The best of Woody Allen: Five films every movie fan should watch

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Woody Allen is a prolific filmmaker, actor, and comedian whose career spans over six decades. Known for his unique blend of humour, philosophy, and romantic storytelling, Allen has crafted films that explore the complexities of love, identity, and the human experience. His distinctive style often features neurotic characters navigating the intricacies of relationships, all set against vibrant urban backdrops. With a filmography that includes numerous classics, Allen has solidified his place as one of the most influential directors in cinema.

Today we would like to explore his top five films, ranked from fifth to first, to celebrate this visionary director's remarkable work. So let's not waste any more time. Here's what we consider to be the best of Woody Allen.

5. Hannah and Her Sisters (1986)

Hannah and Her Sisters revolves around the lives of three sisters—Hannah (Mia Farrow), Lee (Barbara Hershey), and Holly (Dianne Wiest)—over the course of two years. The film explores their romantic entanglements, personal struggles, and the complexities of family relationships, all set against the backdrop of New York City.

This film is a brilliant exploration of love, loss, and the interconnectedness of human relationships. Allen masterfully weaves together multiple storylines, showcasing how the characters' lives intersect and influence one another. The film's witty dialogue and sharp observations on life and love make it a poignant reflection on the nature of happiness and fulfillment. With strong performances from the ensemble cast, Hannah and Her Sisters stands as a testament to Allen's ability to blend humour with deep emotional insights.

4. Annie Hall (1977)

Annie Hall is a romantic comedy that follows the relationship between neurotic comedian Alvy Singer (Woody Allen) and the quirky, free-spirited Annie (Diane Keaton). The film explores the ups and downs of their relationship, filled with humour, introspection, and memorable moments.

This film is often considered one of Allen's masterpieces, showcasing his unique storytelling style and innovative narrative techniques. Annie Hall breaks the fourth wall and employs flashbacks, voiceovers, and animated sequences to convey the complexity of love and relationships. It offers a candid look at the intricacies of romance, capturing both the joyous and painful aspects of falling in love. With its sharp wit and relatable characters, Annie Hall has become a quintessential romantic comedy that continues to resonate with all of us.

3. Vicky Cristina Barcelona (2008)

Set in Spain, Vicky Cristina Barcelona follows two American women, Vicky (Rebecca Hall) and Cristina (Scarlett Johansson), as they embark on a summer of self-discovery and romantic entanglements. Their lives become intertwined with the passionate artist Juan Antonio (Javier Bardem) and his volatile ex-wife María Elena (Penélope Cruz).

This film is a captivating exploration of desire, passion, and the complexities of relationships. Allen beautifully captures the allure of Barcelona and the intoxicating nature of love, showcasing how different characters experience and interpret passion. While Vicky Cristina Barcelona holds a personal appeal for me (placing it third in my rankings), I acknowledge that Annie Hall offers a more refined cinematic experience in terms of storytelling and character development. Nevertheless, this film remains a delightful exploration of romance and self-discovery.

2. Midnight in Paris (2011)

Midnight in Paris follows screenwriter Gil Pender (Owen Wilson) as he travels to Paris with his fiancée, Inez (Rachel McAdams). While exploring the city at night, Gil mysteriously finds himself transported back to the 1920s, where he meets his literary and artistic idols, including Ernest Hemingway and F. Scott Fitzgerald.

This film is a whimsical exploration of nostalgia, creativity, and the allure of the past. Allen skillfully blends fantasy with reality, capturing the magic of Paris and the longing for a bygone era. Midnight in Paris resonates with all of us on a personal level, as it beautifully encapsulates the idea that we often romanticise the past while overlooking the beauty of the present. The film's clever dialogue, stunning cinematography, and delightful performances make it my favourite Woody Allen film, showcasing his ability to evoke emotion through humour and charm.

1. Manhattan (1979)

Manhattan is a romantic drama that follows Isaac Davis (Woody Allen), a twice-divorced television writer, as he navigates his relationships in New York City. The film is shot in black and white, capturing the city's timeless beauty while exploring themes of love, ambition, and the search for meaning.

From a cinematic perspective, Manhattan is Allen's crowning achievement, showcasing his mastery of visual storytelling and character development. The film's stunning cinematography, paired with a brilliant score by George Gershwin, creates a romantic and nostalgic atmosphere that resonates with all of us. Allen's exploration of love, art, and the complexities of human relationships is both poignant and relatable. While I personally cherish Midnight in Paris as my favourite, I can't help but appreciate Manhattan as a more profound and influential cinematic work, solidifying Allen's status as a unique voice in modern cinema.

And that's all for today! Woody Allen's films are characterised by their wit, introspection, and exploration of the human experience. From the humorous complexities of Annie Hall to the enchanting nostalgia of Midnight in Paris, Allen's work captures the nuances of love, relationships, and personal identity. His ability to blend humour with profound insights ensures that his films remain relevant and cherished by audiences around the world. Each of these top five films showcases a different facet of his artistic vision, reflecting both personal preferences and the rich cinematic legacy he has created.

Now we would love to hear about your experiences with Woody Allen's work! Which of his films do you consider the best? Would you rearrange the list or add any others? We can't wait to read your thoughts in the comments!