Iconic Films: ‘Annie Hall’: Woody Allen’s Best Ever

May 15, 2020 Updated: May 15, 2020

PG | | ComedyRomance | 20 April 1977 (USA)

“Annie Hall” won four Oscars at the 50th Academy Awards in 1977, including for best picture, beating out “Star Wars.” This is Woody Allen’s signature film and masterpiece, and definitely his most popular.

It’s also one of the best films of the 1970s, and underlines Allen’s quintessential niche—that of a (self-proclaimed) New York, Coney Island-raised, Jewish working-class-background nebbish-y comic, whose self-deprecating neurosis is born of Jewish guilt combined with an autodidactic, college professor-level intellectualism. Even though the man claims to prefer watching the Knicks and playing his clarinet, he clearly read his way through most of New York’s Strand Bookstore.

“Annie Hall” is also a love letter to Diane Keaton (her unique, Chaplinesque feminist wardrobe started its very own fashion craze) and is Allen’s romanticized version of New York City existence, which was only topped by his next film, “Manhattan.”

Mostly, “Annie Hall” is not a conventional romantic comedy. It’s a very accurate and bittersweet depiction of the dynamics of relationships, tinged with Allen’s melancholic personality, and made to go down easier than it normally would, due to his world-class humor.

Odd Couple

woman and man on park bench in "Annie Hall"
Annie Hall (Diane Keaton) and Alvy Singer (Woody Allen) in “Annie Hall.” (United Artists)

Alvy Singer (Woody Allen) meets Annie Hall (Dianne Keaton) after a doubles tennis match arranged by his friend Rob (Tony Roberts). She’s a ditzy Wisconsinite WASP trying to make it as a singer in New York, and he’s a Jewish schlemiel of a New York comedian.

Their relationship initially works because Annie is starry-eyed and naïve, and Alvy is established and exotic to her and has much to teach her. He turns her young, curious mind on to many things, including books on death and dying, college courses, therapy, and black-and-white documentaries about the Holocaust.

Annie and Alvy move in together, and we soon observe the vast, cultural Grand Canyon between their two families (Annie’s grandmother, “Grammy Hall,” is rabidly anti-Semitic).

Annie then slowly begins to blossom as a recording artist, which takes her to Los Angeles, wooed away by Paul Simon (of Simon and Garfunkel) playing an L.A. agent. Alvy, ever the dedicated New Yorker, makes one feeble attempt to woo her back.

Paul Simon in bar scene in "Annie Hall"
Paul Simon (C) and Diane Keaton (R) star in “Annie Hall.” (United Artists)

Impressions 45 Years Later

Watching it all these years later, what jumps out at me is how incredibly self-involved Alvy is. Mostly, we think of Keaton’s Annie Hall as a vacuous, “la-dee-dah” airhead, but at this late date, her character seems like a perfectly normal, uneducated, low-self-esteem-having small-town girl, with Alvy Singer buzzing around her like a horsefly.

He’s forever landing on her with the quick stings of invasive insight into her character flaws that only a professional stand-up comedian could get away with, because the stings are leavened with humor. But seeing it now, I’m amazed she didn’t start trying to swat him earlier. Not to mention the slightly creepy, fumbling foreplay he’s forever foisting. Overall hangs the slightly pornographic atmosphere emanating from his obvious obsession with sex.

Speaking of which, all Alvy’s women were, or are, in therapy, and they’re there because he makes them go (and pays for their therapy himself), because he always wants sex, and his mechanical, cerebral approach and overly verbose nebbish-y commentary makes them all (highly unsurprisingly) never in the mood. Annie would like to smoke weed all the while, and Alvy doesn’t like that—he’d like for her to appreciate him for who he is, but he’s too annoying and icky to be appreciated without chemical enhancement.

And I never noticed before (until I had an acting career of my own) what a great job Diane Keaton did. She’s pretty brilliant. No wonder she’s had such showbiz longevity.

Lastly

man and woman in a kitchen in "Annie Hall"
Annie Hall (Diane Keaton) and Alvy Singer (Woody Allen) in “Annie Hall.” (United Artists)

“Annie Hall” was also highly innovative for its time, utilizing subtitles to express characters’ subtexts, as well as an animated sequence. Allen constantly addresses the camera directly, such as when, standing in line to see an Ingmar Bergman film, he’s subjected to the excruciating torture of a pseudo-intellectual blowhard behind him trying to impress a date. The man waxes poetic about the failures of Fellini and name-drops Marshall McLuhan. When Allen can’t take it anymore, he pulls the actual McLuhan out of thin air in the lobby, who flatly informs the pompous blowhard, “You know nothing of my work.” “Why can’t this happen in real life?” Allen asks us.

3 men in a movie theater ticket line in "Annie Hall"
(L–R) Russell Horton, Woody Allen, and Marshall McLuhan star in “Annie Hall.” (United Artists)

All in all, “Annie Hall” is really a brilliant depiction of the generation, stasis, degeneration, and destruction phases of a relationship. It’s so often the case that relationships don’t work out because women think they can change men (men never change; men represent order), and men think women will stay the same (women change and evolve quickly; women represent chaos).

Annie Hall outgrows Alvy. She reads his intellectual books, takes his prescribed adult education courses, puts together her own worldview, sheds her naïveté, grows up, and, not being nearly as neurotic (and with a woman’s natural pragmatism and common sense in matters of the heart) recognizes that he’ll never change, will never learn to have fun, and will project his neurotic neediness onto her forever. And so she moves on. It’s perfect. And sad. And funny. Re-rent it.

man and woman seated in a restaurant in "Annie Hall"
Alvy Singer (Woody Allen) and Annie Hall (Diane Keaton) star in “Annie Hall.” (United Artists)

‘Annie Hall’
Director: Woody Allen
Starring: Woody Allen, Diane Keaton, Carol Kane, Paul Simon, Shelley Duvall, Colleen Dewhurst, Christopher Walken, Tony Roberts
Rated: PG
Running Time: 1 hour, 33 minutes
Release Date: April 20, 1977
Rated: 4.5 stars out of 5

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