Rodgers and Hammerstein’s Cinderella (1997)

What a timeless duo

We’ve said it once and we’ll say it forever: Rodgers and Hammerstein’s 1997 Cinderella was lightyears ahead of its time, and still holds water.

So much of the film was revolutionary. Brandy’s role as Cinderella was a big moment for Black girls everywhere and for Black culture, and the supporting cast of Whoopi Goldberg, Bernadette Peters, Paolo Montalban, and not to mention Whitney Houston is still the only good example of colorblind casting.

After months of pleading from fans, the film recently made its way onto Disney+ and is delighting a whole new generation just as much as the old ones. You never grow out of the feeling of effervescent joy and almost juvenile hope you get from hearing Whitney Houston sing that “impossible things are happening every day,” and now more than ever that’s something we all need to hear.

The Mighty Ducks (1992)

Like so many classic Disney films, The Mighty Ducks got a remake. The new version, The Mighty Ducks: Game Changers, shows a present day version of the titular team which is no longer a home for misfits and underdogs but an exclusive, competitive powerhouse — we all become the things we hate, I guess. Naturally, the new series follows a new team made of underdogs to reinvent the classic sequence of the original in a new context.

Whether you’re catching up to gear up for the reboot or disavowing the new version completely, the 1992 film is the kind of movie you can watch on repeat. Starring a young Joshua Jackson as Charlie and Emilio Estevez at his peak, you can’t go wrong with the feel-good coming of age story — or even with the sequels, which are also all available to stream.

The Princess Bride (1987)

Over the 30 years since its release, The Princess Bride has endured. Each rewatch is a reminder of how much of its language and how many of its jokes are embedded so deeply into our cultural lexicon. The casting also feels like a minefield of memory, remembering what younger versions of household names looked like when they were only sort-of famous.

What makes The Princess Bride a classic is that it is, at its heart, a classic story. But its self-awareness makes it more than just a fairytale or even just a slapstick adventure story. It’s a little bit of everything for everyone. (Thank God Quibi failed before it could manifest its Joe Jonas and Sophie Turner remake.)

Sky High (2005)

Peep Cousin Greg in the back

Sky High somehow only gets better with age. For example, we couldn’t appreciate then that the angsty Warren’s name was literally a play on War and Peace. And who could have predicted that the then awkward and nerdy Nicholas Braun would now be known as the still awkward but even more beloved Succession character Cousin Greg?

Disney may have all the Marvel films on deck, but Sky High doesn’t take itself so seriously. It’s like a goofier version of X-Men, less concerned with the grit and the angst and more so with the characters’ coming of age.

Cool Runnings (1993)

The ultimate feel-good film, Cool Runnings tells the story of the first Jamaican bobsled team. Based on a true story, the film follows a team of Jamaican sprinters who miss out on qualifying for the Olympics as runners so instead take on the winter Olympics as bobsledders.

Sister Act (1992)

Whoopi in the ’90s didn’t miss. When the GameStock thing happened, I rewatched The Associate (despite its unfortunate Donald Trump cameo) to pretend to understand Wall Street and, like, stocks. And to me, her Oscar-winning role in Ghost eclipses even the scene where Patrick Swayze and Demi Moore make the pottery or whatever.

Remember the Titans (2000)

Sorry Sandra Bullock in the Blind Side, Remember the Titans was the sports movie that fixed racism — or at least made the most enduring attempt. The post-racial fantasy, ubiquitous in the late 90s and early 2000s, imagines that good will and football are enough to change the world, and I almost believe them.

Home Alone (1990)

Home Alone plays seemingly on repeat on every cable network every Christmas, but in the off season it’s nowhere to be found. Now that the series is on Disney+, there’s no need to wait until December to watch it. There’s no wrong time to watch Macaulay Culkin run around his house setting booby traps and laughing in delight.

Toy Story (1995)

Let’s forget for a moment that the Hanks currently in the spotlight is Chet Hanks for his White Boy Summer and return to simpler times: when Tom Hanks immortalized the character of Woody in Toy Story.

The saga lasted four movies and fourteen years, culminating in the 2019 Toy Story 4 which had audiences of children and grown ups alike in tears, but the first is still the best to recapture that childhood feeling instantly.