What makes movies rewatchable? And a list of the 50 most rewatchable movies ever

With the Advent of Netlix and Hulu and Amazon Prime, I don’t feel like I need to own movies anymore. Well, kinda. None of those services have everything and there are some movies that I feel a unique connection to that I want to be able to watch them at a moment’s notice.

Some movies are incredible and yet I have no interest in watching them more than once or twice. Schindler’s List falls into this category. I found it so deeply moving that I don’t ever want to see it again. It was so painfully memorable that I don’t need to.

And then there are movies that aren’t so great, but I come back to them again and again. They’ve become friends. Not the most edifying of friends, but friends none the less.

So, what is it that makes a movie rewatchable?

It’s not the plot. The plot is what pulls me in the first time and even the second time. But once I’ve got the plot, it doesn’t pull me back again.

It’s the characters. This is why there are A-list actors and actresses we keep going back to again and again. They’ve become friends. In some cases, we have deeper feelings for them than we do for members of our own extended families.

It’s the relationships. This is an extension of the previous point. But in this case, it’s not the relationship we have with the characters, it’s the relationships between the characters themselves that draws us. Bill and Ted. Frodo and Sam. Westley and Buttercup. The Avengers. Watching their relationships gives us a feel for what’s right and wrong in our own relationships and a window into what we’d like our relationships to be like. This is true both of romantic relationships, friendships, and family relationships — all three of which we all struggle at.

It’s the way they make us feel. Some movies play the sentimental card. Other movies play the adrenaline card. A few rare ones hit on both. But they’ve got to touch our emotions in a way that we want them to be touched again whether they are on the sad or the happy ends of the spectrum.

OK. So, here’s my list. I’m dividing it into several genres. But one movie stands outside of them and above them: The Princess Bride. To me, it is the perfect movie. It has everything and defies bring reduced to a single genre. Enough said.

Christmas/holiday movies

Elf (2003). The ever-absurd Will Ferrell is at his most relatable and quotable in yet another we-gotta-save-Christmas movie, making it rise above the rest.

How the Grinch Stole Christmas (1966) & A Charlie Brown Christmas (1965) — These made-for-TV specials clock in at 26 and 25 minutes respectively which should drop them out of the movie category. But hey, I’m making this list, so I get to bend the rules. They’re here because they’re well-paced, well-told classics that capture the Christmas spirit in ways that Rudolf and Frosty and others simply don’t.

A Miracle on 34th Street (1947) — A sentimental classic that doesn’t get boring like (and I’m going to offend people here) It’s a Wonderful Life (1946).

National Lampoon’s Christmas Vacation (1989) — Hilarious. Quotable. John Hughes-penned. Chevy Chase in one of his best awkward roles.

Honorable mentions: A Christmas Story (1983), A Child’s Christmas in Wales (1987)

Action/adventure movies

Star Wars (1978-continuing, especially episodes IV and V, but not including episode I) — An epic tale that captured me as a 5th grade kid when it began in 1977 and continued to capture successive generations, including my own kids.

The Lord of the Rings (2001-2003) — This trilogy is another epic tale but of even greater proportions than Star Wars. Incredible casting captured the relationships between a large number of characters, but especially the four hobbits. I do not include any of The Hobbit movies as rewatchable, though the so-called Tolkien fan edit comes close.

Pirates of the Caribbean: The Curse of the Black Pearl (2003) — A brilliant initial movie led to three forgettable sequels, which we somehow watch anyway because we love the characters so much and especially Johnny Depp’s Jack Sparrow. “Savvy?”

Mission: Impossible (1996-continuing) — Tom Cruise is the consummate action hero. His cocky smile and self-assured manner is actually believable. Our favorite in the series is the Brad Bird-directed Ghost Protocol.

The Terminator (1984) — The first two movies in this now tired franchise hit hard and with surprising pathos, especially Terminator 2: Judgment Day (1991), making them relevant and rewatchable. Plus, you’ve got the biblical echoes of a man from the future coming to save us and our future through an act of voluntary self-sacrifice.

The Matrix (1999) — I refuse to acknowledge the two sequels, but the initial movie doesn’t get old. As each of my kids gets old enough to watch it, I’ve loved introducing it to them and watching their minds get blown after Neo takes the red pill.

Braveheart (1995) — Mel Gibson uniting the clans and yelling out, “Freedom!” gets me every time.

Honorable mentions: Die Hard (1988). Highlander (1986). A handful of the recent glut of superhero movies — Iron Man (2008-continuing), The Avengers (2012), Spider-Man 2 (2004), Batman Begins (2005) — are some of our favorite family rewatches.

Romantic comedies

Pride and Prejudice (1995 & 2005) — I include both the BBC series and the feature movie here. Yes, I know it doesn’t really fall into the RomCom category, and yet the story does it better than almost anything else.

Sense and Sensibility (1995) — Ditto. Jane Austen rocks! And so does this cast.

17 Again (2009) — I did say that it doesn’t have to be a good movie to be rewatchable, didn’t I? Even better than the main plot of this time traveling hero’s journey is the subplot of the best friend and the high school principal courtship.

The Proposal (2009) — Romantic comedies live and die by the push-and-pull tension in the chemistry between the erstwhile lovers, and Sandra Bullock and Ryan Reynolds are remarkably convincing.

Comedies

Bill & Ted’s Excellent Adventure (1989) — Goofy. Stupid. Straight up funny. Eminently quotable. “Strange thing are afoot and the Circle K, dude.” “All we are is dust in the wind, dude. Dust. Wind. Dude.” “Excellent!”

Get Smart (2008) — Steve Carrell and Anne Hathaway have great comedic and romantic chemistry, with her playing the straight woman to his bumbling genius.

Monty Python and the Holy Grail (1975) — Yet another reminder that plot is inconsequential to rewatching, this movie is all about its absurd sketches and one-liners.

Napoleon Dynamite (2004) — OK, did I say plot isn’t import? This strung-together series of awkward scenes makes being human so much more bearable. Many hate this movie, but my deep-seated affection is unshakable.

Planes, Trains and Automobiles (1987) — The John Hughes directed tension between Steve Martin and John Candy is hilarious until it breaks apart and then becomes tender. “Those aren’t pillows!”

Dramas

The Apostle (1997) — Robert Duvall is legendary as an actor and he plays the saint and the sinner so flawlessly you can’t see the seams between the two.

Gattica (1997) — A sci-fi whodunnit that digs into the heart of what it means to be human.

Shawshank Redemption (1994) — More than just a prison-break movie, chock full of great actors putting in memorable performances.

Lars and the Real Girl (2007) — A film about a loner and his sex doll shouldn’t be as humorous and profound as this working out of emotional brokenness within an accepting community turns out to be.

Family films — musicals & animated

The Sound of Music (1965) — It’s tough to please an entire family. But this has it all. Songs that cross age boundaries. Characters of every age to connect with. And every kind of important relationship is included — faith, first love, adult love, friendship, family, nation — making it a relational home run.

Cars (2006), Up (2009), Toy Story trilogy (1995-2010) — I might as well put every Pixar movie on the list (except for the abysmal Cars 2 which I had conveniently expunged from my memory until just now).

I could easily add a long list of other animated and musical movies — The Little Mermaid (1989), The Music Man (1962), and so on — but this list is already getting way too long. And, yes, I’ve left off a lot of amazing movies and classics. But frankly, as much as I’ve enjoyed them and been challenged by them, so many of them remain in the one- or two-watch category for me. They don’t call to me to be rewatched.

If you haven’t seen any of those on the list above, well, it’s time to pop some corn, settle in the for the evening, and let the screen suck you into worlds that can and should be entered into time and time again.

[And feel free to add any other movies you believe are rewatchable in the comments.]

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