8 Perfect Fantasy Movies That Get Better With Every Rewatch

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Published May 17, 2026, 2:40 PM EDT

Michael Block is a 14 time GLAM Award nominated writer, producer, and host of the podcast Block Talk. Throughout his time in the entertainment industry, he has worked on and off Broadway as a stage manager, written several produced plays, critiqued hundreds of theatrical performances, drag and cabaret shows, and has produced events randing from drag competitoons to variety concerts!
On Block Talk, he interviews nightlife personalities, covers the wide world of entertainment through features, ranking episodes, and recaps ALL of Drag Race, as well as Dragula and Survivor. He has interviewed hundreds of RuGirls that span the globe at DragCon NYC, DragCon LA, and DragCon UK.
In his free time, he makes one-of-a-kind jewelry and gift baskets with his mom. He is a proud member of the LGBTQ+ community.

The fantasy genre in cinema remains a timeless escape where we can go for a few hours and forget the world's worries. Some fantasies show us the greatest loves of all, while others take us on extraordinarily epic journeys. No matter where we go or who we go with, fantasy films are far from our reality, and we love them for that.

There are so many beloved and iconic fantasy films, but how many of them truly have that rewatchability factor? Not only does the movie have to be good, but it also has to provide some sort of comfort or solace when we return. We continue to rewatch these films because they also happen to get better with every watch. Maybe it's because you get to experience the story in a new manner or through a different character's perspective, or maybe it's simply because the film resonates at a different stage of life. The films on this list are not just great, but they get better every time.

'Barbie' (2023)

Barbie and Ken, played by actors Margot Robbie and Ryan Gosling, smile happily while driving a speedboat in Barbie.

There isn't a single generation that doesn't have some affinity for Barbie. Maybe it's through playing with the iconic dolls or having a laugh with the Aqua song "Barbie Girl." In a time when reboots and adaptations were a-plenty, it was inevitable that the beloved toy would find her way to the silver screen. In 2023, it happened, and it was glorious. Directed by Greta Gerwig, the existential comedy follows Barbie (Margot Robbie) as she faces a crisis of perfection, forcing her to travel from the idealized "Barbieland" to the real world. Alongside Ken (Ryan Gosling), Barbie must navigate humanity's complexities, confronting challenges in gender dynamics, consumer culture, and the pressures of being a woman.

A film for the whole family, but very much meant for the kids at heart, Barbie became a blockbuster sensation because it was fun, refreshing, and more than a typical popcorn flick. There's a very good chance that, based on box office numbers, you likely saw Barbie on the big screen. With dense, self-aware humor, intricate visual storytelling, and layered themes, repeat viewings allow you to appreciate more subtle details you may have missed on first viewing. Not only is it a fun film with extraordinary performances, but there's also a human journey for the once-plastic toy. Chances are that when you first saw the film, you may not have been entirely familiar with the entire Barbie and Ken ensemble. Now, you probably have, and you get a chance to see them in a new light.

'Beauty and the Beast' (1991)

Belle and the Beast dance in the ballroom in 'Beauty and the Beast.'

There is absolutely no other tale as old as time, quite like the Disney animated classic, Beauty and the Beast. The groundbreaking feature tells the story of a prince turned beast who seeks to transform back into a human by finding the one who can break the spell. When a young provincial girl named Belle (Paige O'Hara) arrives at the castle, the Beast’s (Robby Benson) enchanted servants attempt to make the pair fall in love and reverse the curse. Boasting a stellar soundtrack of iconic songs and visual storytelling that reshaped animation forever, Beauty and the Beast brings a Broadway-style musical to the big screen through a richly emotional tale with a timeless message.

Disney has continued to expand the roster of Disney princesses, yet Belle remains one of the most beloved. Her story as a strong, independent mind resonated at the time and has become even more progressive with time. She was never a damsel-in-distress trope, allowing a genuine, heartfelt connection to arise. Some of us might see ourselves in the beast; the story from his eyes gives us hope that true love can break our personal curses. Beauty and the Beast remains an enchanting visual experience with its pristine, forward-moving animation style and sensational production numbers. There's not a flop on that soundtrack!

'Mary Poppins' (1964)

Mary Poppins and Bert in white and red outfits dance in an animated world in Mary Poppins

A great family fantasy film must have an inherent sense of nostalgia so that whenever you watch it, you're filled with the same joy you felt when you first laid eyes on it; that's exactly how it feels watching Mary Poppins. Mary Poppins is the story of a magical, "practically perfect" nanny named Mary (Julie Andrews) who arrives by wind to care for the neglected Banks children, Jane and Michael (Karen Dotrice and Matthew Garber), in early 20th-century London. Seamlessly blending live-action with animation through a toe-tapping score that literally had us stepping in time, Mary Poppins is a thematically rich movie that resonates with its sense of wonder.

As a child, chances are you were taken by the brightly filmed sequences where humans danced alongside penguins and rode a carousel that took flight. As an adult, the magic is still present, but there comes a deeper appreciation for the more mature themes. It's a human story about overcoming grief, nurturing relationships, and fixing a broken family dynamic. You might have had to go through all of your schooling as well to understand just exactly what a suffragette was. In the world of cinema, we've seen the evolution of technical advancements, but watching Mary Poppins today, you're left with a great appreciation for what director Robert Stevenson accomplished in 1964.

'Monty Python and the Holy Grail' (1975)

A group of knights in Monty Python and the Holy Grail

Let's get it out of the way now: they simply do not make comedies like Monty Python and the Holy Grail today, and when you watch the genuine camp classic, you're destined to laugh at the same jokes time after time. Told through interwoven vignettes, Monty Python and the Holy Grail parodies the Knights of the Round Table and their quest to find the Holy Grail. With recurring gags, witty banter, observational humor, and a love for low-hanging fruit, Monty Python delivers with laugh-out-loud comedy. From taunting French knights, a killer rabbit, a witch, and the Knights Who Say Ne, among other famous characters, there’s not a moment that goes by that isn’t hilarious.

Widely considered one of the greatest comedies of all time, Monty Python and the Holy Grail relies on dry wit, observational humor, and intellectual stimulation. Packed with jokes from start to finish, chances are you missed something the first go around because you couldn't stop laughing. With wordplay, puns, absurdity, and slapstick, Monty Python and the Holy Grail also happens to be historical satire at its finest. By being self-aware, the more attuned you become to the humor, the greater your appreciation of the writing and the performances by the brilliant ensemble of Graham Chapman, John Cleese, Terry Gilliam, Eric Idle, Terry Jones, and Michael Palin.

'Pirates of the Caribbean: The Curse of the Black Pearl' (2003)

Johnny Depp as Jack Sparrow in Pirates of the Caribbean The Curse of the Black Pearl looking pensive.

Easily one of the most daring risks Disney ever took was deciding to make a big-budget blockbuster based on a theme park attraction, but what resulted was perfection. Directed by Gore Verbinski, Pirates of the Caribbean: The Curse of the Black Pearl tells the story of eccentric pirate Jack Sparrow (Johnny Depp) and blacksmith Will Turner (Orlando Bloom). The unlikely duo team up to rescue Elizabeth Swann (Keira Knightley) from cursed, undead pirates led by Captain Barbossa (Geoffrey Rush).

An iconic film that perfectly blends adventure, comedy, fantasy, and romance, Pirates of the Caribbean: The Curse of the Black Pearl is everything you want from a rousing action film based on a ride. Visually, it's a striking film: the atmosphere is contagious, the living skeletons are iconic, the costumes and set design are impressive, and the score from Klaus Badelt and Hans Zimmer captured the adventurous spirit. But, perhaps the primary reason the film continues to get better is the nuanced performance from Depp. The film kicked off an iconic franchise, but it's one you can't stop watching time and again.

'The Lord of the Rings' Trilogy (2001-2003)

This one might be cheating, but nowadays, we tend to watch The Lord of the Rings as a full trilogy, so we’re going to make this entry a unified one as we celebrate the Peter Jackson phenomenon. Divided into three masterful blockbuster films, the trilogy is an epic adventure based on J.R.R. Tolkien's beloved novels. To save Middle-earth from Sauron, Frodo Baggins (Elijah Wood), aided by a "Fellowship" of friends and allies, travels to the dark land of Mordor. The journey splits the company, with Frodo and his companion Samwise Gamgee (Sean Astin) guided by the creature Gollum (Andy Serkis), while the others rally the free peoples in massive wars.

The Lord of the Rings centers on friendship, loyalty, sacrifice, and the power of how the smallest individuals can change the course of history. You likely come for the story, but you stay for the impeccable craftsmanship. Filmed in succession, Jackson's remarkable vision became the blueprint that all epics needed to follow. Just getting a glimpse of the lush world that Jackson brought to the screen is remarkably transcendent. Very few fantasy worlds are as immersive on the screen as Middle-earth. Of course, many return to The Lord of the Rings for the extended editions. It's almost as if you get a chance to experience the extraordinary journey for the first time again. A major factor in the high rewatchability is the chance to see the story through a particular character's eyes, and let's face it, there are plenty to choose from!

'The Wizard of Oz' (1939)

Judy Garland as Dorothy being pointed at by Margaret Hamilton as the Wicked Witch of the West in The Wizard of Oz

There is no better classic fantasy film to watch over and over again than The Wizard of Oz. Perhaps a major factor is the joy that comes from passing it down from generation to generation. Filmed in brilliant Technicolor, the masterpiece tells the story of Dorothy Gale (Judy Garland), a young farm girl from Kansas, who is swept away via a tornado to the magical Land of Oz, where she embarks on a quest along the Yellow Brick Road to find the powerful Wizard in the Emerald City to help her get home.

At its core, The Wizard of Oz is a story about understanding that the thing you sought was inside you the entire time. It operates on so many levels, allowing it to get better every time. For children, it's a whimsical fantasy tale; for film buffs, it's a technical wonder; and for adults, it's all about those profound psychological and symbolic themes. Oh, and now, having the perspective through the lens of Wicked adds another sensational new layer. With so much lore behind the film, every watch grants you the opportunity to spot the nuances and intricacies you might have only heard about. As one grows, The Wizard of Oz takes on different meanings.

'Willy Wonka and the Chocolate Factory' (1971)

The ensemble cast of 'Willy Wonka & the Chocolate Factory' stands together and Wonka motions with his cane.

The moment we took a trip to a world of pure imagination, our lives were forever changed. Inspired by the Roald Dahl children's book, Willy Wonka and the Chocolate Factory tells the story of titular candy maker Willy Wonka (Gene Wilder), who invites five Golden Ticket-winning children to his secretive chocolate factory for a magical tour where he tests their morality, revealing that the true prize isn't just candy but finding a worthy heir to inherit his wondrous empire.

Teaching lessons of greed, humility, and good behavior through the humorous misfortunes of the other children, Willy Wonka and the Chocolate Factory has been stuck with us since we first set eyes on the glorious wonderscape. With every watchback, the colorful world grows darker and darker. There is an inherent nostalgia built into it, as we find ourselves transported to a magical world filled with sensational songs, eccentric personalities, and masterful performances from Wilder. But then, as we discover the subtle, dark undertones that were hiding in plain sight, the film operates on a much different terrain. No offense to Johnny Depp and Timothée Chalamet, but our appreciation for Wilder's original take grows with each new adaptation. And just like Wilder's performance, the original adaptation remains its strongest.