Jessica Woodville | Memoir & Musings

The Struggle of Choosing Just One Favorite Movie

Whenever someone asks me, “What’s your favorite movie?” I freeze. Not because I don’t have one, but because I have too many. How do you choose between the movies that shaped you, the ones that comfort you, and the ones that completely wreck you in the best possible way? My favorites shift depending on my mood, my memories, or even the time of year. Some movies make me laugh when I need levity, others make me cry when I need release. Some transport me back to childhood, while others remind me of who I’ve become.

If there’s a pattern to my favorites, it’s that I’ve always been drawn to movies that blend the fantastical with deep emotion—films that don’t just entertain but immerse you. Stories that make you feel something real. Whether it’s magic, nostalgia, comedy, or heartbreak, the movies I return to again and again are the ones that offer a sense of comfort, a familiar escape, or even a way to process emotions I don’t have words for.

Looking back, my favorite films act like mile markers along the road of my life—evidence of the phases I went through, the things I longed for, and the emotions I struggled to articulate. So, instead of picking just one, I want to explore the movies that have meant the most to me over the years, and what they might say about the person I am today.

From Fantasy to Heartache: Some Films That Have Stayed With Me

It shouldn’t surprise me that the movies that come to mind first when asked about my favorites are stories filled with magic and wonder. From an early age, I was drawn to films that weren’t just visually stunning but emotionally complex—stories that stirred something deep within me (which of course was partially a deep desire to be kidnapped by faeries).

Legend and Labyrinth were staples in my childhood, movies my father and I watched over and over. They were mesmerizing, filled with beauty and darkness, light and shadow—something an empath like me picked up on even then. My father also introduced me to The Last Unicorn, always telling me I was “the last unicorn in a world that had forgotten magic.” I had almost forgotten that until now. It feels significant, looking back—how, after all I had already survived and before everything else I would go on to endure, my father instilled in me the belief that magic and light still existed in this world. Perhaps it was because he was starting to lose his own.

As a millennial, I have a lifelong, healthy obsession with Disney. Beauty and the Beast spoke to my bookish nature and dreams of one day having a library as grand as the Beast’s. The Little Mermaid resonated with my hopeless romantic side, and it didn’t help that my cousins used to call me Ariel because of the reddish hue in my brown hair. Sleeping Beauty always takes me back to watching it with my grandpa after he’d get home from the graveyard shift at the prison. He’d start lightly snoring, and I’d innocently wake him up to ask if he was asleep. “No, just resting my eyes…” he’d mumble before the gentle snores continued.

Then there was Hercules—my first visual introduction to the mythology my father had told me as bedtime stories long before I was old enough to read. Even as a kid, I recognized that Disney had taken some hilarious creative liberties (Zeus, a kind and loving father? Sure.) But I loved it all the same. Ferngully was another early favorite, an environmentalist fairytale that probably helped shape the little hippie heart I didn’t realize I had at the time.

Movies were an escape when real life was too heavy.

As I got older, my movie tastes evolved just as life itself does in those strange, in-between teenage years. I started falling in love with cult classics like Empire Records and Hackers, both of which I could probably still recite word for word. I found comfort in Adam Sandler movies, particularly Billy Madison, which I can definitely still quote from start to finish. When life felt overwhelming, I turned to comedy—whether it was Adam Sandler, Jim Carrey, or the kind of absurd humor that let me momentarily forget everything else.

But I also found Robin Williams.

At first, he was just the voice in some of my favorite childhood movies, but then I discovered his deeper, more serious roles. What Dreams May Come and Dead Poets Society spoke to the darkest parts of me, the parts that understood grief and suffering far too well. His performances felt like someone had reached into my soul and put words to emotions I didn’t know how to express.

When he passed, I struggled to find the words for how it affected me. I can’t say it was like losing a family member—that would feel insensitive to his real family, especially his daughter. But what I can say is that Robin Williams and his movies were a constant companion through every tragic moment of my life. His entire range—his comedy, his depth, his ability to bring both laughter and catharsis—was something I carried with me. He brought me comfort in ways I don’t think I even realized at the time. To not mention that here would feel remiss. His work was more than just entertainment; it was a source of light in the dark.

As I grew into adulthood, I found myself reaching for the classics again—the ones I had watched in my grandparents’ homes. Roman Holiday and Dirty Rotten Scoundrels still hold a special place in my heart, not just for their old Hollywood charm but for the nostalgia they carry. I discovered Eternal Sunshine of the Spotless Mind and resonated more than I wanted to admit with the idea of erasing the past, of wanting to forget pain so deeply ingrained in me.

Then there are the movies I turn to when I need to cry. P.S. I Love You and August Rush both hold that power over me. But Big Fish will always be at the top of my favorites—not only for its stunning visuals and artistry but because I know what it’s like to have a father who tells big fish stories. This film beautifully captured how I’ve always tried to seek out the magic, even in the darkest moments. It’s something I still do—falling into movies and books, using them as an escape, as a way to find the light when the world feels too heavy.

And then, of course, there are the movies that don’t necessarily fit into any category but still mean something to me. Practical Magic, Equilibrium, Twister, and Top Gun all deserve their honorable mentions, proving that I embrace so many different types of films and of course, how could I forget my “when all else fails movie,” Hitchhikers Guide to the Galaxy.

From documentaries to ‘90s teen comedies, kids’ movies to horror and all the classics of the ’80s, I long for the next great story—one that makes me feel something, whether it’s laughter, nostalgia, heartbreak, or awe.

And I’ve learned that if a movie is “based on a true story,” there’s a 9/10 chance someone dies, so I’ve learned to emotionally prepare myself accordingly.

Because when it comes down to it, the movies we love aren’t just entertainment. They’re a reflection of who we are, what we’ve been through, and what we still hope to find in this world.

Movies as Memory: What Stays With Us

It’s funny, looking back at the movies that shaped me. They are, at their core, stories of adventure and longing, of outsiders finding their place, of magic hidden just beneath the surface of the ordinary. I see films that made me feel seen at different points in my life—whether it was the bookish oddball in Beauty and the Beast, the rebellious dreamer in The Little Mermaid, or the raw grief and resilience in What Dreams May Come.

I see the comfort of childhood rewatches, the laughter of favorite comedies, and the bittersweet ache of films that have stayed with me long after the credits rolled. And, of course, I can’t forget the mischievous little joys—like learning a brand new swear word from Dirty Rotten Scoundrels at a very young age, thanks to my grandpa’s lack of censorship. (A defining moment, truly.)

Movies, like books and music, are more than just entertainment. They’re a reflection of what moves us, what comforts us, and what lingers in our hearts. Maybe that’s why picking just one favorite feels impossible—because our favorite stories grow with us. And as long as there are new movies to discover and old favorites to revisit, I’ll never stop searching for the next one that makes me feel something unforgettable.

So now it’s your turn…what’s–let’s say–3 of your favorite movies?