The best Woody Allen movies all mostly deal with quirky people in uncomfortable situations, often musing about life and its idiosyncrasies. Allen is one of the most acclaimed American filmmakers in history, with a record 16 nominations for the Oscar for Best Original Screenplay, while winning four Academy Awards during his career. He has also been recognized by the BAFTA Awards, Golden Globe Awards, Tony Awards, Emmy Awards, and even the Grammys. He also won the Golden Globe Cecil B. DeMille Award in 2014.
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Allen started his career as a writer for television before moving on to films, where he developed a reputation for dialogue-driven dramas, often with long monologs, sometimes performed by Allen himself. He has made everything from slapstick comedies to romantic comedies to dramas and psychological thrillers, and for several years, he seemed to have his choice of the best actors in Hollywood, clamoring to work with him. In 2023, Allen released his 50th directed movie with Coup de chance.
10 Match Point (2005)
A Psychological Thriller In The World Of Tennis
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Match Point RCrimeDocumentaryDramaRomanceThriller Where to Watch
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*Availability in US Director Woody Allen Release Date October 26, 2005 Cast Jonathan Rhys Meyers , Alexander Armstrong , Paul Kaye , Matthew Goode , Brian Cox , Penelope Wilton Runtime 124 minutes
In 2005, Woody Allen worked with Scarlett Johansson on the psychological thriller Match Point. Jonathan Rhys Meyers stars as a former professional tennis player named Chris Wilton who marries into a wealthy family but finds his life turned upside down when he enters into an affair with his brother-in-law’s girlfriend Nola (Johansson). When Nola pressures Chris to divorce his wife and come to her, he finds that his entire social status could be upended if he does it, so he makes the worst possible decision.
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Woody Allen considers it one of his best movies.
This is a much darker film than many of Allen’s releases, and it shares much in common with film noirs and modern-day psychological thrillers. The film received positive reviews, sitting at 77% fresh on Rotten Tomatoes, and Woody Allen considers it one of his best movies (via The Age). The Oscars awarded Allen a Best Original Screenplay nomination, and it was also nominated for four Golden Globe Awards, two for Allen, one for Best Motion Picture – Drama, and one for Johansson. It didn’t win any of the awards though.
9 The Purple Rose Of Cairo (1985)
A Fantasy Romantic Comedy About A Film Character Who Enters The Real World
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The Purple Rose of Cairo FantasyComedyRomance
The Purple Rose of Cairo is a film set during the Great Depression, following Cecilia, a New Jersey waitress who finds solace in the cinema. Repeatedly watching a film featuring archaeologist Tom Baxter, she uses the fantasy world as an escape from her dreary existence after losing her job.
Release Date March 1, 1985 Cast Jeff Daniels , Mia Farrow , Danny Aiello , Irving Metzman , Stephanie Farrow , Edward Herrmann , John Wood , Deborah Rush , Van Johnson , Zoe Caldwell , Milo O’Shea , Dianne Wiest , Glenne Headly , Paul Herman , Rick Petrucelli , Peter Castellotti , John Rothman , David Kieserman , Elaine Grollman , Victoria Zussin , Mark Hammond , Wade Barnes , Joseph G. Graham , Don Quigley , Maurice Brenner Runtime 82 minutes Expand
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In 1985, Woody Allen directed the fantasy romantic comedy The Purple Rose of Cairo, which sees a movie character come into the real world to pursue a woman watching him in his film. Mia Farrow stars as Cecilia, a woman in an abusive marriage who loses her job. She distracts herself by going to the movies and focusing on a character in the film named Tom Baxter. When Tom notices he is being watched, he steps out of the picture and begins to date Cecelia, which causes the characters in the movie to stop performing.
Reviews praised Allen’s direction and script as “lighthearted and sweet” and called it one of his more “whimsical” pictures.
The actor who plays Tom (Jeff Daniels) shows up in town to fix the problem, and he sets out to ruin their relationship to force Baxter back into the movie. Critics loved the release, giving it a 93% fresh rating on Rotten Tomatoes. Reviews praised Allen’s direction and script as “lighthearted and sweet” and called it one of his more “whimsical” pictures. Allen earned an Oscar nomination for Best Original Screenplay and won a BAFTA for that, as well as for Best Film.
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8 Blue Jasmine (2013)
A Manhattan Socialite Has To Move In With Her Working-Class Sister
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blue jasmine pg-13Drama
Blue Jasmine is a 2013 Woody Allen-directed film starring Kate Blanchett. The comedy-drama revolves around Jasmine, a wealthy Manhattan socialite who is forced to move into her sister’s apartment in San Francisco. The film stars Sally Hawkins as Jasmine’s sister, along with Alex Baldwin and Peter Sarsgaard. Blue Jasmine also won the Oscar for Best Performance by an Actress in a Leading Role at the 2014 Academy Awards.
Director Woody Allen Release Date August 23, 2013 Distributor(s) Sony Cast Cate Blanchett , Sally Hawkins Runtime 98minutes
Released in 2013, Woody Allen directed the comedy-drama Blue Jasmine, which saw Cate Blanchett star as Jasmine Francis, a Manhattan socialite who has fallen on hard times. She had a nervous breakdown and went into heavy debt, forced to move in with her sister Ginger (Sally Hawkins), a working-class woman in San Francisco. Jasmine’s husband was arrested for fraud, and one of his targets was Ginger and her husband. After Jasmine’s husband, Hal, dies by suicide, her life falls apart.
Related The 8 Movies That Defined Cate Blanchett’s Career
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Critics praised the film, awarding it a 90% fresh rating on Rotten Tomatoes, which said it was Allen at his “peak late-period form.” Reviews also praised Cate Blanchett’s performance as a woman falling apart and so deep in her own delusions that she seemed to have no way out. The film received three Oscar nominations, with Blanchett winning for Best Actress, while Sally Hawkins was nominated for Best Supporting Actress and Allen for Best Original Screenplay.
7 Bullets Over Broadway (1994)
A Black Comedy Crime Film About A Playwright Forced To Cast A Mobster’s Girlfriend
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Bullets Over Broadway RComedyCrime
Bullets Over Broadway (1994) is a comedic drama that delves into the world of 1920s theater, where a struggling playwright is forced to cast a mobster’s talentless girlfriend in his latest production. The film explores themes of artistic integrity, compromise, and the clash between creative ambitions and external pressures. Directed by Woody Allen, it features strong performances from an ensemble cast, balancing humor with a satirical look at show business.
Director Woody Allen Release Date October 14, 1994 Cast John Cusack , Chazz Palminteri , Dianne Wiest , Jennifer Tilly , Mary-Louise Parker , Tracey Ullman , Jim Broadbent , Joe Viterelli , Harvey Fierstein , Rob Reiner , Jack Warden , Tony Sirico , Victor Colicchio , Louis Eppolito , Gene Canfield , Peter Castellotti , Tony Conforti Runtime 98 Minutes Expand
In Bullets Over Broadway, a struggling playwright needs to find a way to get his new production financed and agrees to cast the untalented girlfriend of a notorious mobster to get the money. John Cusack stars as David Shayne, an idealistic playwright who arrives on Broadway from Pittsburgh and seeks financing from a gangster named Nick Valenti (Joe Viterelli). However, the only way to get the money is to cast Nick’s girlfriend, Olive (Jennifer Tilly), in the play.
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Soon, a henchman named Cheech (Chazz Palminteri) starts accompanying Olive to the rehearsals and gives his own notes to David, which are surprisingly good ideas. However, with success comes turmoil for everyone involved. Critics gave the movie a very high 95% Rotten Tomatoes rating, and the Oscars awarded it seven nominations, including Best Director and three different acting nominations. Dianne Wiest won for Best Supporting Actress.
6 Crimes And Misdemeanors (1989)
A Mistress Threatens To Reveal An Affair Which Leads To Murderous Results
Crimes and Misdemeanors is an existential comedy-drama that follows a reputable ophthalmologist named Judah (Alan Alda), who is cheating on his wife, and a documentary filmmaker named Clifford (Woody Allen). Judah sets up the murder of his mistress to protect his own reputation, while Cliff finds his love for a woman rebuffed when she chooses to be with someone that Cliff despises. Their two stories parallel each other and then end with the two men crossing paths.
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Critics praised the film with a 92% positive score on Rotten Tomatoes, most of the praise going to the script by Allen.
The movie’s theme is looking at moral dilemmas and whether people can continue in life knowing they did something terrible. The title and themes are all based on the Russian novel Crime and Punishment, although the movie’s ending is the opposite of the resolution from the novel. Critics praised the film with a 92% positive score on Rotten Tomatoes, most of the praise going to the script by Allen. Crimes and Misdemeanors picked up three Oscar nominations but didn’t win any.
5 Midnight In Paris (2011)
A Fantasy Time Traveling Movie In Paris
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6/10 Midnight in Paris pg-13RomanceFantasy
Written and directed by Woody Allen, Midnight in Paris stars Owen Wilson as Gil Pender, a struggling writer who, on a trip to Paris with his fiance, begins traveling back in time to the 1920s every night at midnight, leading him to meet and mingle with some of the city’s biggest names of the time. Besides Wilson, the cast includes Rachel McAdams, Tom Hiddleston, Kathy Bates, Marion Cotillard, Corey Stoll, and Adrien Brody.
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*Availability in US Director Woody Allen Release Date May 11, 2011 Distributor(s) Sony Cast Owen Wilson , Tom Hiddleston , Rachel McAdams , Marion Cotillard , Lea Seydoux Runtime 94minutes
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Woody Allen combined his love for classic cinema with a fantasy comedy story about a disillusioned screenwriter who finds himself traveling back in time to the Lost Generation of the 1920s in Paris. Owen Wilson is Gil Pender, a screenwriter who is vacationing in Paris with his fiancée Inez (Rachel McAdams), who is visiting her wealthy parents. However, he ends up traveling back in time to the 1920s and visiting with Zelda Fitzgerald, Ernest Hemingway, Gertrude Stein, Pablo Picasso, and more.
Related Rachel McAdams’ Accidental Time Travel Movie Series Explained
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Critics praised Midnight in Paris, awarding it a 93% fresh rating on Rotten Tomatoes, calling Allen’s script “sweetly sentimental” and “charming.” Owen Wilson also received praise for playing a role that Allen would have written for himself three decades earlier. Allen won the Oscar for Best Original Screenplay for Midnight in Paris while the movie also picked up nominations for Best Picture, Best Director, and Best Art Direction.
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4 Hannah And Her Sisters (1986)
A Comedy-Drama About An Extended Family
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Hannah and Her Sisters R Where to Watch
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*Availability in US Director Woody Allen Release Date February 7, 1986 Cast Mia Farrow , Michael Caine , Woody Allen , Carrie Fisher , Barbara Hershey , Dianne Wiest , Max Von Sydow Main Genre Drama
In 1986, Woody Allen directed Hannah and Her Sisters. The film is a family comedy-drama that takes place over two years, beginning and ending at the family’s Thanksgiving dinner. Mia Farrow stars as Hannah, Michael Caine as her husband, and Barbara Hershey and Dianne Wiest as her sisters. The main arc is about Hannah and her husband, Elliot, and their marriage problems when he has an affair with one of her sisters. Meanwhile, the other sister, Holly, is struggling with an acting career.
Allen structures the film similar to Ingmar Bergman’s Fanny and Alexander, focusing on three consecutive holidays, one in a time of contentment, the second in turmoil, and the third showing the outcome. Praise went to how Allen was able to switch between stories and keep things moving and interesting, awarding it a 91% fresh rating. Hannah and Her Sisters picked up seven Oscar nominations, winning Best Original Screenplay, Best Supporting Actor (Caine), and Best Supporting Actress (Dianne Wiest).
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3 Vicky Cristina Barcelona (2008)
Two American Women Vacation In Barcelona & Fall For The Same Man
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Vicky Cristina Barcelona RDramaDocumentaryRomance
Vicky Cristina Barcelona, directed by Woody Allen, follows friends Vicky and Cristina as they spend a summer in Barcelona. The film explores their differing philosophies on love and relationships as they encounter a charismatic artist and his tempestuous ex-wife. Starring Scarlett Johansson, Rebecca Hall, Javier Bardem, and Penélope Cruz, the film delves into the complexities of passion and self-discovery.
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*Availability in US Director Woody Allen Release Date August 15, 2008 Cast Rebecca Hall , Scarlett Johansson , Christopher Evan Welch , Chris Messina , Patricia Clarkson , Kevin Dunn Runtime 96 minutes
Scarlett Johansson and Rebecca Hall star as non-conformist Cristina and traditional Vicky go on vacation together in Barcelona . When there, they both meet an artist named Juan Antonio Gonzalo (Javier Bardem). Both women fall for him, but Cristina finally hooks up with him, only to learn he is still in love with his ex-wife Maria (Penélope Cruz), who suggests they enter a polygamist romantic relationship. However, things are never stable for any of the people involved.
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Things get even more complicated when Vicky becomes involved with Juan as well, making for an intriguing love rectangle. Critics praised the movie, awarding it an 80% fresh Rotten Tomatoes score, calling it a “beguiling tragicomedy” with praise going to the cast and the location shooting in Spain. Penélope Cruz won the film’s only Oscar nomination for Best Supporting Actress, while it also won Best Film – Musical or Comedy at the Golden Globes Awards.
2 Manhattan (1979)
A Writer In New York Tries To Find Love After His Wife Leaves Him
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Manhattan RComedyDramaRomance
Manhattan, directed by Woody Allen, is a romantic comedy-drama that explores the complexities of relationships against the backdrop of New York City. Starring Woody Allen, Diane Keaton, and Mariel Hemingway, the film delves into themes of love, infidelity, and the search for happiness in urban life. Shot in black and white, it’s noted for its iconic imagery and a score featuring Gershwin’s music.
Director Woody Allen Release Date April 25, 1979 Cast Woody Allen , Diane Keaton , Mariel Hemingway , Michael Murphy , Meryl Streep , Anne Byrne Hoffman , Karen Ludwig , Michael O’Donoghue Runtime 96 Minutes
Manhattan is a movie that has a complicated relationship with many fans, thanks to what has happened in the years since it was released. However, taken on its own merits, the film is one of Woody Allen’s best films and one of the best drama movies of the 1970s. Manhattan stars Woody Allen as Isaac, a 42-year-old comedy writer whose second wife left him for a woman. He begins dating a 17-year-old high school student (Mariel Hemingway) and falls in love with his best friend’s mistress (Diane Keaton).
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The idea of Allen casting himself to date a teenager has a very different meaning, considering his future wife, Soopn-Yi Previn, who was 22 when he left Mia Farrow to begin a relationship with her adopted daughter. However, this is a movie that was universally acclaimed, praised by critics with a 93% fresh rating on Rotten Tomatoes, and was added to the National Film Registry by the Library of Congress in 2001.
1 Annie Hall (1977)
A Man Tries To Figure Out The Reason For His Failure To Find Love
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Annie Hall PGComedyDocumentaryRomance
Annie Hall, directed by Woody Allen, stars Allen as comedian Alvy Singer and Diane Keaton as the titular character. The film explores the complexities of relationships through Alvy’s reflections on his romance with Annie, blending comedy and introspective drama. It won multiple Academy Awards, including Best Picture, and is noted for its innovative narrative techniques and sharp dialogue.
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*Availability in US Director Woody Allen Release Date April 19, 1977 Cast Woody Allen , Diane Keaton , Tony Roberts , Carol Kane , Paul Simon , Shelley Duvall Runtime 93 minutes
The best Woody Allen movie of his career came with the 1977 satirical comedy-drama Annie Hall. Allen stars as Alvy Singer, a man who is trying to figure out why his relationship with Annie Hall (Diane Keaton) failed. Allen wrote the part specifically for Keaton to play. While labeled a satire, it fits that role because Allen slightly deconstructs the romantic comedy genre by talking directly to the camera, breaking the fourth wall, and talking to the viewers about what is happening in the movie.
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The film delivers some great comedy moments, but it also takes the story seriously, and what resulted was like nothing in theaters at that time. It ended up a critical breakthrough, with reviews praising Woody Allen’s mastery of writing and directing, with an almost perfect 97% fresh Rotten Tomatoes score. It also won four Oscars, including Best Picture, Best Director, Best Original Screenplay, and Best Actress (Diane Keaton). The Library of Congress added it to the National Film Registry in 1992.