Retrospective: Is "Annie Hall" Still the King of Rom-Coms?

It has, perhaps, aged poorly, but Woody Allen's iconic romantic comedy still has quite a lot to offer.

May 21, 2023

In the Fall of 1982, San Diego attorney Dan Broderick hired former flight attendant Linda Kolkena as his legal assistant. He was 38 and married with four kids. She was 21. It was typical for a slick-haired lawyer: hiring a young bombshell to bend over the desk while the wife kept the home afloat. It was bad enough that Dan had leeched off her to complete law and medical school, but now he had committed the ultimate betrayal. Dan moved out of the family home in 1985, and he and Linda married in 1989, four years after he filed for divorce from his wife, Betty, who equated the drawn-out divorce to “putting a housewife in the ring with Muhammad Ali.”

Dan wasn't just a lawyer: he was President of the San Diego Bar Association. He had the strings and could pull them at his discretion.

Betty claimed Dan used his status in the legal community to impede her from finding representation, sell their home out from under her, and take her share of the marital assets. According to her, Linda even mailed her face creams and fat loss ads.

Soon, Betty became unhinged. She dumped her children off at Dan and Linda's house one by one, left hundreds of incendiary messages on their answering machine, and even drove her car through the front of their home despite the children's presence inside.

By any measure, Dan won the divorce. Betty was in shambles, alone and without the affection or comforts she had once known. Dan lived the high life, having traded in his wife for a younger model while retaining his career and social status.

It wouldn’t do.

Early on November 5, 1989, Betty used her daughter’s key to the new Broderick home. With the Smith and Wesson revolver she’d purchased months before, she snuck into the bedroom and shot Dan and Linda, killing both.

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The exact events of that morning will forever be a mystery, as will the full extent of the Brodericks’ marital woes, which only adds to the mystique. For pseudo-feminist apologists, Betty is an abuse victim whose life imprisonment is not a punishment that fits the crime. No one questions Dan’s role in the marital breakdown and Betty's sorrow, but behind Betty’s eyes is something profound. It is not her psychosis, although the cold emptiness is palpable. It is not a woman who’s changed her account of the murders so many times she’s diminished all credibility. It is instead a simple truth:

Breaking up is hard to do.

Enter Alvy Singer, the flawed protagonist of Woody Allen’s landmark 1977 romantic comedy, Annie Hall. He is a chatterbox neurotic with a penchant for finding the dark side, an everyman in all the concepts he makes himself a victim of but entirely unto himself in all the specific ways he lives as that victim.

Alvy is a conversationalist, as much with us as his in-film audience. The man speaking with Annie in a movie theater line, lamenting the pretentiousness of a nearby cinephile, is no different from the one who starts the film talking to the camera about his life. We still sense his neuroses, panic, and the vague intellectualism that masks countless insecurities.

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We always feel attached to him as we behold the failures he wants to understand, but in a way that makes us ache for him to know right from wrong the way we think we do. Every time he veers left, we scream to bear right. Every time he zigs, we beg for him to zag. We are alike enough to see the path, which makes his inability to walk it frustrating and humorous.

But in that opening is the answer Alvy seeks. He is a man whose personality, hopscotching from one idea to the next while roping everything under the same umbrella, is initially charming. It endears us to him and makes us just as curious about the mechanics of his doomed romances as he is. As the movie progresses, we become irritated. The charm fades: what once seemed like intellect and cleverness feels like insecurity and paranoia. In the end, he is no different from anyone else.

We cannot always be to people as we were in the beginning. Sparks are fleeting: a flame can only get achieved if one catches. Most times, they don’t. The reasons why are many and dependent on the people, their circumstances, timing, even setting. The difference? We can, with time, accept that. Alvy cannot.

Annie Hall has us instantly gain the measure of the man while insisting on spinning through the cycle of his failed relationships, making it as intriguing as annoying. Something is there about how we fail to improve and insist upon ourselves despite the diminishing returns, but simply because something is true to life does not mean we need to see it.

Thankfully, when Annie Hall measures itself, it works. It understands that two people need not be fascinating individually to be compelling together. Annie wants to sing and dress in her own style, but nothing distinguishes her (though, in fairness, that was groundbreaking in 1977). Alvy is a man of fixations and rationalized pessimism, but nothing separates him from your garden-variety neurotic.

It knows that these are the people whose interactions are fascinating. It is not pitting royalty against poverty or thrusting two beautiful people into extraordinary circumstances that intrigue us, but how the minor things play off one another. It is how a man fearful of everything charms a free spirit in his desperation to evade a lobster but erodes her affections the more often he applies that anxiety. It is divvying up the assets, gently revisiting the same frustrations that ended the relationship while trying to part civilly. Alvy and Annie’s chemistry is sincere because it is quiet. Although our affections feel fiery, they are hushed. We develop interests and passions, but building depth is a subdued enterprise.

It knows that a comedy can never be so realistic that it forgets to be a movie and make us laugh. Life isn't funny. It has funny moments, but on its own, it lacks humor: Annie Hall creates that humor with stylistic quirks. It flashes back to Alvy’s youth and breaks the fourth wall as he relates to us, pondering the fate of our grade school classmates and the mixed results, some in exact alignment with our predictions and others throwing us for a loop. It reflects on the mother who wanted us to follow the other good children and stop thinking for ourselves. It cuts to a cartoon of us bickering with a lover, always employing extremes to validate our point.

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It hits what we’re all thinking as we try to impress a potential partner, masking what we mean with the same attempts at repartee foreign to our personality and aims at intellectualism we know we don’t possess. It knows the pain of enduring a pretentiousness in a line from which there's no escape and how badly we wish we could shatter the pomposity. It knows we all think we’re good drivers and make awkward small talk as we dance around our intentions, throw out jokes that don’t land, and pretend to like the stories of people we hate.

When Annie Hall knows us, it’s great. When it uses its true-to-life form to excuse self-indulgence as it drags on longer than necessary, it is not.

Once we riddle out failure, dwelling on it is cumbersome. It drags us down, stagnates us, and prevents us from reaching our full potential. Annie Hall riddles out the failure of Alvy’s relationships quickly and thus ceases to be necessary. Everything past that is an exercise in pointlessness.

Annie Hall is funny but not hilarious; it is knowledgeable but not profound; it is a human experience that transcends nothing. Thus, when it exhausts its purpose, it crashes and burns.

In the end, however, it does something few films do: fulfill its purpose. It shows us why Alvy’s relationships failed but, by doing so, shows why ours have too. It shows us how we succeed in building bonds and all the pointless tests we put them through without realizing. It shows how to ruin something great while explaining why what we wanted was a bad fit. It shows that although we may never completely put the past behind us, we can move on.

Perhaps if Betty Broderick’s defense team had shown Annie Hall to the jury, she would be a free woman. Can we not see the struggles of maintaining relationships? Can we not process the spiritual trials of withstanding such loss and betrayal? We understand. It’s not her fault. As Alvy and Annie show us, breaking up is hard to do.