1. The Purple Rose of Cairo (1985)
The Purple Rose of Cairo is a 1985 American romantic fantasy comedy written and directed by Woody Allen, featuring Mia Farrow, Jeff Daniels, and Danny Aiello. Drawing inspiration from films like Sherlock Jr. (1924) and Hellzapoppin' (1941), as well as Pirandello's play Six Characters in Search of an Author, the film follows Tom Baxter, a character who steps out of a fictional movie and into the real world.
Released on March 1, 1985, the film won the BAFTA Award for Best Film, with Allen receiving multiple screenplay nominations, including from the Academy Awards, BAFTA, and the Writers Guild of America. Allen considers it one of his finest films, along with Husbands and Wives (1992) and Match Point (2005).
The Purple Rose of Cairo stands as one of Allen's least conventional works, avoiding the usual neurotic themes and character subversions. It features Mia Farrow and Jeff Daniels in a romantic tale about escaping into fantasy or facing the harshness of reality—a recurring theme in Allen's films, most recently explored in Magic in the Moonlight. However, it is in The Purple Rose of Cairo where this theme is explored with unmatched depth. Allen himself has acknowledged it as one of his best films.
DETAILS:
Release Year: 1985
Genre: Romantic Fantasy Comedy
Director: Woody Allen
Stars: Mia Farrow, Jeff Daniels, Danny Aiello
IMDb Rating: 7.7/10


2. Crimes & Misdemeanors (1989)
Crimes & Misdemeanors is a 1989 American existential comedy-drama written and directed by Woody Allen, starring Martin Landau, Mia Farrow, Anjelica Huston, Jerry Orbach, Alan Alda, Sam Waterston, and Joanna Gleason. The film was widely praised by critics and received three Academy Award nominations: Best Director and Best Original Screenplay for Allen, and Best Supporting Actor for Landau. Many publications have ranked Crimes & Misdemeanors among Allen's best works.
Much like Match Point, the film delves into themes of crime, morality, and justice. It features an outstanding ensemble cast, led by Allen, Martin Landau, Anjelica Huston, Alan Alda, and Sam Waterston.
The story follows Judah Rosenthal, a respected doctor and community leader. As the film opens, Judah is being honored at a party, living a life of luxury in Connecticut, driving a Jaguar, and overseeing the construction of a new wing for the hospital. Throughout the film, Judah grapples with his involvement in the murder of a woman who loves him, a death that occurs not out of passion but for his own convenience.
In this darkest of Allen's black comedies, he not only escapes the consequences of murder but, after a few months, is able to perceive the experience with a strange sense of positivity. If God's eyes are always upon him, what does that say about God?
DETAILS:
Release Year: 1989
Genre: Existential Comedy-Drama
Director: Woody Allen
Stars: Caroline Aaron, Alan Alda, Woody Allen, Claire Bloom, Mia Farrow, Joanna Gleason, Anjelica Huston, Martin Landau, Jenny Nichols, Jerry Orbach, Sam Waterston
IMDb Rating: 7.9/10


3. Blue Jasmine (2013)
Blue Jasmine is a 2013 American drama film written and directed by Woody Allen. The story follows a wealthy and socialite Manhattan woman, played by Cate Blanchett, who becomes homeless and impoverished after her husband is arrested for financial fraud. The film premiered on July 26, 2013, in New York and Los Angeles.
Blue Jasmine received widespread critical acclaim, particularly for Blanchett's performance. The film has also been compared to Tennessee Williams' A Streetcar Named Desire. In addition to its critical success, the film was a commercial hit, grossing $95 million on a budget of just $18 million. Blanchett won the Academy Award for Best Actress, while Sally Hawkins was nominated for Best Supporting Actress and Allen for Best Original Screenplay. Blanchett's portrayal of Jasmine earned her major awards, including a Golden Globe for Best Actress in a Drama, a Screen Actors Guild Award for Outstanding Actress in a Leading Role, and a BAFTA for Best Actress in a Leading Role.
DETAILS:
Release Year: 2013
Genre: Drama
Director: Woody Allen
Stars: Alec Baldwin, Cate Blanchett, Louis C.K., Bobby Cannavale, Andrew Dice Clay, Sally Hawkins, Peter Sarsgaard, Michael Stuhlbarg
IMDb Rating: 7.3/10


4. Hannah And Her Sisters (1986)
Hannah and Her Sisters is a 1986 American comedy-drama film that tells the intertwined stories of a large family over a period of two years, beginning and ending with a Thanksgiving dinner. Written and directed by Woody Allen, the film stars Mia Farrow as Hannah, Michael Caine as her husband, and Barbara Hershey and Dianne Wiest as her sisters.
The ensemble cast also includes Carrie Fisher, Maureen O'Sullivan, Lloyd Nolan (who passed away four and a half months before the film's release), Max Von Sydow, and Julie Kavner. Other notable appearances include Daniel Stern, Richard Jenkins, Fred Melamed, Lewis Black, Joanna Gleason, John Turturro, and Julia Louis-Dreyfus in supporting roles, with Tony Roberts and Sam Waterston making uncredited guest appearances. Several of Farrow's children, including Soon-Yi Previn (who married Allen in 1997), had both credited and uncredited supporting roles, mainly in the Thanksgiving scenes.
Hannah and Her Sisters was Allen's highest-grossing film for many years (adjusted for inflation), with a total North American gross of $40 million. The film won the Academy Award for Best Original Screenplay, Best Supporting Actor, and Best Supporting Actress. It is often regarded as one of Allen's major works, with critics praising its writing and its talented ensemble cast.
DETAILS:
Release Year: 1986
Genre: Comedy-Drama
Director: Woody Allen
Stars: Woody Allen, Michael Caine, Mia Farrow, Carrie Fisher, Barbara Hershey, Lloyd Nolan, Maureen O'Sullivan, Daniel Stern, Max Von Sydow, Dianne Wiest
IMDb Rating: 7.9/10


5. Sleeper (1973)
Sleeper is a 1973 American sci-fi comedy that parodies a bleak future in 2173. Directed by Woody Allen, who co-wrote the screenplay with Marshall Brickman, the film follows a health food store owner who is accidentally cryogenically frozen in 1973 and reawakened two centuries later, only to find himself in a chaotic police state. The movie satirizes contemporary politics and pop culture, paying homage to the classic slapstick comedies of Buster Keaton, Harold Lloyd, and Charlie Chaplin. Many elements of the sci-fi genre are humorously referenced or spoofed.
Among Allen's early and inventive films, Sleeper stands out for its creativity. Set in a dystopian future, the film features Allen’s character who wakes up 200 years later after being frozen against his will. This sci-fi satire with Allen and Diane Keaton was crafted with the intention of being as accurate as possible. To ensure this, Allen and Brickman sent their script to renowned science fiction writer Isaac Asimov for verification.
DETAILS:
Release Year: 1973
Genre: Sci-Fi Comedy
Director: Woody Allen
Stars: Woody Allen, Diane Keaton
IMDb Rating: 7.2/10


6. Love & Death (1975)
Love and Death is a 1975 American comedy written and directed by Woody Allen. This satirical take on Russian literature stars Allen and Diane Keaton as Boris and Sonja, two Russians living during the Napoleonic era, who engage in serious philosophical debates. Allen regarded it as the funniest film he had made up until that point.
Boris, a 19th-century Russian, falls in love with his distant cousin (who is already married) Sonja. Pressed into military service during the war against Napoleon, Boris accidentally becomes a hero before later winning a duel with his cuckolded rival. Upon returning to Sonja, he hopes to settle with her on the steppes, only for her to be consumed by patriotic fervor, insisting that Boris is part of a plot to assassinate Napoleon. His failed attempt leads to his execution by firing squad. After death, Boris appears before Sonja to bid farewell, philosophizes a bit for the audience's benefit, and dances a mazurka with Death.
DETAILS:
Release Year: 1975
Genre: Comedy
Director: Woody Allen
Stars: Woody Allen, Diane Keaton
IMDb Rating: 7.7/10


7. Midnight in Paris (2011)
Midnight in Paris (2011) is a romantic fantasy comedy written and directed by Woody Allen. Set in the enchanting city of Paris, it follows Gil Pender, a screenwriter who is grappling with the unraveling of his relationship with his materialistic fiancée. His life takes a magical turn when, every night at midnight, he travels back in time to the 1920s. The film explores themes of nostalgia and the clash between modernism and the past.
Produced by Spain's Mediapro and Allen's Gravier Productions, the film stars Owen Wilson, Rachel McAdams, Marion Cotillard, Kathy Bates, Léa Seydoux, Carla Bruni, Adrien Brody, and Michael Sheen. It premiered at the 2011 Cannes Film Festival and was released in North America in May 2011. The film received widespread critical acclaim, praised as one of Allen's best works in recent years. In 2012, Midnight in Paris won the Academy Award for Best Original Screenplay and the Golden Globe Award for Best Screenplay. It was also nominated for three other Academy Awards: Best Picture, Best Director, and Best Art Direction. The film was later broadcast on Channel 3 in Spain (with subtitles) and won a Spanish Goya Award, which is equivalent to the Oscar.
DETAILS:
Release Year: 2011
Genre: Romantic Fantasy Comedy
Director: Woody Allen
Stars: Kathy Bates, Adrien Brody, Carla Bruni, Marion Cotillard, Rachel McAdams, Michael Sheen, Owen Wilson, Tom Hiddleston
IMDb Rating: 7.7/10


8. Manhattan (1979)
Manhattan (1979) is a romantic comedy-drama directed by Woody Allen and produced by Charles H. Joffe, with a screenplay by Allen and Marshall Brickman. Allen plays Isaac, a 42-year-old comedy writer who has been divorced twice, is dating a 17-year-old girl (Mariel Hemingway), but finds himself in love with his best friend's mistress (Diane Keaton). The film also stars Meryl Streep and Anne Byrne.
This was Allen's first black-and-white film, shot in a 2.35:1 aspect ratio. The score, which includes George Gershwin's iconic 'Rhapsody in Blue,' greatly influenced the mood and theme of the film. Allen described it as a combination of his earlier film Annie Hall and the more somber Interiors.
The film was well-received by critics, earning Oscar nominations for Best Supporting Actress (Hemingway) and Best Original Screenplay. It grossed $39.9 million in North America, making it Allen's second-highest-grossing film (adjusted for inflation). It ranks #46 on the AFI's '100 Years... 100 Laughs' list and #63 on Bravo's '100 Funniest Movies.' In 2001, the U.S. Library of Congress selected it for preservation in the National Film Registry for its cultural, historical, and aesthetic significance.
DETAILS:
Release Year: 1979
Genre: Romantic Comedy-Drama
Director: Woody Allen
Stars: Woody Allen, Diane Keaton, Michael Murphy, Mariel Hemingway, Meryl Streep, Anne Byrne
IMDb Rating: 7.9/10


9. Match Point (2005)
Match Point is a psychological thriller from 2005, written and directed by Woody Allen, starring Jonathan Rhys Meyers, Scarlett Johansson, Emily Mortimer, Matthew Goode, Brian Cox, and Penelope Wilton. The plot follows Rhys Meyers' character, who marries into a wealthy family but faces social ruin after embarking on an affair with his brother-in-law's girlfriend, played by Johansson. The film explores themes of morality, greed, and the role of desire, money, and luck in life. Many critics have compared it to Allen's earlier film Crimes and Misdemeanors (1989). Produced and shot in London due to financial difficulties in New York, Allen rewrote the screenplay to shift the setting from New York to London, using primarily a British cast and crew.
Critics in the United States praised the film's return to form and its British setting, while reviews in the UK were less favorable, criticizing the choice of locations and the use of British idioms in the dialogue. Allen was nominated for an Academy Award for Best Original Screenplay.
DETAILS:
Release Year: 2005
Genre: Psychological Thriller
Director: Woody Allen
Stars: Brian Cox, Matthew Goode, Scarlett Johansson, Emily Mortimer, Jonathan Rhys Meyers, Penelope Wilton
IMDb Rating: 7.6/10


10. Annie Hall (1977)
Annie Hall is a 1977 American romantic comedy-drama directed by Woody Allen, based on a screenplay he co-wrote with Marshall Brickman. The film stars Allen as Alvy Singer, a man trying to understand the reasons behind his failed relationship with the woman he loved, played by Diane Keaton, in a role tailor-made for her.
Filming began on May 19, 1976, on Long Island’s South Fork and continued intermittently over the next ten months. Allen described the film as a major turning point in his career, marking his first collaboration with cinematographer Gordon Willis. Unlike his earlier comedies, this film introduced a more serious tone. Scholars have noted the contrast between the urban environments of New York City and Los Angeles, the exploration of gender roles and sexuality, Jewish identity, as well as elements of psychoanalysis and modernism.
Annie Hall premiered at the Los Angeles Film Festival on March 27, 1977, before its official U.S. release on April 20, 1977. The film received critical acclaim and was nominated for the Big Five Academy Awards, winning four: Best Picture, Best Director for Allen, Best Original Screenplay for Allen and Brickman, and Best Actress for Keaton. Additionally, the film won four BAFTA Awards and a Golden Globe, the latter awarded to Keaton. The film grossed $38,251,425 in the U.S. and Canada, ranking fourth among Allen's films when adjusted for inflation.
Regarded as one of the greatest films ever made, it ranks 31st on AFI’s list of the 100 Greatest American Films, 4th on the list of 100 Funniest Films, and 28th on Bravo’s “100 Funniest Movies.” Film critic Roger Ebert described it as “Woody Allen’s favorite film of all time.” The screenplay was named the funniest ever written in the Writers Guild of America’s “101 Funniest Screenplays” list. In 1992, the U.S. Library of Congress selected the film for preservation in the National Film Registry for its cultural, historical, and aesthetic significance.
DETAILS:
Release Year: 1977
Genre: Romantic Comedy-Drama
Director: Woody Allen
Stars: Woody Allen, Diane Keaton, Tony Roberts, Carol Kane, Paul Simon, Janet Margolin, Shelley Duvall, Christopher Walken, Colleen Dewhurst
IMDb Rating: 8.0/10


