1. Annie Hall (1977)

IMDB Rating: 8/10
RottenTomatoes Rating: 98%

Storyline: Annie Hall is a film about the on-and-off relationship between neurotic New York comedian Alvy Singer (played by Allen himself) and the ditzy Annie Hall (Diane Keaton). Woven from Allen’s personal experiences, the film recounts their relationship in retrospect, exploring topics of love, neurosis, and the human condition in the process. It is a story of craving for companionship and the painful realization of the imperfections that can end a relationship.

Why It’s A Major Movie: Winning the academic recognition of winning four Academy Awards including Best Picture, Best Director, Best Original Screenplay, and Best Actress for Diane Keaton, Annie Hall established Woody Allen as a serious auteur. A major departure from the slapstick comedies that made Allen’s name, Annie Hall is a movie of great emotional depth, philosophical insight and famously innovative narrative structure.

Why It’s A Major Movie: From a cinematic standpoint, “Annie Hall” broke from the traditional linear narrative structure to adopt a more fragmented, impressionistic form. This innovative storytelling, added with the memorable performances, great dialogues and Allen’s typical New York humor and neuroticism gave the movie its own unique identity. Importantly, it is a film that, while making viewers laugh, makes them reflect on their own life and relationships.

2. Manhattan (1979)

IMDB Rating: 7.9/10
RottenTomatoes Rating: 97%

Storyline: In “Manhattan,” Woody Allen plays Isaac Davis, a divorced, middle-aged man dating Tracy (Mariel Hemingway), a 17-year-old girl. However, Isaac grows infatuated with Mary (Diane Keaton), the mistress of his best friend, leading to complications. The film brilliantly showcases New York City in ways that highlight the neurotic, insecure, and beautifully flawed characters played to perfection by its cast.

Why It’s A Major Movie: The excellence of “Manhattan” lies in Allen’s ability to combine hilarious comedy with profound sentiments about age, time, and love. The film is shot in stunning black-and-white by cinematographer Gordon Willis, and coupled with a Gershwin score, it became iconic for visually rendering Allen’s love for the city. It showcases Allen’s ability to portray New York City not just as a backdrop, but as a living, breathing character.

Why It’s A Major Movie: “Manhattan” is also noted for intelligent dialogue, sharp wit, and nuanced performances. It is a testament to Allen’s talent as a filmmaker who uses his personal experiences and cinematic inspirations to deliver a beautiful film about love, infidelity, and friendships. Allen’s clever screenplay, strikingly beautiful cinematography, and standout performances strike a balance that solidifies “Manhattan” as one of his most celebrated films.

3. Hannah and Her Sisters (1986)

IMDB Rating: 7.9/10
RottenTomatoes Rating: 93%

Storyline: Centered on a trio of sisters and their complicated relationships with each other and the men in their lives, “Hannah and Her Sisters” is an intimately woven tale of love, infidelity, and the search for happiness. Star-studded with performances from Barbara Hershey, Dianne Wiest, and Mia Farrow as the eponymous sisters, the film spans three Thanksgiving dinners to dissect and explore the dynamics and complexities of human relationships through Woody Allen’s unique lens.

Why It’s A Major Movie: “Hannah and Her Sisters” is a testament to Woody Allen’s knack for writing strong female characters that are as complicated as they are relatable. It brought together an impressive ensemble cast, who delivered some truly unforgettable performances, especially Wiest and Caine who won Academy Awards for Best Supporting Actress and Actor respectively. The film enjoys a place amongst the finest dramedies of American cinema, showcasing Allen’s directorial prowess in balancing comedy and drama.

Why It’s A Major Movie: The film reflects Allen’s mastery over emotional nuances and storytelling, by effortlessly oscillating between the sisters’ lives, their interactions, and their individual stories. Apart from being a well-made film, it also deepens Allen’s exploration of his beloved New York, painting an upper-middle-class Manhattan with sharp, vibrant strokes.

4. Midnight in Paris (2011)

IMDB Rating: 7.7/10
RottenTomatoes Rating: 93%

Storyline: “Midnight in Paris” narrates the soul-searching journey of romantic screenwriter Gil Pender (Owen Wilson) who, while on a vacation with his fiancee Inez (Rachel McAdams), discovers a fantastical way of travelling back in time to the 1920s Paris. Meeting profound artists and writers like Ernest Hemingway, F. Scott Fitzgerald, and Gertrude Stein, Gil embarks on an enchanting exploration of nostalgia, disillusionment, and ultimately, love.

Why It’s A Major Movie: “Midnight in Paris” garnered universal acclaim for it’s strong narrative, likeable characters, and a theme that speaks to the nostalgic romantic in all of us. It sees Allen returning to the romantic comedy genre with his wit and charm intact, making it his highest-grossing film in North America. The film’s screenplay won the Academy Award, marking a late-career highlight for the filmmaker.

Why It’s A Major Movie: Despite being a light-hearted whimsical journey, Allen successfully weaves in profound elements of existential anxieties, human ideals, and the illusion of the “Golden Age.” The beautiful depiction of Paris, an exceptional cast, and clever writing triggering laughter and introspection at the same time, makes it an essential watch for Allen enthusiasts and general audiences alike.

5. Crimes and Misdemeanors (1989)

IMDB Rating: 7.9/10
RottenTomatoes Rating: 93%

Storyline: “Crimes and Misdemeanors” is a profound exploration of morality and the human condition. The film weaves two parallel stories: one of a successful ophthalmologist who contemplates murder to escape from an inconvenient affair, and the second of a downtrodden documentary filmmaker who is infatuated with his brother’s assistant.

Why It’s A Major Movie: The movie is cherished for Allen’s ability to blend deep moral questions with humor and show how crimes can go unpunished in real life—highlighting stark realities and the complex nature of morality and justice. “Crimes and Misdemeanors” is considered a major movie for Allen as it showcases his depth as a writer and director, weaving in philosophical and existential inquiry into a narrative that is accessible and entertaining.

Why It’s A Major Movie: Allen’s direction, the strong performances, especially by Martin Landau and Allen himself, the cinematography by Sven Nykvist, and Allen’s ability to emotionally and intellectually captivate the audience make it one of the best films in his oeuvre.

6. The Purple Rose of Cairo (1985)

IMDB Rating: 7.7/10
RottenTomatoes Rating: 91%

Storyline: “The Purple Rose of Cairo” is a magical realism film that tells the story of Cecilia (Mia Farrow), a depression-era waitress who finds solace in watching films. The lines between reality and celluloid blur when a dashing fictional character, Tom Baxter (Jeff Daniels), breaks the fourth wall and steps out of the movie screen, changing Cecilia’s life forever.

Why It’s A Major Movie: This film is a metafilmic love letter to cinema’s power to transport us into a world of fantasy and provide a refuge from grim realities. A departure from Allen’s more grounded New York dramas, the magical reality of ‘Purple Rose’ illustrates his range as a director and his unique ability to blend the mundane and the fantastical.

Why It’s A Major Movie: “The Purple Rose of Cairo” is a commentary on the complex relationship between art and life; it explores the disillusionment of reality and the allure of escapism. This film’s poignant, imaginative exploration of this theme has cemented it as one of Woody Allen’s masterpieces.

7. Match Point (2005)

IMDB Rating: 7.6/10
RottenTomatoes Rating: 78%

Storyline: “Match Point” is a dramatic thriller that follows Chris Wilton (Jonathan Rhys Meyers), a former tennis pro, who becomes entangled in the lives of a wealthy family and ensnared in a web of infidelity and deceit with fatal consequences. Themes of ambition, lust, guilt, and luck are masterfully intertwined in this film noir with a twist.

Why It’s A Major Movie: “Match Point” marked Woody Allen’s first departure from his typical New York-based films, providing a fresh, darker, intriguing perspective to human relationships and morality in the setting of upper-class London. Acclaimed for its twist-filled narrative, the film is also celebrated as one of Allen’s boldest ventures into the genres of thriller and drama.

Why It’s A Major Movie: The intense performances, particularly by Scarlett Johansson and Jonathan Rhys Meyers, coupled with the film’s biting commentary on class and ambition, have made it a staple in Allen’s filmography. It marked a revival in Allen’s career and is frequently cited as his most engrossing and suspenseful film to date.

8. Zelig (1983)

IMDB Rating: 7.7/10
RottenTomatoes Rating: 100%

Storyline: “Zelig” depicts the story of Leonard Zelig (Woody Allen), an anomaly of the 1920s, who possesses the uncanny ability to transform himself to resemble anyone he’s around. Using mock-documentary style, Allen presents an allegorical tale about human conformity and need for acceptance combined with cutting-edge special effects of the era.

Why It’s A Major Movie: “Zelig” stands out in Woody Allen’s filmography for its pioneering use of mockumentary style and technical excellence in incorporating Allen’s character into archival footage. This film is a classic example of Allen’s creativity and inventiveness, pushing the boundaries of traditional storytelling methods while spotlighting his comedic genius.

Why It’s A Major Movie: The film’s perfect blend of humor and deep social commentary cemented its place as a pioneering work in mockumentary filmmaking. Its universal appeal lies in the brilliance of its concept, the originality of the screenplay, and Allen’s commitment towards creating a unique visual experience, making it a must-watch for cinephiles and comedy lovers alike.