgraced socialite Jasmine is a self-involved, neurotic nightmare and Blanchett is fearless about plumbing her absolute lowest depths. In fact, her performance is so stellar, it kind of blasts the rest of the film, which involves not the most engaging or insightful plot Allen has ever delivered, off the screen. “Blue Jasmine” could have been stronger in other departments, especially as its themes of affluence vanished overnight as a result of shady financial deals has more pointed topicality than we usually see from Allen. But as it is it’s almost wholly a vehicle for a towering Blanchett, and who can complain about that?

17. “Bananas” (1971)
Opening with one of his all-time best set pieces — the assassination of a foreign dictator being covered by a Howard Cosell and edited at a brisk, dare we say, experimental clip — if “Bananas” is ultimately not the most rewarding of Allen’s earlier, wackier films, it is still a lot of fun, combining moments of sublime silliness with more standard-issue observational New York living stuff. The foreign plot, which involves Allen becoming the leader of a fictional South American country in order to impress a girl, is less successful than the rest of the film, seemingly based on a mash-up of his short story writing and somewhat surrealist stand-up routines, that doesn’t quite work when translated to film. But the more familiar Allen-Manhattan-relationship stuff is an early goldmine, that includes a hilarious break-up sequence when Allen and his paramour discuss “giving” and “receiving” endlessly. “Bananas” never quite reaches the gonzo highs of “Love and Death,” and while it remains probably less dated than “Sleeper” is also lacks that film’s most inspired highs. But it’s does have what no other Allen film can boast: Sylvester Stallone in an early scene as a subway mugger.

16. “Zelig” (1983)
A curio in a filmography that is distinguished by repeating themes, “Zelig” dresses Allen’s typical gripes and philosophizing up in a pioneering mockumentary package. Presented as a black-and-white documentary on Leonard Zelig (Allen), the “human chameleon”, the film is a portrait of a misfit accepted by society when he discovers the power to literally metamorphose into the people around him. With the use of then still-innovative blue screen tech, Allen hobnobs with Calvin Coolidge and comes within shooting distance of Adolf Hitler. The efforts to make the film look like an authentically aged piece of history are impressive even if they’ve been supplanted by the likes of “Forrest Gump” since, while a romance between Zelig and Dr. Fletcher (Mia Farrow) is sweet if thinly plotted. It’s more likely you’ll enjoy the film for the historical cameos, for the cleverness of the juggling between fact and fiction and for modern-day legends, like Saul Bellow and Susan Sontag who despite not being renowned as laugh-riots, manage to keep admirably straight faces while commenting on the phenomenon as if it really happened.

15. “Take The Money And Run” (1969)
Somewhat obscured by Allen’s more polished films to come, this solo directorial debut could, pound for pound, be the funniest film he’s ever made, because all he wants to do here is make you laugh. Told in the format of a fake documentary, a creative decision well before its time, “Take The Money And Run” follows the story of Virgil Starkwell, a criminal who robs banks in lieu of a successful professional life in the, ahem, legal sector. As Virgil stacks up ignominies, we see the first stirrings of Allen’s romantic side, with a genuine relationship that develops amongst the madcap slapstick with Janet Margolin’s Louise. ‘Money’ manages to have this human center but still emphasizes the gags at the heart of the picture, in some ways establishing a template for heartfelt spoof that would later be credited erroneously to “Airplane!” Allen would go on to make pictures with more weighty ideas and concepts, but bits like the botched stickup attempt, the rainy prison escape with a gun made of soap and the utter slapstick genius of Virgil playing the cello in a marching band are some of the funniest moments ever committed to celluloid.

14.“Manhattan Murder Mystery” (1993)
It’s a strange world: in the throes of devastating personal scandal, Allen turned in his funniest, most optimistic and delightful film in years. In fact, two of the changes made as a result of outside pressures probably improved the film immeasurably: casting a spiky Anjelica Huston instead of a much younger actress to give Allen a slightly more age-appropriate flirtation, and more importantly, replacing Mia Farrow with a beguiling Diane Keaton — against whom a mock-irate Allen subsequently railed for getting more laughs than he does, despite the fact he’d written the material to make him look like the funny one. Actually, they’re both on top form, and the portrait of a long-term marriage that finds much-needed spice when a neighbor dies (finally turning to the murder sub-plot famously excised from “Annie Hall”), is one of the most endearing depictions of an adult relationship that Allen has ever managed. It’s peppered with allusions to classic films, fun until the end when it unashamedly rips one off, but that’s just nitpicking, especially in a movie that sends you giggling into the credits on a final gag worthy of Billy Wilder and I.A.L Diamond.

13. “The Purple Rose of Cairo” (1985)
Woody Allen made quite a few excellent movies with his ex-partner Mia Farrow in his middle period, as exemplified by this one about a battered wife (Farrow) during the Great Depression. When she goes to the movie theater to escape her troubles, Ted Baxter (Jeff Daniels), one of the characters in the film-within-the-film “The Purple Rose of Cairo,” breaks the fourth wall and comes off the screen to declare his love for her. Hijinks ensue in which Hollywood bigwigs try to separate the world of fiction from reality with increasingly intricate and difficult questions being raised by the wish-fulfillment scenario it posits. The film is one of Allen’s best (he’s said it’s the film that came closest to being exactly as he had envisaged it would) and it also explores our fascination with the moving image in a more serious-minded way than its light touch suggests. In fact, for most of its running time it’s a delightful coming-into-your-own comedy until a perfectly sad, borderline heartbreaking ending that shows up the movies for the beautiful lie they are.

12. “Stardust Memories” (1980)
“Stardust Memories” has been called a homage to Fellini‘s “8 1/2,” though as Tony Roberts says in the movie — “Homage? We outright stole it.” Allen breaks a number of social (and filmmaking) conventions before the film ends. He talks about the emptiness of success and celebrity (the ultimate American taboo) and the futility of romantic love. These are, of course, subjects Allen has touched on previously in his other films but never with such a feeling of despair, despite the quips. The dreamy feel owes a lot to cinematographer Gordon Willis, who can pivot the black-and-white footage from lush to surreal to stark from one shot to the next without losing fluidity. The flashbacks that we aren’t sure are flashbacks are equally dazzling, while the Godard-ian jump cuts add to the dizzying meta film-within-a-film narrative. The characters are more like two-dimensional memories brought to life, lacking depth but overflowing in significance. However the futility of searching for meaning within is also one of the last and best jokes in the film: ”What do you think was the significance of the Rolls-Royce?” someone asks. ”I think it represented his car,” is the answer.

11. “Broadway Danny Rose” (1984)
While Woody Allen is rightly regarded as a film legend, people often forget that he’s also one of the last remaining links to an earlier showbiz world, having started his career as a comedy writer for folks like Herb Shriner and Sid Caesar, in an era when showbiz promoters were often as colorful as the acts they represented. Enter “Broadway” Danny Rose, played by Allen himself, the legendarily inept yet good-hearted huckster with an unshakeable faith in his stable of z-list talents — “Never took a lesson in her life!” he exclaims in admiration of his wine-glass-playing act. The black-and-white film is told in flashback as a Greek chorus of comedians sit around at a table at the famed Carnegie Deli and swap stories about the agent, and his spot of bother with a mafioso and his moll played by an inspired Mia Farrow. But the plot is merely the hook to hang a series of increasingly funny, absurd and touching anecdotes on, a tribute to bygone days and personalities that also gave Allen himself one of his most lovable acting roles ever.