Annie Hall

Alvy Singer and Annie Hall share a quiet moment in Annie Hall (1977)

“‘I would never want to belong to any club that would have someone like me for a member.’ That’s the key joke of my adult life, in terms of my relationships with women.”

Clever movies are a bit of a dying art. Nowadays, studios keep things pretty simple so nothing flies over the heads of their audience. Annie Hall, written and directed by Woody Allen (Crimes and Misdemeanors, Manhattan) and starring Woody Allen and Diane Keaton, is a film that’s clever to a fault. Some have said this is the greatest romantic comedy of all time, but I disagree—it’s not perfect, but that’s kind of the point Allen is trying to make. Much like the lead character Alvy, the film is smart and funny, but can be a bit condescending and has trouble connecting with people. This film was somewhat autobiographical for Allen, but he doesn’t romanticize his quirks and neuroses—he shows how they can be endearing, but also how they can be destructive. Overall, the film is intelligent, witty, and surprisingly deep in some spots, filling an odd void in the cinema world: admitting that it’s possible to be too smart for your own good.

The plot follows Alvy Singer, a sarcastic and bitter comedian in New York, as he meets Annie Hall, a free-spirited woman who understands and appreciates Alvy’s intelligence. Past that, the plot itself is pretty loose, showing the ups and downs of Alvy and Annie’s relationship as the find comfort in their connection while getting frustrated with their differences. The film is more about answering the question of what romance really means than about a neat plot, so monologues and little scenes between Annie and Alvy make up the bulk of the movie.

A relationship, I think, is like a shark. You know? It has to constantly move forward or it dies. And I think what we got on our hands is a dead shark.

Writer and director Woody Allen is known for his witty humor, but up until this film came out, he had never gotten deep and personal. As we see Alvy and Annie struggling to connect with each other, buried in that story is Allen’s own struggle to connect with the world. Alvy’s intelligence shines through even his silly moments, but underneath it all is a subtly depressing statement: being intelligent can be really isolating and lonely. This film is intelligent in its humor, but few films have dared to make that depressing statement so blatantly. But in its brutal honesty, it captures a frustration many of us brainy people have felt so often in life.

Alvy, in a white shirt and pants, talks to Annie Hall, in a loose-fitting shirt, vest, and tie.
Annie Hall’s clothes in this film caused a bit of a fashion outrage. Fun fact: They were Diane Keaton’s own clothes.

The film itself is not overtly depressing—it’s actually really funny. There’s a great comedic chemistry between the two leads, and many times I found myself laughing even though a joke was not extremely funny—the execution was just that good. Parts of this film are Alvy’s fantasy of how he wished the world worked, and the film is not afraid to break the fourth wall to get this point across. There are also some pretty deep references to some more obscure thinkers and artists that were nice to see, even if a few went over my head.

I won’t say Annie Hall is the funniest movie ever made, but it’s definitely one of the smartest comedies ever made. Thankfully, this film’s intelligence and earnestness were recognized when it won the Oscar for best picture (beating out Star Wars!) in 1977. The film has some pretty frank discussion of relationships and sexuality which will go over the heads of younger audiences. But if you’ve ever felt isolated by your own intelligence or if you just wish comedies were a little smarter, this will be a movie you love.

View my complete list of classic, essential, or just plain good movies!

Runtime: 1:33
Director: Woody Allen
Year: 1977
Genres: comedy, romance
Rating: PG

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