1. The Prince of Egypt
1998 • Steve Hickner, Brenda Chapman, Simon Wells • Val Kilmer, Ralph Fiennes
The Prince of Egypt has just about everything that I look for in a movie, not to mention that it’s been in the Smith family movie rotation for essentially my entire life, be it DVD or streaming. With superb animation (and some show-stopping visuals of insane scale), a great story with complex, fully developed lead characters, committed vocal performances from actors and singers alike, and one of the best soundtrack-score combinations in film history, I can’t imagine how I convinced myself for so long that The Prince of Egypt wasn’t my favorite movie. I’m now living my truth!
“I won’t rehash many of my praises since they are very well-documented, but I appreciate this movie more every time I watch it. I’m a sucker for musicals, and when they’re this powerful and respectful of their audiences as these are, they stick with me for a long time.”
2. La La Land
2016 • Damien Chazelle • Ryan Gosling, Emma Stone
I remember going to see La La Land in the theater back in 2016. I was convinced that “Another Day of Sun” was some well-choreographed and composed Coca-Cola ad or something, but when that title card hit, my brain chemistry was forever altered. This film is (at least partly) responsible for my love of movie musicals, Ryan Gosling, and Damien Chazelle and Justin Hurwitz. I feel only a little bad that, in the most recent shaking-up of my rankings, La La Land stayed in second place after Inside Out was ousted by The Prince of Egypt.
“[La La Land]’s got the perfect mix of engaging, dynamic storytelling and lovable, complicated characters, and Gosling and Stone were the perfect choices for Mia and Sebastian. I think I’m equally in love with the both of them in this movie, just as much as they’re in love with each other. I’ve said that my favorite movies will always exude magic above all, and that’s exactly what La La Land does for me. Every. Single. Time.”
3. The Lion King
1994 • Roger Allers, Rob Minkoff • Matthew Broderick, James Earl Jones
The Lion King may be the best example of a movie that I loved as a kid, yet as I get older, I get more and more out of with each rewatch. It’s always been a stunning movie and certainly a childhood favorite for the music and humor, but my more recent viewings really unlocked the magic of this film, from Simba’s story of identity and redemption to some insanely spiritual vibes and visuals (I will semi-confidently say here that the “Remember Who You Are” sequence is my favorite in any movie, ever). I still love the music and humor, of course, but now that I feel like I’m actually getting the full picture when I watch this film, there’s so much more to appreciate.
“The pure love and passion poured into this film is enough to make a grown man cry (or, in my case, get very near it) every time. The animation was amazing, the score was amazing, the story was amazing, the voice acting was amazing, the comedy was amazing, and The Lion King steadfastly remains one of my favorite (and objectively one of the best) films of all time.”
4. The Princess Bride
1987 • Rob Reiner • Robin Wright, Cary Elwes
As you probably inferred, The Princess Bride held the top spot as my favorite movie for a long time before Inside Out. This was before I had Letterboxd, so the list just lived inside my head, but this movie reigned supreme for at least five years before Inside Out took its place. For the longest time, The Princess Bride was the most magical film I had ever seen, and now having read the book, my appreciation for it has only deepened. I love the over-the-top love, the iconic band of characters, the self-aware humor, and Robin Wright is the second-most stunning woman I’ve ever seen—next to my wife, of course. After a few years of letting this movie slip through the ranks, I’m glad it’s returned to the top 5, and who knows? Inside Out‘s spot at #4 may not be safe*.
“The romance between Buttercup and Westley is iconic—their love feels so organic and the way they speak to and about each other just makes you smile. I can’t confirm this, but Buttercup was probably one of Young Nate’s first crushes, too, but what a good one to have. I don’t think I’ll ever get tired of The Princess Bride; it’s endlessly charming, every character is so easy to root for, and its subtle humor and quotability keep me referencing it even when it’s been years since viewings.”
*Well, would you look at that. It’s July 30, 2026, I’ve reordered my Top 25, and The Princess Bride did pass Inside Out! I’m clairvoyant!
5. Inside Out
2015 • Pete Docter • Amy Poehler, Phyllis Smith
I think it was around the end of high school when I unofficially dethroned The Princess Bride as my favorite movie with Inside Out. Even though that time has now come to an end, this film still has a special place in my heart. This is another one I remember seeing in the theater, too (right after my crush of three years had moved to another state. Middle school drama, I know—riveting); I was both in awe and crushed. Inside Out is Pixar at its finest; layered and accessible for all ages, very funny and musically rich, and there’s always more to find. There may be other Pixar movies that I’ve loved for longer, but none as much as Inside Out.
“As is usually the case with Pixar, the layered story of Joy, Sadness, and Riley hit exceptionally hard, and I think its impact on me grows as I get older—teaching hundreds of Rileys this year and as I’m getting closer and closer to becoming a parent. Such a deep dive into the emotional makeup of a kid, as someone who loves children, is an obvious hit for me, and the music puts it over the top.”
6. Toy Story 2
1998 • John Lasseter • Tom Hanks, Tim Allen
I’ve long loved the Toy Story franchise, and one of the many hills that I’m willing to die on as it pertains to this franchise is that Toy Story 2 is the best of the bunch. There isn’t a sequel, animated or otherwise, that exceeds its predecessor as completely as Toy Story 2 does, and it should be the blueprint for every sequel going forward. There isn’t a scene in this movie that isn’t iconic, a character that isn’t meaningfully explored, and a joke that isn’t gut-bustingly funny. No wonder I have more and fonder memories of Toy Story 2 from my childhood than I do the rest of the franchise; they’re all amazing, but this one hits different.
“From start to finish, this movie is perfect. The story is creative and entertaining, the cast is still amazing, and it’s so funny, too! “When She Loved Me” is one of the best songs in a Pixar movie (or maybe just a movie, period). I’ve seen this movie countless times, but I was still on pins and needles during the last 20 minutes of the movie. I also totally forgot about the post-movie bloopers, which are all hilarious, and I appreciate the effort that the animators put in to create bloopers for their animated movie. Perfect.”
7. Wicked
2024 • Jon M. Chu • Cynthia Erivo, Ariana Grande
When I think about the music that shown to my siblings and I during our impressionable years, I think of country-era Taylor Swift, The Dixie Chicks, The Indigo Girls, and Wicked. I didn’t know anything about the story until we saw the show on stage in middle school, but I knew the music by heart long before that. When this movie came out in 2024, I knew I was going to be obsessed with it, but not to the level that I became. Wicked is the only movie that I’ve seen three times in theaters, which is remarkable and totally understandable. This is a film that is best on the biggest screen you can find, and with as many people as possible. Also, Glinda is my spirit animal.
“There are few musicals—few films, even—that maximize every minute of their runtime the way that Wicked does. Every song was amazing, the performances were all great (though I will be forever in love with Ariana Grande’s Glinda), and the scale, power, and emotion of countless sequences was incredible.”
8. Interstellar
2014 • Christopher Nolan • Matthew McConaughey, Anne Hathaway
It should be pretty clear that the films that usually stick with me the longest—and the ones that earn a spot on this list—would be described first and foremost as magical. Interstellar is the first film on this list whose primary strength isn’t magic. Rather, its technical craft, overwhelming scale, and existential emotional resonance elevate it to the upper echelon of films for me. I remember seeing Interstellar when I was in seventh grade and understanding none of it, but the visuals and spectacle were never lost on me. My most recent rewatch was eye-opening, though, mostly because I understood what was happening! It’ll be hard for Interstellar to lose its spot in the top 10, chiefly because there’s nothing else quite like it here.
“The science of this world and its time travel and inter-dimensionality was surprisingly easy to follow as an adult, while also being super interesting and leading to tons of awe-inspiring and very emotional moments. From virtually all perspectives, Interstellar is a breathtaking modern masterpiece. It’s hard to find a flaw in this film, even in its 2.5+ hour runtime that flies by and doesn’t seem to feature any superfluous scenes.”
9. Project Hail Mary
2026 • Phil Lord, Christopher Miller • Ryan Gosling, Sandra Hüller
I take my top 25 films very seriously, and rarely do I let newcomers enter the fold without extreme vetting (or at least a rewatch). Project Hail Mary became an exception in a couple of ways: not only did it enter the top 25, but it jumped into the top 10. This was one of my most anticipated movies ever: I read the book (and loved it) and the cast and crew seemed hand-picked just for me. Seeing this in IMAX was magical, and given all of the factors, this was an easy entrant into the top 25.
“I had been anticipating this movie for [so] long, so it had a ton to live up to, and I’m happy to say that, not only was this one of the best book-to-film adaptations I’ve ever seen, but Project Hail Mary is in the conversation for one of the best movies I’ve ever seen, period. I was seriously weighing if it was better than Interstellar on the way home. I know I’m probably in the minority there, but I just fell in love with this movie.”
10. The Sound of Music
1965 • Robert Wise • Julie Andrews, Christopher Plummer
The Sound of Music may be the best example of a movie that makes you say, “They just don’t make them like this anymore”. I know I said countless times when I rewatched this for the first time in more than a decade. Even with staggeringly beautiful cinematography thanks to shooting on location in Austria and one of the best batches of songs in any musical ever (for real—watch this again and tell me there aren’t at least 10 absolute bangers)—what stood out most about The Sound of Music was the earnest, emotional story and the incredibly sincere family relationships. The scene where the Captain sings “The Sound of Music” with his kids might be one of the most heartwarming scenes ever put to film. The Sound of Music is magical, plain and simple.
“The Sound of Music left me in awe at every turn, and it truly is a darn shame they don’t make movie musicals like this today. Maybe it’s the transatlantic nature of it all; maybe it’s a batch of adorable child actors doing literally everything well; maybe it’s the bulletproof narrative and soundtrack from Rodgers & Hammerstein. Whatever it may be, The Sound of Music is a classic and a gift, and if my kids aren’t as sweet and musical as the Von Trapps, I don’t want them.”
