Most people don't like Olive Kitteridge. Not at first, anyway. She’s the kind of woman who’d scold you for breathing too loudly in a library or judge your choice of curtains without blinking. If you saw her walking down a street in Crosby, Maine, you’d probably cross to the other side just to avoid the inevitable prickly comment. Yet, the HBO series Olive Kitteridge managed to turn this seemingly unreachable, "unlikeable" woman into one of the most deeply human characters ever put on screen.
Honestly, it shouldn't have worked. A four-part miniseries about a depressed, aging math teacher in a quiet coastal town? On paper, it sounds like a recipe for a very long nap. But instead, it became a powerhouse. It swept the Emmys in 2015, taking home eight awards including Outstanding Limited Series.
The secret sauce wasn't just the source material—Elizabeth Strout’s Pulitzer Prize-winning novel—but the fact that Frances McDormand basically willed this thing into existence. She bought the rights to the book before it even won the Pulitzer. She knew. She saw something in Olive that most of us are too afraid to look at in ourselves.
What Most People Get Wrong About Olive
There is a common misconception that Olive is just a "mean old lady" or a "curmudgeon." That’s a lazy way to look at her. Olive isn't mean for the sake of being mean; she’s a woman who has no filter for the "inanities" of life. She views the world with a stark, brutal honesty that most of us mask with politeness and "nice" talk.
You’ve probably met an Olive.
Maybe she’s your aunt who tells you your haircut is a mistake right before Thanksgiving dinner. Or the teacher who never gave out an A because "perfection doesn't exist." In the show, Olive’s husband, Henry (played with heartbreaking warmth by Richard Jenkins), is her polar opposite. He’s the town pharmacist. He’s "nice." He hands out greeting cards and smiles at everyone.
The friction between them is the heartbeat of the series. Henry’s kindness often feels like a performance to Olive, a way to paper over the deep, dark wells of depression that run through their family and their town. Olive doesn't paper over anything. She sits in the dark.
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The Maine of It All
The setting isn't just a backdrop. It’s a character. The fictional town of Crosby is beautiful but cold. Director Lisa Cholodenko and cinematographer Frederick Elmes captured that specific New England light—the kind that makes everything look crisp but also a little lonely.
The series spans 25 years. We see the seasons change, and we see the characters sag under the weight of time.
It’s not a "fast" show. It’s a slow burn. If you’re looking for high-octane drama or "who-done-it" twists, you’re in the wrong place. The "action" in the HBO series Olive Kitteridge consists of things like:
- Planting tulip bulbs.
- Buying a box of chocolates.
- A son's wedding that goes awkwardly wrong.
- A terrifying, random encounter at a hospital that changes nothing and everything.
Why the Structure Matters
The show is divided into four distinct parts: "Pharmacy," "Incoming Tide," "A Different Road," and "Security." Each one jumps forward in time. This is where the adaptation actually gets really smart. In Elizabeth Strout's book, the stories are "linked"—sometimes Olive is the lead, sometimes she’s just a shadow in someone else’s story.
The HBO version centers her more firmly. This makes the experience more intimate, almost uncomfortably so. You are stuck with her. You feel her resentment toward her son, Christopher, and you feel her silent, complicated grief when things don't go the way she expected.
One of the most powerful scenes—and I think about this a lot—is in the second episode. Olive encounters a former student, Kevin Coulson (Cory Michael Smith), who has returned to town with plans to end his life. Olive doesn't give him a Hallmark-style pep talk. She doesn't tell him "it gets better." Instead, she sits in the car with him and talks about her own father's suicide.
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She meets him in the hole. That’s her superpower. She can’t do "nice," but she can do "real."
That Bill Murray Cameo
By the time we get to the final episode, "Security," Olive is older, lonelier, and grappling with the "ultimate existential question." Enter Jack Kennison, played by Bill Murray.
Murray plays a wealthy, grieving widower who is just as much of a mess as Olive is. Their chemistry is weirdly perfect. It’s not a late-in-life romance in the traditional sense. It’s two survivors of life’s "messiness" bumping into each other and deciding that maybe, just maybe, being alone is worse than being with someone who is equally difficult.
"The world baffles me," Olive tells him.
"It baffles me too," Jack replies.
That’s basically the thesis of the whole show.
The Legacy of the "Unlikeable" Woman
Before the HBO series Olive Kitteridge, we didn't see many women like this on TV. We had "difficult" men like Tony Soprano or Don Draper, but women were usually expected to be the nurturers or the villains. Olive is neither. She is a mother who loves her son but also makes him feel small. She is a wife who loves her husband but can’t bring herself to be "sweet" to him.
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It’s a masterclass in nuance. Frances McDormand’s performance is so vanity-free it’s almost startling. She lets the camera see every wrinkle, every frown, every moment of pure, unadulterated annoyance.
Does it hold up in 2026?
Absolutely. If anything, the show feels more relevant now. We live in an era of curated lives and "toxic positivity." Olive Kitteridge is the antidote to that. She reminds us that life is often disappointing, people are complicated, and depression isn't something you just "get over" with a morning yoga routine.
It’s a story about the stamina it takes to stay decent in a world that feels increasingly fragmented.
Actionable Takeaways for Your Watch List
If you haven't seen it, or if you're planning a rewatch, here is how to get the most out of the experience:
- Don't binge it too fast. This isn't a show to power through in one sitting. Give each of the four episodes space to breathe. The time jumps are significant, and you need a moment to process how the characters have aged and changed between segments.
- Pay attention to the "minor" characters. Actors like Jesse Plemons, Rosemarie DeWitt, and Peter Mullan pop up in small but vital roles. Their stories provide the context for Olive’s world.
- Watch for the silence. Some of the best moments in the series happen when no one is talking. Watch McDormand’s face when she’s alone in her kitchen or tending her garden.
- Read the book afterward. Elizabeth Strout’s prose is a different kind of magic. The show is an incredible adaptation, but the book offers deeper insights into the other residents of Crosby that the miniseries had to trim for time.
Basically, the HBO series Olive Kitteridge is a reminder that even the most difficult people have a pulse. It’s a quiet, beautiful, and sometimes devastating look at what it means to grow old and realize that you never quite figured it all out. And honestly? That’s okay.
Start with Episode 1 tonight. Don't expect to love Olive immediately. Just let her be who she is. By the time Bill Murray shows up in the finale, you might just find yourself wishing you could sit on a park bench with her, too.