Iconic is a word that sometimes gets thrown around a little too lightly, but for millennials, it really is the only word that can be used to describe The Parent Trap. The 1998 Disney film, a remake of the 1964 Haley Mills-led classic, is directed by the queen of the romcom herself, Nancy Meyers. Starring a very young and very freckled Lindsay Lohan, the film follows two twins separated at birth, Annie and Hallie Parker, who meet at summer camp and come up with a plot to switch places in an attempt to get their parents, Nick (Dennis Quaid) and Elizabeth (Natasha Richardson), back together. And it was released 25 years ago today – just in case you needed another reminder about the fleeting nature of time.

For 90s babies, The Parent Trap has become a crucial piece of millennial lore. After all, we grew up watching it – probably on a worn-out VHS tape. We quoted along to Annie’s epic burn – “I have clahss and you don’t” – or repeatedly rewound the tape to learn the moves to the twins’ secret handshake. We dreamed of summer camps where we could prank our enemies’ cabins and join in midnight poker tournaments. We cut our own hair into Hallie’s iconic look – that is, one limp chunk at the front chopped off bluntly at the cheekbone. We began slathering our Oreos in peanut butter.  

Over the past 25 years, we – the original Parent Trap audience – have matured. And so too have our perceptions of the film. Meredith Blake (Elaine Hendrix), for instance, has been reclaimed by viewers, and the once-villainous stepmother has been declared a practical icon of girlbossery. “Justice for Meredith Blake,” reads one i-D piece from 2021.

How, then, did this Disney remake become the stuff of millennial legend? 

For one thing, the characters themselves have an enduring appeal. The two mini Lohans became an entire generation’s idol when the film was first released. Now, there are three other adult characters that viewers look to for inspiration. I’ve already touched on the reclamation of Meredith Blake, the film’s young and beautiful villainess. After all, as she oh-so brilliantly tells Annie: “Being young and beautiful isn’t a crime, you know.” With her immaculately coiffed blonde bob, a wardrobe filled with glamorous wide-brimmed hats and linen skirt suits that scream quiet luxury, she is an anti-hero for the ages. It’s no wonder we’ve changed our minds about her.

And then there’s Elizabeth James, the girls’ utterly divine mother. A cut-glass accent, maternal warmth and another quietly luxurious wardrobe come together to make her the ultimate Nancy Meyers dream woman. But in adulthood, we adore Elizabeth James for her all-too-relatable meltdown prior to seeing her ex after a decade – the curlers, sunglasses and slim cigarette are simply too perfect. 

And then, of course, there is Chessy (Lisa Ann Walter), the chilli-cooking, straight-talking housekeeper who knows Hallie better than her own father and doesn’t pull any punches in her exposition of Meredith and Nick’s budding relationship. 

In hindsight, The Parent Trap is a treasure trove of female icons. 

The script also stands the test of time. Admittedly, there are some logical flaws built into the film’s premise. As an adult, it’s hard to stomach the idea that these parents agreed to simply take one twin each and forget about the other one. The astronomical success of the girls’ parents is also a stretch. Nick built a multi-million dollar winery and Elizabeth became a world-famous wedding dress designer. Really?

Nevertheless, the script, co-written by Meyers and her then-husband Charles Shyer of Father Of The Bride fame, is kind of incredible. The film is filled with charming, quotable lines that capture that exact kind of optimism and zest for life that came with being an 11-year-old in the 90s. There are also clever nods to the original 60s film and an exemplary soundtrack filled with banger after banger.

But what really makes The Parent Trap an all-time classic is its maturity. Although we fell in love with it as children, it’s not merely a light-hearted kids’ movie – it’s a surprisingly mature romantic comedy that hinges on the emotional complexity of rekindling an old romance. In fact, the moment when Nick shows Elizabeth the bottle of wine he saved from their wedding rivals any of cinema’s more famous romcom scenes.

After a quarter of a century, The Parent Trap is just as satisfying to watch as ever; in fact, much like Nick’s treasured, dusty wine bottles, it may even get better with age. With its unique mix of 90s nostalgic appeal and nuanced, complex romance, it’s sure to retain its place in millennial history for years to come.

Images: Disney