This Top 5 is devoted to listing the best Woody Allen films. Emerging out of film school, I enthusiastically went on a mission to watch the complete Allen filmography, interspersing his films amongst my various Netflix selections, but I quickly discovered and soon enough grew tired of his formula of exploring the lives of stuffy intellectuals that are obsessed with love, infidelity, and death. My motivation for the mission has lapsed, but I do recognize a few significant blind spots that I need to catch up with, including The Purple Rose of Cairo and Everything You Wanted to Know About Sex* (But Were Afraid to Ask). So, without claiming the mantle of Allen expert and with a relatively small pool to pull from, here is my attempt at the best Woody Allen films.

Gibelwho Productions Top 5 Woody Allen Films:

5. Match Point

4. Scoop

3. Hannah and Her Sisters

2. Manhattan

1. Annie Hall

Match Point (2005): This film makes the list purely by being so distinctive amongst Allen’s other works. It is a dark exploration of lust, greed, and deception, with a double murder thrown into the mix. Although it focuses on the upper crust, typical for Allen, it features an outsider who is faking his way through society and who avoids retribution for his infidelity. I didn’t love this film, but it certainly showed that Allen had some range.

Scoop (2006): His follow-up film to Match Point and continuing his collaboration with Scarlett Johansson, Allen took a completely different tact and focused on a romantic comedy aesthetic, with an additional murder mystery bent. The Woody Allen film persona that was so refined in the 1970s and 80s has transitioned quite nicely into Johansson’s fretful father figure. This film has a metaphysical element as well that heightens the comedy, as ghosts appear throughout the story to move the plot along and the film is bookended by scenes on the barge of death, a device pulled from Greek mythology. A brisk plot and entertaining interactions between Johansson and Allen earn this film a place on the list.

Hannah and Her Sisters (1986): Here the “Woody Allen’s persona” is presented in full force. When surrounded by a cast of white, upper class characters, he pops and shines with his witty dialogue and hypochondriac obsessions. This is the quintessential Allen film, with the kooky Woody character, a terrific ensemble, and a story that explores his favorite topics of infidelity and death; it almost seems like all other Allen films are trying to recapture what this film has in spades.

Manhattan (1979): The jazz, the Gershwin, the loving gaze of the camera that reveals New York City in its finest. Woody’s most artistic cinematic achievement is filled with his same themes of love, infidelity, and obsession with death. This all comes together in the first scene, a series of shots that feature the structures of New York, with Gershwin’s Rhapsody in Blue filling the soundscape, and the voiceover narration that (perhaps unintentionally) reveals the nature of Woody’s writing and thus film career. Continually mulling over the same themes, approaching them from subtly different angles, working through the less than stellar miss-steps, and refining his approach until finally the music booms and he produces a combination of words and images that are a triumph.

Annie Hall (1977): While this may be the typical choice when ranking Allen’s films, this movie was my first introduction to the filmmaker and his persona, so it was still new, and not fatigued. The formal elements of the film managed to surprise me at every turn, including the sequences of animation, the stream of consciousness monologues that directly address the camera, interactive flashbacks to his childhood that feature quirky characters, the sub-titles expressing the inner monologues that overlay the awkward early relationship conversations. It was a fresh voice that turned the romantic comedy genre on its head and ultimately deserves the title of masterpiece.