The 10 Most Underrated Woody Allen Movies, Ranked (From Least to Most Underrated)

Woody Allen’s filmography spans several decades and moves through different cities, eras, and genres. He made features in New York and abroad, worked with cinematographers such as Gordon Willis, Sven Nykvist, Carlo Di Palma, Darius Khondji, Zhao Fei, and Vittorio Storaro, and often used preexisting jazz recordings instead of original scores. Across comedies, dramas, and experiments in form, he returned to subjects like chance, identity, morality, and show business while shifting tones from playful to somber.

This list presents ten of his films that often sit outside the most cited titles. The selections cover black and white experiments, ensemble comedies, somber character studies, and late career entries set in London and on the American coast. Casts include Oscar winners and international stars, and many of the productions were financed by European partners and released by specialty distributors in the United States.

‘You Will Meet a Tall Dark Stranger’ (2010)

Set in London, the story follows an older man who abruptly leaves his wife, a struggling writer who becomes infatuated with a neighbor, and a gallery employee whose employer faces financial strain. The plot connects these characters through fortune telling, romantic missteps, and professional setbacks across neighborhoods, offices, and apartments in the city.

The film features Anthony Hopkins, Gemma Jones, Naomi Watts, Josh Brolin, Antonio Banderas, Freida Pinto, and Lucy Punch. It was shot on location in London with a production partnership that included European financing, and it was released domestically by a specialty label in the United States.

‘Wonder Wheel’ (2017)

Set in 1950s Coney Island, the film centers on a waitress who lives with her carousel operator husband and whose life is disrupted when his daughter arrives on the run. A lifeguard who narrates from the beach observes the personal and family conflicts that unfold beneath the amusement rides and boardwalk lights.

Kate Winslet, Justin Timberlake, Juno Temple, and Jim Belushi lead the cast. Vittorio Storaro photographed the production with a stylized use of color and practical lighting to evoke period signage and interiors, and the release came through a distributor that partnered with a streaming company on the rollout.

‘Celebrity’ (1998)

The film follows a writer who chases celebrity profiles and parties while his ex wife builds a new life after their divorce. Shot in New York, the story moves through magazine offices, film sets, fashion events, and hotel suites as characters cross paths with models, actors, and producers.

Kenneth Branagh and Judy Davis star, with appearances by Leonardo DiCaprio, Charlize Theron, Winona Ryder, and Melanie Griffith. Sven Nykvist shot the film in black and white, and it premiered at major fall festivals before a theatrical release by a specialty distributor.

‘Melinda and Melinda’ (2004)

Two parallel versions of one premise unfold at a dinner table as storytellers imagine a woman arriving at a small gathering. One thread plays as a comedy and the other as a drama, and the film alternates between the two tracks while keeping the same core characters and situations.

Radha Mitchell plays the title role in both versions, with Will Ferrell, Chiwetel Ejiofor, Amanda Peet, and Chloë Sevigny among the ensemble. It was filmed in Manhattan with interiors and street locations, and its release was handled by a specialty label known for independent and international titles.

‘Cassandra’s Dream’ (2007)

Set in contemporary London, two brothers facing money problems accept a dangerous job from a wealthy relative. The assignment tests their loyalties and changes their relationships with family members and partners as they move between pubs, marinas, and suburban streets.

Colin Farrell and Ewan McGregor star alongside Tom Wilkinson, Hayley Atwell, and Sally Hawkins. The score is by Philip Glass, and the production shot around London and coastal areas before releasing in multiple territories through independent distributors.

‘Irrational Man’ (2015)

A philosophy professor arrives at a New England college and becomes close to a student while befriending a fellow faculty member. The plot turns on an ethical decision that takes shape during a casual conversation at a diner and ripples through classrooms, wooded campuses, and seaside neighborhoods.

Joaquin Phoenix, Emma Stone, and Parker Posey lead the cast. Darius Khondji served as cinematographer, the film shot around Rhode Island and Massachusetts, and the United States release was handled by a specialty outfit with a focus on arthouse fare.

‘Small Time Crooks’ (2000)

A group of would be robbers rents a storefront to cover a plan to tunnel into a bank vault. When the cover business selling cookies becomes unexpectedly popular, the crew shifts from crime to entrepreneurship and then to the challenges of sudden wealth.

Woody Allen stars with Tracey Ullman, Hugh Grant, Elaine May, Michael Rapaport, and Jon Lovitz. Zhao Fei was the cinematographer, production took place in New York City, and DreamWorks Pictures released the film in theaters in North America.

‘Shadows and Fog’ (1991)

Set in a European town with winding streets and foggy nights, the story follows a timid clerk who is caught up in a search for a murderer. The action weaves through a circus troupe, boarding houses, and police stations as the town mounts an overnight manhunt.

The ensemble includes Woody Allen, Mia Farrow, John Malkovich, Madonna, and Donald Pleasence, with cameos by several well known actors. Carlo Di Palma shot the film in black and white on large sets built at Kaufman Astoria Studios, and the production incorporates music associated with Kurt Weill to match its expressionist style.

‘Another Woman’ (1988)

A professor rents a quiet office to finish a book and begins overhearing therapy sessions through a vent in the wall. The accidental eavesdropping leads her to reconsider choices from her past while interacting with family members, friends, and former colleagues.

Gena Rowlands plays the lead, with Mia Farrow, Ian Holm, Gene Hackman, Blythe Danner, and Harris Yulin in supporting roles. Sven Nykvist was the cinematographer, New York City locations provide exteriors and interiors, and the film was released by a specialty distributor after a festival premiere.

‘Zelig’ (1983)

Presented as a mock documentary, the film profiles a man who assumes the appearance and behavior of people around him and becomes a media curiosity. The narrative places interviews and newsreels alongside staged material to trace his rise, treatment, and romance across late 1920s and early 1930s New York.

Woody Allen and Mia Farrow star. Gordon Willis photographed the film using period lenses and photochemical techniques to combine new footage with archival material, and the production team created vintage costumes and sets to match historical newsreels. The film received multiple award nominations for its technical achievements.

Share your picks for overlooked titles and tell us which films you would add in the comments.