Life Lessons From Woody Allen: His Top 10 Movie Quotes

From the risqué and the rude to the profound and the life-affirming, Woody Allen’s best film quotes represent a snapshot into the human condition from the perspective of a chaotic mind constantly questioning the meaning of his own existence.

That he finds a way to turn fallibility, vulnerability and failure into hilarious screen stories that speak volumes about life, relationships, love, romance and sex, showcases the genius of the man.

Woody Allen’s best movie quotes

Woody Allen has been making a movie a year since 1969. This means that more than any other filmmaker this side of the studio system, he has developed a production line relationship with movies, seeing them no longer as tortuous endeavours, rather, aside from being commodities he can deliver with precision and utmost efficiency, they’re a sort of catharsis, a self-run psychological assessment.

Year after year we see how Woody Allen has dealt with his obsessions: relationships, existentialism, New York City, mortality and the movies, often revisiting them on infinite occasions, as if trying to find a deeper truth.

Using self-deprecating humour, artistic elitism and fast paced, slapstick dialogue he is one of the few modern American filmmakers who has earned the “auteur” label. You can always tell when you’re watching a Woody Allen movie.

10. “Sex without love is an empty experience but as empty experiences go, it’s one of the best.”

Love and Death (1975)

Love and Death is still considered one of Woody Allen’s best films. On Rotten Tomatoes, a consensus of critics reveals collective applause for Allen’s ability to mix his neurotic persona into a Tolstoy pastiche. It remains one of his funniest films and features many of his best quotes including “Sex without love is an empty experience but as empty experiences go, it’s one of the best.”

9. “I think crime pays. The hours are good, you meet a lot of interesting people, you travel a lot.”

Take the Money and Run (1969)

A 1969 American mockumentary comedy, Take the Money and Run introduced audiences to the delights of Woody Allen. He co-wrote the screenplay with Mickey Rose and stars alongside Janet Margolin in a film that chronicles the life of inept bank robber Virgil Starkwell.

8. “What a world. It could be so wonderful if it wasn’t for certain people.”

Radio Days (1987)

Radio Days saw Allen earn himself yet another Oscar nomination for Best Original Screenplay but has found itself a little lost amongst the many delights of his eighties output.

This was the decade of Hannah and Her Sisters, The Purple Rose of Cairo, Broadway Danny Rose, Zelig and Crimes and Misdemeanors – all great films.

Radio Days is slighter than anything of these, but more than makes for it in charm. Essentially, it builds on the flashbacks to Alvy Singer’s youth in Annie Hall.

The setting is the mid-forties (the golden age of the radio) and the structure a loose compendium of scenes and sketches in a manner that recalls, as Roger Ebert stated at the time, Fellini’s Amarcord.

There’s plenty of wit and plenty of warmth too, making this one of Allen’s most inviting works. It’s also the only film of his to feature both Mia Farrow and Diane Keaton, though not onscreen at the same time.

7. “I was thrown out of NYU for cheating on my Metaphysics final. I looked within the soul of the boy sitting next to me.”

Annie Hall (1977)

Annie Hall marked Woody Allen’s first step as a cinematic force of nature and the conflicts behind its creation are best conveyed in all the title changes it went through.

Coming from a strictly comedic background made this dramedy an extremely risky choice in Allen’s career and he tried to balance its content with the audiences’ perception of him by calling it either It Had to be Jew or Rollercoaster Named Desire.

Ultimately Allen chose to simply name it after its lead character (played by Diane Keaton), a ditzy but lovable woman who falls in love with Allen’s character, Alvy Singer.

The film chronicles their stormy relationship and is juxtaposed with Alvy’s memories and anecdotes (some of which have the parodic content of his previous directorial efforts) making it the perfect combination of drama and comedy.

Annie Hall has the always self-deprecating director open his heart to audiences instead of hiding behind the safety mask of laughter, the result being something that borders on magic realism.

The complexity of romantic relationships has rarely been dissected with such bittersweet precision and the screenplay’s quotability has made it an essential element of popular culture, to the point where we might wonder how people dealt with heartbreak before Annie Hall.

6. “The most beautiful words in the English language aren’t ‘I love you’ but ‘it’s benign.’”

Deconstructing Harry (1997)

A great Woody Allen quote in a mediocre Woody Allen film. Deconstructing Harry sees its central plot focusing on a successful writer named Harry Block, played by Allen, who is driving to a university from which he was once thrown out, in order to receive an honorary degree.

He’s accompanied by three passengers: a prostitute, a friend, and his son, whom he has kidnapped from his ex-wife. Their experiences are mixed with flashbacks, segments taken from Block’s writing, and interactions with his own fictional characters.

5. “The important thing, I think, is not to be bitter. You know, if it turns out that there IS a God, I don’t think that He’s evil. I think that the worst you can say about Him is that, basically, He’s an underachiever.”

Love and Death (1975)

In 1975, Woody Allen considered Love and Death the funniest film of his career thus far. Film critic Gene Siskel agreed, saying at the time: “Woody Allen is simply terrific in ‘Love and Death.’ To my mind, it’s his funniest film. He plays to his greatest strength (gag line dialogue) and stays away from what has limited his other movies (an attempt to develop a story).”

In this comic take on 19th-century Russian philosophical novels as well as epic Soviet-era films, Allen’s Boris, a simple Russian villager who pines from afar for his beautiful cousin Sonja (Diane Keaton), is forced against his will into joining the Russian army during the Napoleonic Wars.

Surprisingly, the cowardly Boris becomes a military hero. But when his beloved Sonja comes to him with a dangerous patriotic scheme in the film which arrived between Sleeper (1973) and Annie Hall (1977), Boris and Sonja embark on mock-serious philosophical debates.

4. “When it comes to sex there are certain things that should always be left unknown, and with my luck, they probably will be.”

Everything You Always Wanted to Know About Sex* (*But Were Afraid to Ask) (1972)

Woody Allen’s 1972 sex comedy anthology consists of a series of short sequences loosely inspired by the 1969 book of the same name by David Reuben.

The 10th highest-grossing film of 1972, Everything You Always Wanted to Know About Sex* (*But Were Afraid to Ask) was one of Allen’s biggest early-career box office hits.

Film critic Christopher Null called it a “minor classic and Woody Allen’s most absurd film ever”. The film was initially banned in Ireland. A cut version was passed eventually passed six years later following the removal of both a bestiality reference (“the greatest lay I ever had”, referring to a sheep) and a man having sex with a bread loaf.

3. “There are worse things in life than death. I mean, if you’ve ever spent an evening with an insurance salesman, you’ll know exactly what I mean.”

Love and Death (1975)

Originally meant to be a film about two New Yorkers who discover their neighbour murdered someone, Love and Death only came into fruition when Allen reached a creative block in his project and distracted himself with a book on Russian history.

The result was the finest film of his early comedic era: a parody of Russian literature in which the main characters (played by Allen and his then muse Diane Keaton) discuss existentialism as they plot to kill Napoleon.

Every scene is a delight and the film’s overall bittersweet tone announced what was coming next in his career. Oh and when he finally got to making the movie about the New Yorkers, almost twenty years later, it was the fantastic Manhattan Murder Mystery.

2. “Don’t knock masturbation – it’s sex with someone I love.”

Annie Hall (1977)

There’s simply no denying it, Woody Allen’s most popular film is also one of his best. I’ve had the tendency to talk myself into dumbing Annie Hall down; convince myself that it isn’t as good as it is. Then, of course, I watch it and am reminded of its genius.

I want to draw particular attention to something I don’t think gets mentioned enough in Annie Hall discussions, and that’s the film’s seamless shift of narratives. There is animation, black and white, colour; the fourth wall is broken, narration is used, then abandoned; the timeline is linear, until it’s not, and so on.

I know a few people who have been putting this movie off because they think they know what they’re in for. How wrong could they be?

1. “Last time I was inside a woman was when I visited the Statue of Liberty.”

Crimes and Misdemeanors (1989)

Woody Allen’s 1989 comedy-drama film sees the writer-director star alongside Martin Landau, Mia Farrow, Anjelica Huston, Alan Alda, Sam Waterston, Jerry Orbach, Claire Bloom and Joanna Gleason.

The story follows two strands. The first involves Judah Rosenthal (Landau), a successful and reputable ophthalmologist, and the second focuses on Clifford Stern (Allen), a small-time documentary filmmaker.

Landau’s Judah is a philandering eye doctor who wants to preserve his marriage. His brother Jack (Orbach) comes up with what appears to be the only viable solution. Certain that his mistress (Huston) is about to reveal their affair to his wife (Bloom), Judah agrees to Jack’s murderous plan.

Twinned with Judah’s tale in this three-time Oscar-nominated film is that of Cliff Stern, a documentary filmmaker whose problems, which involve love and art, are tame but funny.

Roger Ebert, in his glowing review in the Chicago Sun-Times, wrote: “The movie generates the best kind of suspense, because it’s not about what will happen to people—it’s about what decisions they will reach.

“We have the same information they have. What would we do? How far would we go to protect our happiness and reputation? How selfish would we be? Is our comfort worth more than another person’s life? Allen does not evade this question, and his answer seems to be, yes, for some people, it would be.”

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