Comedy films often get disrespected when compared to dramas. Because of their lighter tone and less consequential themes, comedies are stereotyped as easier to make and less integral in developing movies as a medium. Woody Allen is one of the pioneers in changing the perception of the comedy genre. Understanding that humor is the backbone of being human, Allen has made an entire filmmaking career out of laughs.
Woody Allen started his career as a standup comedian before transitioning to movie-making in the 1960s and 1970s. His movies dissect the differences between men and women, what motivates people in relationships, and the messiness of intersecting occupational and personal dramas. Much like Clint Eastwood, Allen starred in and directed most of his best films simultaneously. These are the best Woody Allen movies ranked for your viewing pleasure!
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10. Another Woman (1988)
Gena Rowlands and Mia Farrow (perhaps Allen’s favorite collaborator) are empowering and inspirational in this underrated drama that Woody Allen wrote and directed but didn’t act in. Another Woman discusses female regret through the eyes of a middle-aged woman (portrayed by Rowlands) as the university professor realizes her life is unfulfilling despite achieving career success. Marion Post believes many of her struggles resemble those of a therapy patient she hears from afar (played by Farrow). Themes such as living in the present and overcoming the past work incredibly well here to make this a Woody Allen movie with a lot of heart and soul.
9. Vicky Cristina Barcelona (2008)
96m
Genre
Drama, Romance
Stars
Scarlett Johansson, Rebecca Hall, Javier Bardem
Directed by
Woody Allen
Watch on Tubi
One of the newer films on this list, Vicky Cristina Barcelona leverages the beauty of its titular setting and outstanding performances from Scarlett Johansson and Penélope Cruz to make for a memorable summertime romp. Javier Bardem is at the center of a love rectangle as his wife and two other women are all fighting for his desires. The female focus of the film is a trademark of Woody Allen movies, but the lighter tone than some of his earlier tragic stories separates it from others.
8. Midnight in Paris (2011)
94m
Genre
Fantasy, Comedy, Romance
Stars
Owen Wilson, Rachel McAdams, Kathy Bates
Directed by
Woody Allen
Watch on Amazon
Woody Allen dives headfirst into the fantasy genre in this early 2010s story of a man who travels back to the 1920s repeatedly and each time learns a little more about love and himself. The references to art and French culture in the 20th century make Midnight in Paris a special experience for history buffs and hopeless romantics alike. Kathy Bates and Owen Wilson are awesome performers here.
7; The Purple Rose of Cairo (1985)
82m
Genre
Fantasy, Comedy, Romance
Stars
Mia Farrow, Jeff Daniels, Danny Aiello
Directed by
Woody Allen
Watch on Tubi
Mia Farrow plays a woman who gets the gift of dating her biggest movie crush while navigating the trials of her real relationship. Allen uses the fantasy genre here to great effect by manifesting one of life’s greatest daydreams. We all imagine dating our favorite celebrities and stars, and The Purple Rose of Cairo illustrates the pleasures and downfalls of making those illusions tangible.
6. Blue Jasmine (2013)
99m
Genre
Drama
Stars
Alec Baldwin, Cate Blanchett, Louis C.K.
Directed by
Woody Allen
Watch on Amazon
Cate Blanchett astounds in this thought-provoking film about an upper-class woman who succumbs to personal and professional turbulence. The massive divide between rich and poor is expertly examined when Blanchett’s character must lower her standards and live with her sister in an environment she isn’t used to. Allen’s dedication to depicting women’s multifaceted struggles during different time periods in his career remains his enduring legacy, and Blue Jasmine is a crown jewel of that trademark.
5. Interiors (1978)
93m
Genre
Drama
Stars
Geraldine Page, Kristin Griffith, Mary Beth Hurt
Directed by
Woody Allen
Watch on Amazon
Interiors takes the time to reflect on the effects of divorce and marital separation throughout an entire family of adults when Arthur and Eve go their separate ways. The couple’s three daughters all react differently to the split, and the plot digs into sibling dynamics and mental health problems as an outcome of parental relationship problems. Diane Keaton is one of the headlining actresses in Woody Allen’s first drama movie that forgoes all comedic elements.
4. Bullets Over Broadway (1994)
98m
Genre
Comedy, Crime
Stars
John Cusack, Chazz Palminteri, Dianne Wiest
Directed by
Woody Allen
Watch on Tubi
Bullets Over Broadway applies dark comedic undertones to significant results with a funny mobster storyline that also underlines the outside influences of show business. John Cusack is a playwright who makes the unfortunate decision to seek financial help from the mob without realizing he would be beholden to the boss’s whims when writing his script and casting his actors. Dianne Wiest won an Academy Award for this film.
3. Hannah and Her Sisters (1986)
107m
Genre
Comedy, Drama
Stars
Woody Allen, Michael Caine, Mia Farrow
Directed by
Woody Allen
Watch on max
Perhaps Woody Allen’s best family drama is Hannah and Her Sisters. Starring himself among many talented, usual collaborators, the film captures the zaniness of the average American family in New York City. Holiday traditions and the stress of the season wrap the romantic and family issues in a nice bow. Julia Louis-Dreyfus and Carrie Fisher are excellent yet underrated here.
2. Manhattan (1979)
96m
Genre
Comedy, Drama, Romance
Stars
Woody Allen, Diane Keaton, Michael Murphy
Directed by
Woody Allen
Watch on Amazon
Manhattan possesses some outdated plot points (Allen’s character is romantically involved with a 17-year-old in the film), but the filmmaking techniques remain indelible to the genre. Allen plays a divorcee who wanders through his early 40s, not exactly knowing what he’s seeking. The use of New York’s wide setting, black and white cinematography, and nostalgic yearning for a love that may not exist make it an intimate but ominous romance film.
1. Annie Hall (1977)
93m
Genre
Comedy, Drama, Romance
Stars
Woody Allen, Diane Keaton, Tony Roberts
Directed by
Woody Allen
Watch on Tubi
Woody Allen’s magnum opus, Annie Hall, remains the romantic comedy most think of when they hear his name. Allen plays a defeatist New Yorker who daydreams of his what-if romance with the titular woman, played by Diane Keaton. The plot and themes are similar here to all of Woody Allen’s movies, but it feels like every element was humming to perfection, even compared to other films on the list. Annie Hall won the Academy Award for Best Picture over the first Star Wars film.
