Woody Allen has a lot of work in his filmography, considering he has written and directed a movie every year since the early 70s, and about half of them are dramas and the other half are comedies.
While some of his films are dark and brooding and heavily influenced by Ingmar Bergman, there are still a handful of timeless comedies that can produce a chuckle out of even the most severe critics.
1. Take the Money and Run
This film is Allen’s first directing, writing, and starring credit in his filmography, and “Take the Money and Run” is unlike all of his movies that would come later, considering that it was all presented in the form of a mockumentary. The film centers on Virgil Starkwell (Woody Allen), who wants to become a notorious bank robber. Virgil does not exactly succeed because he is completely incompetent.
The film features “interviews” with the people in Virgil’s life, including his wife Louise (Janet Margolin). Louise delivers one of the movie’s funniest lines: “He is always very depressed. I think that if he’d been a successful criminal, he would have felt better. You know, he never made the ‘10 most wanted’ list. It’s very unfair voting; it’s who you know.” The movie is incredibly silly, but it features Allen’s goofy sense of humor that would develop and mature over the years.
This film is equally as silly as “Take the Money and Run” and just as absurd. In “Bananas”, Fielding Mellish (Allen) is drafted as the leader of the turbulent country of San Marcos after he falls in love with one of the resistance fighters named Nancy, played by his then-wife Louise Lasser, who he divorced in 1970. Fielding dons an obviously fake beard and becomes the revolutionary leader in order to win the heart of Nancy.
The film is riddled with Allen’s signature one-liners, one of the best being: “We fell in love. I fell in love – she just stood there.”
3. Everything You Always Wanted to Know About Sex * But Were Afraid to Ask
This film was “inspired” by Dr. David Reuben’s book “Everything You Always Wanted to Know About Sex”, though the film is far from clinical. The movie is made up of seven segments that are supposed to be based on Reuben’s book.
The answers to the questions are equally ridiculous and incredibly juvenile, but this type of old school alternative comedy would eventually make its way into the mainstream. The scenarios are outrageous, including one with Allen and a large group of actors playing sperm, and a giant breast rolling through the countryside.
The film also features the late great Gene Wilder, which is more than enough reason to watch it. Though most of the comedic lines are risqué, one of the best clean one-liners is when Allen plays a medieval fool who says, “Before you know it, the Renaissance will be here and we’ll all be painting.”
4. Love and Death
This satirical film is Allen’s take on 19th-century Russian literature and the Soviet-era epic films that inspired them. Allen plays a Russian villager named Boris who pines from afar for his beautiful cousin Sonja (Diane Keaton).
This is the second film in which the two starred together, the first being “Play It Again, Sam”, a severely underrated film written by Allen and directed by Herbert Ross. In “Love and Death”, Boris is forced to join the Russian army during the Napoleonic Wars, and similarly to “Bananas”, he accidentally becomes a military hero. Boris and Sonja’s paths cross again and they try to assassinate Napoleon.
This movie is full of comedic bits, but the best is when Boris’ uncle is holding a small bit of dirt and Allen says: “In addition to our summer and winter estate, he owned a valuable piece of land. True, it was a small piece, but he carried it with him wherever he went.” After so much silliness, it’s hard to believe what would come next.
5. Annie Hall
This film would eventually become widely regarded as Allen’s best and most iconic film and it even earned him four Oscars. “Annie Hall” centers on the comedian Alvy Singer, played by Allen, who talks about his difficulties with love, marriage, and intimacy and also about his failed relationship with Annie (Diane Keaton). Though the film is sometimes heartbreaking and dramatic, it still manages to maintain a comedic sensibility.
The film seems so far removed in its honesty, but Allen’s unique brand of comedy still appears in the lighter parts of the film, such as the famous scene that involves the two of them trying to cook live lobsters, and it sometimes emerges in some of the bleaker moments, up until the last joke that compares relationships to eggs.
There are too many great lines to pick just one, but one of the best is when Annie notices there’s no trash on the streets of Los Angeles, to which Alvy replies: “That’s because they don’t throw their garbage away, they turn it into television shows.”