Woody Allen is a four-time Academy Award winner who has proved incredibly prolific in his decades-long career, writing, directing, and oftentimes starring in nearly a film a year for over 50 years. But how many of those are classics? Let’s take a look back at 25 of his greatest films, ranked worst to best.
After years as a joke writer and standup comic, Allen transitioned into filmmaking penning such screenplays as “What’s New Pussycat?” (1965) and starring in such titles as “Casino Royale” (1967). His first credit as a director was the comedically overdubbed Japanese spy thriller “What’s Up, Tiger Lily?” (1966).
The Woody Allen as we know him emerged in 1969 with the farcical mockumentary “Take the Money and Run” (1969), made when he was 34 years old. The success of that film led to a string of critically acclaimed absurdist comedies, including “Bananas” (1971) and “Sleeper” (1973).
He established himself as an important filmmaker with the romantic comedy “Annie Hall” (1977), which took home Oscars for Best Picture, Best Director, Best Original Screenplay (shared with Marshall Brickman), and Best Actress (Diane Keaton). A mature, hilarious look at a failed relationship, the film showcased Allen’s talent for telling insightful stories about the human condition, oftentimes set in New York City with some catchy jazz tunes.
Allen became a frequent presence at the Academy Awards, winning twice more for Best Original Screenplay (“Hannah and Her Sisters” and “Midnight in Paris”). He has contended an astonishing 20 additional times: once for acting (“Annie Hall”), six for directing (“Interiors,” “Broadway Danny Rose,” “Hannah and Her Sisters,” “Crimes and Misdemeanors,” “Bullets Over Broadway,” and “Midnight in Paris”), and 13 for screenwriting (“Interiors,” “Manhattan,” “Broadway Danny Rose,” “The Purple Rose of Cairo,” “Radio Days,” “Crimes and Misdemeanors,” “Alice” “Husbands and Wives,” “Bullets Over Broadway,” “Mighty Aphrodite,” “Deconstructing Harry,” “Match Point,” and “Blue Jasmine”).
Tour our photo gallery above of Allen’s 25 greatest films, including a few for which he somehow didn’t receive Oscar nominations. Can you guess which is in our #1 slot and which movies are in the top five?
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25. ALICE (1990)
Image Credit: Orion/Kobal/REX/Shutterstock Written by Woody Allen. Starring Alec Baldwin, Blythe Danner, Judy Davis, Mia Farrow, William Hurt, Keye Luke, Joe Mantengna, Bernadette Peters.
Allen’s love of mysticism is evident throughout “Alice,” a modestly entertaining reimagining of Federico Fellini’s “Juliet of the Spirits.” Mia Farrow plays the titular character, a wealthy Manhattan housewife who starts to reevaluate her life after visiting a Chinese herbalist (Keye Luke). His potions help her take a deeper look at her relationships, including with her patronizing husband (William Hurt), her dead lover (Alec Baldwin), and the jazz musician (Joe Mantenga) who catches her eye. The film brought Allen yet another Oscar nomination for Best Original Screenplay, plus a Golden Globe bid for Farrow in their Musical/Comedy category.
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24. TAKE THE MONEY AND RUN (1969)
Image Credit: Abc/Rollins-Joffe/Cinerama/Kobal/REX/Shutterstock Written by Woody Allen and Mickey Rose. Starring Woody Allen, Janet Margolin, Louise Lasser.
Though his official directorial debut was the comedically overdubbed Japanese spy thriller “What’s Up, Tiger Lily?,” the Woody Allen as we know him emerged triumphantly with this hilarious mockumentary farce. He stars as Virgil Starkwell, an inept bank robber who turns to crime after a failed music career. The script by Allen and Mickey Rose plays more like a collection of humorous bits than a fully-formed story. Luckily, many of those bits are uproariously funny. Interestingly enough, Allen decided to helm this script on his own after unhappy experiences on “Casino Royal” and “What’s New, Pussycat?”
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23. MANHATTAN MURDER MYSTERY (1993)
Image Credit: Tri-Star/Rollins-Joffe/Kobal/REX/Shutterstock Written by Woody Allen and Marshall Brickman. Starring Alan Alda, Woody Allen, Anjelica Huston, Diane Keaton.
“Manhattan Murder Mystery” is the Wood-man at his most playful, a sly and charming whodunit about a middle-aged couple (Allen and Diane Keaton) investigating the puzzling death of their neighbor’s wife. Alan Alda and Anjelica Huston give hilarious support as the duo’s friends. It’s utterly delightful to see Allen and Keaton together again after so many years apart, in what was originally intended to be a subplot for their Oscar-winning “Annie Hall.” Although Keaton contended at the Golden Globes and Huston was nominated at the BAFTAs, the Academy didn’t have much of a funny bone when it came to this one.
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22. MIGHTY APHRODITE (1995)
Image Credit: Snap/REX/Shutterstock Written by Woody Allen. Starring F. Murray Abraham, Woody Allen, Claire Bloom, Helena Bonham Carter, Olympia Dukakis, Michael Rapaport, Mira Sorvino, David Ogden Stires, Jack Warden, Peter Weller.
Allen doesn’t often dip his toes into the ribald, which makes “Mighty Aphrodite” all the more refreshingly funny. He plays a New York sportswriter who becomes obsessed with finding the birthmother of his adopted son as his marriage is falling apart. Much to his surprise, his search leads him to a porn star and hooker (Mira Sorvino). Sorvino won Best Supporting Actress at the Oscars, and it’s easy to see why: at times ditzy, vulgar, and cheerful, she creates a surprisingly sympathetic character who holds her own comedically against Allen. The film brought him another Oscar nomination for screenwriting.
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21. SWEET AND LOWDOWN (1999)
Image Credit: Magnolia/Sweetland/Doumanian Prods/Kobal/REX/Shutterstock Written by Woody Allen. Starring Anthony LaPaglia, Brian Markinson, Gretchen Mol, Samantha Morton, Sean Penn, Uma Thurman, James Urbaniak, John Waters.
Jazz has functioned almost like an off-screen character in Allen’s oeuvre, so it’s not surprising he would eventually make a film about a musician. Sean Penn plays Emmet Ray, an immensely confident 1930s jazz guitarist who lives forever in the shadows of Django Reinhardt. The heart of the story lies in his romance with a cheerful deaf girl (Samantha Morton), who sticks by his side despite his run-ins with the mob and an affair with a floozy (Uma Thurman). Though Penn and Morton were nominated at the Oscars in Best Actor and Best Supporting Actress, respectively, Allen was ignored for writing and directing this charming bauble.
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20. DECONSTRUCTING HARRY (1997)
Image Credit: Fine Line Features/Kobal/REX/Shutterstock Written by Woody Allen. Starring Caroline Aaron, Woody Allen, Kirstie Alley, Bob Balaban, Richard Benjamin, Eric Bogosian, Billy Crystal, Hazelle Goodman, Mariel Hemingway, Amy Irving, Julie Kavner, Eric Lloyd, Julia Louis-Dreyfus, Tobey Maguire, Demi Moore, Elisabeth Shue, Stanley Tucci, Robin Williams.
It’s rather shocking to see “Deconstructing Harry,” a raunchy comedy about an alcoholic, sex-crazed novelist (Allen) wallowing in the ashes of the bridges he’s burned. To hear crude, profanity-laced dialogue pour out of the star’s mouth will make you do a double-take, especially when you consider he’s probably saying what’s really on his mind. Yet by laying himself so bare at a time when he was embroiled in scandal, he created one of his most bracing works ever. A reimagining of “Wild Strawberries,” this is a profane, probing, and painful look at the creative process. The film brought Allen another Oscar nomination for screenwriting.
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19. ZELIG (1983)
Image Credit: Brian Hamill/Orion/Warner Bros/Kobal/REX/Shutterstock Written by Woody Allen. Starring Woody Allen, Mia Farrow.
Allen kicked off his directing career with the mockumentary “Take the Money and Run,” and with “Zelig,” he creates an even more technically dazzling sendup of nonfiction filmmaking. Set in the 1920s, it tells the “true” story of Leonard Zelig (Allen), a human chameleon who, in a desperate attempt to fit in, is able to match the appearance of whoever he’s around, making him a sensation. Frequent collaborator Gordon Willis reaped an Oscar nomination for his cinematography, which meticulously recreates the grit and grime of early newsreel footage while seamlessly placing Allen amongst early 20th century celebs.
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18. ANOTHER WOMAN (1988)
Image Credit: Orion/Kobal/REX/Shutterstock Written by Woody Allen. Starring Philip Bosco, Betty Buckley, Blythe Danner, Sandy Dennis, Mia Farrow, Gene Hackman, Ian Holm, John Houseman, Martha Plimpton, Gena Rowlands, David Ogden Stiers, Harris Yulin.
Allen’s admiration for Ingmar Bergman is no secret, and “Another Woman” is one of his most accomplished tributes to the Swedish auteur. Gena Rowlands stars as a college professor facing a midlife crisis. She rents an apartment hoping to finish a new book, only to find out it’s next door to a psychiatrist’s office. As she overhears the musings of a depressed pregnant woman (Mia Farrow), she starts to re-evaluate her own life. Allen uses flashbacks, dream sequences, and narration to paint a portrait of regret. Gene Hackman and Ian Holm appear as the love Rowlands lost and the unfaithful man she married, respectively.
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17. VICKY CRISTINA BARCELONA (2008)
Image Credit: Weinstein Co./Mediapro/Gravier Prods./REX/Shutterstock Written by Woody Allen. Starring Javier Bardem, Penelope Cruz, Scarlett Johansson, Patricia Clarkson, Kevin Dunn, Rebecca Hall, Chris Messina.
Recent years have found Allen leaving New York City to travel around Europe, and his creativity has flourished because of it. With “Vicky Cristina Barcelona,” he journeys to Spain for a sensual and satiric story about two college students (Scarlett Johansson and Rebecca Hall) who fall under the spell of a charismatic painter (Javier Bardem) while traveling abroad during the summer. Penelope Cruz won the Oscar as Best Supporting Actress for playing Bardem’s fiery, unstable ex-wife, who brings complications to his new affair. Despite winning the Golden Globe for Best Comedy/Musical Film and reaping a WGA bid, Allen was snubbed at the Oscars.
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16. MATCH POINT (2005)
Image Credit: Clive Coote/Jada Prods/BBC F/REX/Shutterstock Written by Woody Allen. Starring Brian Cox, Matthew Goode, Scarlett Johansson, Emily Mortimer, Jonathan Rhys-Meyers, Penelope Wilton.
After years of toothless comedies, many of them pale reflections of his earlier masterpieces, Allen came roaring back with this sexy, noirish thriller. There’s nary a giggle to be found in “Match Point,” which stars Jonathan Rhys-Myers as a poor Irish tennis player who marries into a wealthy English family. But he soon finds himself drawn to an alluring American (Scarlett Johansson), and their affair sets off a tragic chain of events. Moving the action across the pond from his native New York proved a welcome breath of fresh air for the filmmaker, who was honored with yet another Oscar nomination for Best Original Screenplay.
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15. BROADWAY DANNY ROSE (1984)
Image Credit: Orion/Rollins-Joffe/Kobal/REX/Shutterstock Written by Woody Allen. Starring Woody Allen, Mia Farrow, Nick Apollo Forte, Milton Berle.
Allen got his start as a joke writer for Sid Caesar, and “Broadway Danny Rose” is a loving tribute to the old school vaudevillians of that era. He plays the titular character, a hapless talent agent representing oddball talents, from a blind xylophonist to piano-playing birds. In his attempts to reconcile a washed-up crooner (Nick Apollo Forte) with his tough-as-nails mistress (Mia Farrow), he gets mistaken as her boyfriend by a jealous gangster. Rather than ridicule his pathetic performers, Allen creates a great deal of poignancy for these lovable losers. He scored writing and directing bids at the Oscars, winning the WGA and BAFTA prizes for his script.
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14. BANANAS (1971)
Image Credit: Rollins-Joffe/United Artists/Kobal/REX/Shutterstock Written by Woody Allen and Mickey Rose. Starring Woody Allen, Louise Lasser, Carlos Montalban, Natividad Abascal.
With “Bananas,” the title tells you pretty much everything you need to know. Like many of Allen’s early films, this is an uneven hodgepodge of good jokes, terrible jokes, and diversions into the bizarre and fanciful. It’s also very, very funny. Allen stars as a floundering New Yorker who falls in love with a political activist (Louise Lasser). When she leaves him, he flies down to an impoverished Central American nation and gets swept up in their latest rebellion, inexplicably becoming El Presidente. It’s not so much the destination you watch this one for as the zany roads that gets you there, and Allen is an hilariously nebbish guide.
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13. STARDUST MEMORIES (1980)
Image Credit: United Artists/Rollins-Joffe/Kobal/REX/Shutterstock Written by Woody Allen. Starring Woody Allen, Charlotte Rampling, Jessica Harper, Marie-Christine Barrault, Tony Roberts.
Allen paid tribute to Federico Fellini with his own version of “8 1/2,” much to the confusion of critics and consternation of fans. “Stardust Memories” centers on Sandy Bates (Allen), a prominent movie director facing a crippling creative block. While attending a weekend retrospective of his work, he reflects on fame, his work, and his failed relationships while dealing with a host of grotesqueries. Autobiographical in the extreme, the film was panned by audiences who felt the director was thumbing his nose at them for liking his work. Yet seen today, this black-and-white fever dream is an effective examination of art and inspiration.
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12. INTERIORS (1978)
Image Credit: United Artists/Rollins-Joffe/Kobal/REX/Shutterstock Written by Woody Allen. Starring Geraldine Page, Diane Keaton, Mary Beth Hurt, Kristin Griffith, Richard Jordan, E. G. Marshall, Maureen Stapleton, Sam Waterson.
After making a name for himself as a master of ridiculous comedy, Allen turned deathly serious for this followup to his Oscar-winning “Annie Hall.” A dour, unsettling drama with echoes of Ingmar Bergman and Eugene O’Neill, “Interiors” centers on three sisters (Diane Keaton, Mary Beth Hurt, Kristin Griffith) who find their lives spiraling out of control when their father (E. G. Marshall) leaves their emotionally unstable mother (Geraldine Page). Their lives are further complicated when their dad brings home another woman (Maureen Stapleton). The Academy reward Allen’s first foray into drama with writing and directing nominations.
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11. HUSBANDS AND WIVES (1992)
Image Credit: Tri-Star/Kobal/REX/Shutterstock Written by Woody Allen. Starring Woody Allen, Blythe Danner, Judy Davis, Mia Farrow, Juliette Lewis, Liam Neeson, Sydney Pollack.
It’s hard to watch “Husbands and Wives” without thinking of the context with which it was made. This comedic drama about the breakup of two couples came out months after Allen and Mia Farrow split over the director’s affair with Farrow’s adopted daughter, Soon-Yi Previn, giving certain scenes an almost eerie reality. Yet even outside of those circumstances, this is still a bracing and hilarious examination of marital strife, shot in a quasi-documentary style and filled with terrific performances, including Supporting Actress nominee Judy Davis as a spurned divorcee. The film brought Allen another Oscar bid for Best Original Screenplay.
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10. SLEEPER (1973)
Image Credit: United Artists/Rollins-Joffe/Kobal/REX/Shutterstock Written by Woody Allen and Marshall Brickman. Starring Woody Allen, Diane Keaton, John Beck, Marya Small, Susan Miller.
The best of Allen’s early comedies is this futuristic farce about a health food store owner (Allen) who enters the hospital for a routine operation and wakes up 200 years later after being cryogenically frozen. He’s thawed out by a group of radical scientists who want his help overthrowing an unseen leader who rules with an iron fist. Diane Keaton costars as a socialite who believes the world is great as is, until she goes on the run with Allen, that is. Originally conceived as a silent movie, the director supplies us with one hilarious sight gag after another, most notably a sequence in which he poses as a robot for wealthy stoners.
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9. RADIO DAYS (1987)
Image Credit: Orion/Rollins-Joffe/Kobal/REX/Shutterstock Written by Woody Allen. Starring Danny Aiello, Jeff Daniels, Mia Farrow, Seth Green, Robert Joy, Julie Kavner, Diane Keaton, Julie Kurnitz, Renee Lippin, Kenneth Mars, Josh Mostel, Tony Roberts, Wallace Shawn, Michael Tucker, David Warrilow, Diane Wiest.
Allen takes a nostalgic look back at his own childhood with this loving tribute to the days before television took all the imagination out of entertainment. Set in the late 1930s and early 1940s, the film centers on a Jewish-American family in Rockaway Beach who spend their days glued to the radio. Allen, who also narrates, fills the film with personal observations so specific they become universal. He also contrasts the lives of working class listeners with those of the glamorous Manhattan stars they idolize, casting the likes of Diane Keaton, Jeff Daniels, and Wallace Shawn in cameos. The film brought him yet another Oscar bid for writing.
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8. BLUE JASMINE (2013)
Image Credit: Moviestore/REX/Shutterstock Written by Woody Allen. Starring Alec Baldwin, Cate Blanchett, Louis C.K., Bobby Cannavale, Andrew Dice Clay, Sally Hawkins, Peter Sarsgaard, Michael Stuhlbarg.
A sort of “Streetcar Named Desire” for the digital age, “Blue Jasmine” centers on a New York socialite (Cate Blanchett) whose life spirals out of control when she moves to San Francisco to stay with her sister (Sally Hawkins) after her husband (Alec Baldwin) kills himself. Blanchett won a well-deserved Best Actress Oscar for playing Jasmine, a woman so steeped in denial and delusion she barely notices the havoc she’s wreaking. Supporting Actress nominee Hawkins nearly matches her as Ginger, a sweat-natured nymph facing her own marital woes. Allen was once again nominated at the Oscars for his original screenplay.
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7. MIDNIGHT IN PARIS (2011)
Image Credit: Gravier Productions/Kobal/REX/Shutterstock Written by Woody Allen. Starring Kathy Bates, Adrien Brody, Carla Bruni, Marion Cotillard, Rachel McAdams, Michael Sheen, Owen Wilson, Alison Pill, Tom Hiddleston, Corey Stoll, Lea Seydoux.
Allen won his fourth Oscar for penning this romantic ode to the city of lights. Owen Wilson stars as a nostalgic screenwriter vacationing in Paris with his fiancee (Rachel McAdams). He suddenly finds himself transported back to the 1920s, where he rubs elbows with the likes of Ernest Hemingway (Corey Stoll), Gertrude Stein (Kathy Bates), and Salvador Dali (Adrien Brody). Yet the Golden Age isn’t exactly that for the people living through it. “Midnight in Paris” was a massive hit, grossing more than any of Allen’s previous works. In addition to his screenplay victory, he also contended for directing, and the film competed for Best Picture.
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6. BULLETS OVER BROADWAY (1994)
Image Credit: Brian Hamill/Magnolia/Sweetland/Kobal/REX/Shutterstock Written by Woody Allen and Douglas McGrath. Starring Jim Broadbent, John Cusack, Harvey Fierstein, Chazz Palminteri, Mary-Louise Parker, Rob Reiner, Jennifer Tilly, Tracey Ullman, Joe Viterelli, Jack Warden, Dianne Wiest.
An unlikely mixture of theatrical satire and gangland epic, “Bullets Over Broadway” is one of Allen’s most delightful concoctions yet. It centers on a struggling 1920s playwright (John Cusack) who will do anything to get his latest important drama to the stage, even casting a screechy-voiced mob moll (Jennifer Tilly) so her boyfriend (Joe Viterelli) will put up the money. She comes complete with a guard (Chazz Palminteri) who knows a great deal about dramatic structure. Dianne Wiest won her second Supporting Actress Oscar (both of them for Allen films) as a drunken grande dame of the theater. Allen also competed for writing and directing.
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5. THE PURPLE ROSE OF CAIRO (1985)
Image Credit: Orion/Rollins-Joffe/Kobal/REX/Shutterstock Written by Woody Allen. Starring Mia Farrow, Danny Aiello, Edward Herrmann, John Wood, Deborah Rush, Zoe Caldwell, Van Johnson, Karen Akers, Milo O’Shea, Dianne Wiest.
This bittersweet romantic fantasy centers on a Depression-era waitress (Mia Farrow) who escapes her abusive husband (Danny Aiello) by going to the movies. She becomes enamored with an entertaining bauble about a happy-go-lucky archeologist (Jeff Daniels), and one day he walks off the screen and into her life, prompting the film’s star (Daniels) to leave Hollywood and track down his creation. At times sentimental and charming, the film is ultimately a devastating examination of the dashed dreams that keep our realities going. Allen was once again nominated at the Oscars for screenwriting, winning at the Golden Globes and BAFTA.
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4. CRIMES AND MISDEMEANORS (1989)
Image Credit: Brian Hamill/Orion/Rollins-Joffe/Kobal/REX/Shutterstock Written by Woody Allen. Starring Caroline Aaron, Alan Alda, Woody Allen, Claire Bloom, Mia Farrow, Joanna Gleason, Anjelica Huston, Martin Landau, Jenny Nichols, Jerry Orbach, Sam Waterson.
With “Crimes and Misdemeanors,” Allen showcases his talents for comedy and drama with parallel stories of morality. Martin Landau stars as a prominent ophthalmologist who decides to have his volatile mistress (Anjelica Huston) murdered before she can reveal their affair to his wife. Meanwhile, a struggling documentarian (Allen) sacrifices artistic integrity to make a movie about his arrogant brother-in-law (Alan Alda), a successful TV producer. At the same time, he finds himself falling in love with his producer (Mia Farrow). Allen earned writing and directing Oscar bids for the film, which raises several tough questions and offers few easy answers.
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3. MANHATTAN (1979)
Image Credit: Brian Hamill/United Artists/Rollins-Joffe/Kobal/REX/Shutterstock Written by Woody Allen and Marshall Brickman. Starring Woody Allen, Diane Keaton, Michael Murphy, Mariel Hemingway, Meryl Streep, Anne Byrne.
Allen’s love for New York City has never been more lovingly on display than in this pitch-perfect romantic comedy, shot in widescreen black-and-white by Gordon Willis and set to the beat of some classic Gershwin tunes. He stars as Isaac, a 42-year-old divorced sportswriter dating a teenager (Mariel Hemingway) who suddenly finds himself enamored with his best friend’s (Michael Murphy) mistress (Diane Keaton). The city of Manhattan is almost a character itself, with everything from Central Park to the Guggenheim providing a backdrop for the drama. Allen and Marshall Brickman competed at the Oscars for Best Original Screenplay.
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2. HANNAH AND HER SISTERS (1986)
Image Credit: Brian Hamill/Orion/Rollins-Joffe/Kobal/REX/Shutterstock Written by Woody Allen. Starring Woody Allen, Michael Caine, Mia Farrow, Carrie Fisher, Barbara Hershey, Lloyd Nolan, Maureen O’Sullivan, Daniel Stern, Max von Sydow, Dianne Wiest.
Neatly divided into chapter breaks, “Hannah and Her Sisters” looks at the uncontrollable messiness of life. Allen’s Oscar-winning script about three sisters (Mia Farrow, Barbara Hershey, Dianne Wiest) and their family is pretty close to perfection in creating sharp, three-dimensional characters struggling with their own destinies. Michael Caine won Supporting Actor for playing a man desperately in love with his wife’s (Farrow) sister (Hershey), while Wiest won Supporting Actress as the perennial black sheep. Allen, who also appears as a man afraid of dying, contended for directing this crowdpleaser, which was also nominated for Best Picture.
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1. ANNIE HALL (1977)
Image Credit: Moviestore/REX/Shutterstock Written by Woody Allen and Marshall Brickman. Starring Woody Allen, Diane Keaton, Tony Roberts, Carol Kane, Paul Simon, Janet Margolin, Shelley Duvall, Christopher Walken, Colleen Dewhurst.
With “Annie Hall,” Allen moved into more mature filmmaking after establishing himself as the premiere joke-maker. At the same time, this small-scale story about a New York comedian (Allen) and an eccentric lounge singer (Diane Keaton) broke the mold for romantic comedies, bringing a darker and more realistic edge to the genre. That’s not to say it’s without its flights of fancy, some of them the best gags of Allen’s career. Yet it’s Keaton’s Oscar-winning performance as the sweet, quirky Annie that makes this one sing. Allen took home prizes for writing and directing, and the film became one of the few laugh-fests to win Best Picture.
