Essential Woody Allen Movies to Watch in the Holiday Season

The holiday season is a good time of the year to rewatch some Woody Allen movies.

Allen is one of the most recognizable Hollywood directors thanks to his unmistakable sophisticated style. After making his directorial debut with 1966’s What’s Up, Tiger Lily?, Allen explored the dramas of mid-upper-class people. Over the years, the New Hollywood wave director received much recognition from the cinematographic industry, taking home four Academy Awards, among a plethora of other accomplishments. In his more-than-50-year-long career, Allen has worked with all of Hollywood’s major actors and actresses with noticeable results. He also directed several appreciated movies, getting critical approval and the audience’s favor. Now, the highly-regarded New York City-born artist has recently blown 87 candles. His upcoming project is a noir comedy titled Wasp 22 is currently in production in Paris, France.

Here is a list of some of the best Woody Allen movies to watch.

Annie Hall (1977)

Arguably, the best Woody Allen movie and one of the best films ever made. Allen was the jack of all trades in the movie he directed, wrote, and also acted in, one of the first times the director enacted his classic neurotic character tormented by endless existential questions in front of the camera. The Academy rewarded Allen (who started his long tradition of never attending the Oscars on that occasion) with the Awards for Best Script, Direction, and Best Picture. His muse, Diane Keaton, took home the prize for Best Actress.

Manhattan (1979)

Together with Annie Hall, the best movie directed by Allen. Manhattan is an ode Allen wrote to his home city, a love letter to the place where he grew and developed as an artist. The iconic Manhattan opening still stands today as one of the best ways to begin a story in medias res. Once again, Allen starred in his own film and joined forces with Keaton, who portrayed the mistress of a divorced comedy writer’s best friend (Michael Murphy). The Manhattan cast included Mariel Hemingway, Meryl Streep, and Anne Byrne. The movie picked up three Oscar nominations, including Best Original Screenplay.

Hannah and Her Sisters (1986)

Hannah and Her Sisters is another excellent example of Allen’s directorial style and witty writing. The story follows a family and their dramas and misadventures over the span of two years. The ensemble cast featured Allen himself, Michael Caine, Mia Farrow, Carrie Fisher, Barbara Hershey, Lloyd Nolan, Dianne Wiest, and Maureen O’Sullivan, among others. Hannah and Her Sisters mesmerized audiences, critics, and insiders, ultimately taking home three Academy Awards, including Best Supporting Actor for Caine and Best Supporting Actress for Wiest.

Bullets Over Broadway (1994)

As time went by, Allen appeared less in front of the camera in his own movies and let different actors portray a slightly different version of Allen himself. That was the case of John Cusack in this 1994 crime comedy, where he acted as David Shayne, an idealistic playwright desperately looking to finance his own play. Bullets Over Broadway landed seven Oscar nominations — on a par with Hannah and Her Sisters for the most in Allen’s career — and allowed Dianne Wiest to land her second Best Supporting Actress Academy Award. The cast included Jim Broadbent, Harvey Fierstein, Chazz Palminteri, and Mary-Louise Parker.

Midnight in Paris (2011)

One of the best Woody Allen movies of the new millennium is Midnight in Paris. The Academy Award-winner original story follows Gil Pender (a majestic Owen Wilson), an American writer who happens to spend some time in Paris before his wedding with his obnoxious fiancée (Rachael McAdams). When the sun goes down, magic comes to life in the City of Light. Thanks to an ingenious time machine, Gil meets F. Scott Fitzgerald, Ernest Hemingway, Salvador Dalí, and many other intellectuals of the Belle Époque. Allen paid homage to some of his literary idols by displaying his idea of what Paris meant for the world during the Roaring Twenties. The cast also featured Kathy Bates, Adrien Brody, Carla Bruni, Marion Cotillard, and Michael Sheen, among others. The movie was quite successful and earned more than $154 million, Allen’s biggest box-office success to date.