How 'The Parent Trap' Became The Most Loved Film Of Your Childhood, As Told By The Cast & Crew

by Rachel Simon
Originally Published: 
Kristin Mahler/Bustle

On a summer day in 1998, two 11-year-old girls were sent to sleepaway camp — and the world was never the same. Well, not quite; although The Parent Trap was indeed a success upon its July 29 release, coming in #2 behind Saving Private Ryan, most reviews were pleasant (Breakout star Lindsay Lohan! Those gorgeous houses!), if not glowing (plot holes, much?). Yet, over the last 20 years, Nancy Meyers' comedy about twins separated at birth has become a classic, the movie nostalgic Millennials (and their parents) can't stop watching, quoting, and obsessing over — and now, with the ability to stream the movie, a new generation of viewers is experiencing it for the first time. At this point, it's easy to feel like there's nothing about the film fans don't know, but according to the cast and crew, surprises and The Parent Trap go together like Oreos and peanut butter.

For one, Lohan — who'd go on to become a massive teen star in the years following The Parent Trap — almost wasn't Hallie and Annie at all. "The very first young actress I auditioned was Mischa Barton," casting director Ilene Starger reveals. Yet despite Barton's talent (she'd go on to get her own breakout role in 1999's The Sixth Sense), she wasn't the right fit, nor were the hundreds of other tween girls who auditioned. It wasn't until then-10-year-old Lohan came into the picture that the filmmakers knew they'd found their lead. Recalls Starger, "She was smart, real, fresh, and utterly charming... she was just an ebullient young girl who brought the sun with her."

And she left with a fan following, a lot of fame, and the ability to do the world's most complicated handshake. In honor of The Parent Trap's 20th anniversary, here's an exclusive look at how the beloved movie came to be, complete with insights on prank wars, camping trips, and why we still hate Meredith Blake after all this time.

Finding Hallie And Annie

After writer-director Meyers and writer-producer Charles Shyer decided to remake 1961's The Parent Trap, auditions to find the new protagonist were held.

Ilene Starger (Casting Director): I began casting The Parent Trap out of my New York office in the spring of 1997. We auditioned hundreds of girls from the U.S. and from the U.K., both in person and via submission of videotapes... Nancy, Charles, and all of us knew that finding one young actress to play Hallie and Annie would be a daunting task; it really was challenging, in terms of finding someone appealing and talented, with intelligence, warmth, and charisma who also seemed "real," and not too polished or too cute or experienced in a show business-y kind of way. Lindsay came in fairly early on in the process.

Lisa Ann Walter (Chessy): I heard them talking to Dennis [Quaid] about Lindsay, that they had already found somebody in New York, like, "she’s wonderful and she’s precious and she’s got all these freckles and wait till you meet her."

Starger: She ultimately tested for the role alongside a few other actresses, all of whom read with Dennis Quaid and Natasha Richardson on film. But by that point, Lindsay was the front-runner, and we were all rooting for her.

Filling Out The Cast

Dennis Quaid and Natasha Richardson were chosen early on to play parents Nick Parker and Elizabeth James. Lisa Ann Walter, Simon Kunz, and Elaine Hendrix were picked for the roles of housekeeper Chessy, butler Martin, and Nick's fiancée, Meredith, respectively.

Walter: I didn’t know it was Chessy the first time. It totally sounds like Jessie. And I had to say to the team, "What the hell is a Chessy? I don’t understand Chessy. There’s nobody named Chessy..." It’s not short for anything. It’s named after a decorator that Nancy had.

Simon Kunz (Martin): I actually went in for a one-line role in the film. I think it was a wedding photographer. It was one scene, but I just went in for the meeting because Nancy and Charles were in town. I met them at this hotel in London and I just went in and read my one line... and they both kind of sat back and narrowed their eyes and looked at me and went, "There’s another role that we think you might want to have a look at it? It’s this valet, butler type and maybe we give you the script, you could just go away, come back in an hour and have a look at that?" And I went, "Yeah, sure, of course." So I did that and I went away and found a coffee place and sat down and had a look at it, read it, and thought, "This is a lot better than one line."

Walter: My whole life, I adored Dennis Quaid — like, from The Big Easy. Not just adored, had a stupid, ridiculous crush on. I didn’t know how I was going to get through an audition and not be shaking... [but he was] super charming. Put me at ease.

Elaine Hendrix (Meredith Blake): I got called for a last-minute audition. I was living in West Hollywood and I was asked to drive over to Burbank and so I did. And I read, and the next thing I know I’m being asked to come in on a Saturday to read with Dennis.

Walter: I heard [the filmmakers] talk about Elaine [to Dennis]. They were like, "Wait till you meet this girl." ... And then all of a sudden, Elaine breezes in the room looking like a million bucks all in 20s and Dennis just turns and looks at them and I see him mouth the words, "Are you kidding?" I mean, it was like a scene in a movie. Oh, it was fantastic. I just was dying laughing and I just stood up by then because I had already got done working and went, "Well, I’ll leave you to it." It could’ve been a scene from The Parent Trap.

Starger: Dennis has that dramatic (and comedic) gift. Natasha [Richardson] had that, too. She was my first thought when I read Nancy and Charles’ script. I had met her a few years before then, and had seen her on stage and on film, and she was the embodiment of a kind of golden radiance, class, incredible talent, and yet she also had a great sense of humor about herself and others. For me, there was never another serious contender for the role.

Buena Vista

Going To Camp — And Making Those Iconic Scenes

The film's early sections are set at a summer camp in Maine, where Hallie and Annie — separated at birth, with no knowledge that they're twins — unexpectedly meet. When Annie is dropped off by her family butler, Martin, they perform a multi-step handshake that would go on to be emulated by millions of fans.

Kunz: The first time [Lindsay and I] met up, we worked on the handshake idea, about what it could be. I think I’d done something in the audition, just mucking about without Lindsay there, just doing silly moves. They liked a few of those, and so we basically spent an afternoon, two or three hours really, just working out that routine... If you ask me right now [to do it], I’d know one or two bits there, but I tell you what, it would only take me 20 minutes and then I’d have it absolutely down pat.

While Hallie and Annie later become close, they originally can't stand each other, and so they turn to a camp favorite: a prank war, featuring Camp Walden counselors (played by Polly Holliday and Friends' Maggie Wheeler).

Maggie Wheeler [Marva Jr.]: Oh my god, we had so much fun. We shot the [cabin prank war] scene in two locations, at the camp and on a soundstage... and the hilarious thing about it was the drive in the little golf cart from the set the cabin to the showers. It was an open air golf cart, so with the air blowing on us, the chocolate hardened and so by the time we got to the showers, we were like chocolate bunnies... We had to move our limbs and crack the chocolate off.

Hallie and Annie's prank-throwing bunkmates included future Vampire Diaries star Kat Graham, only a few years younger than Lohan at the time.

Kat Graham (Jackie): I remember Lindsay was really into Sugar Ray and Hanson. She was obsessed with them, and I remember I got into them just so I could have something to talk about with her.

To London And Napa Valley

After Hallie and Annie discover they're twins, they hatch a plan to switch places. Although it works for a while, eventually Chessy — who's known Hallie all her life — realizes in an emotional (and French-laden) scene that the girl she's talking to is actually Annie.

Walter: We did that scene over a couple days and 73 takes, I think... about halfway through all those takes, people were giving me different directions and Charles started to have other ideas and started to ask Nancy to ask me to do different things. I started to question what I was doing and thought, ‘Oh, my god. I’m f*cking this up. Maybe I’m doing the wrong thing and maybe I suck, maybe I’m a terrible actress, maybe I’m just awful." And I was sitting in a chair trying to get back to that beat and do my work and [Dennis] came over and he put his hands down on either side of me. He put his forehead against mine, and he said, "I think the work you’re doing is magnificent." And I burst into tears. It’s just little things like that — it's how many years later, and I’ll never forget how that made me feel.

Buena Vista

Introducing Meredith Blake

When Hallie and Annie conspire to reunite their long-divorced parents, their plan hits a snag when they discover that Nick is engaged to Meredith Blake. A stylish publicist with a love of money and a hatred of kids, Meredith became one of the most iconic movie villains of the '90s — even if viewers today can't get over the fact that she's only 26 (!).

Hendrix: I get so many people who will message me or post like, "Oh, my god, I’m turning Meredith Blake’s age." Somehow I think they’re worried that’s going to turn them into Meredith Blake... I certainly didn’t dress the way she did when I was 26. She was very coiffed. I was wearing ripped up fishnets and jean shorts... I don’t know if people really believed she was 26.

Walter: Just recently, somebody made a post about her and it got like, 750,000 likes and it’s all about sending the kids off to Switzerland, off to boarding camp. Now, girls from the Kardashian generation are like, "Girl, I hated you when I was young. But now I see you were just trying to land the bag. And those kids ruined it." Now, she’s a role model.

Hendrix: There was a while there when I got frustrated that it followed me. But then I made peace with it, and now I’ve so embraced it because it’s just so fun. And especially now, after playing all the different types of characters, being the villain really is the most fun to do.

Going Camping

In one of the movie's most iconic scenes, Nick, Meredith, and the girls go camping — and the twins do everything in their power to make Meredith miserable, including pushing her sleeping bag into the lake.

Hendrix: [In the sleeping bag scene], I lift my leg as I’m sleeping — I pitched that to Nancy. I was like, "I think people, when they’re on sleeping pills, do weird, twitchy things." And that was something that I can’t believe got left in there. But it did... [And] the bird actually was attacking me because the trainer said... [the bird] thinks your nails are strawberries. He sees the red." So the bird kept attacking me, which I didn’t care about. I’m a big animal lover. I thought it was hilarious. And then, oh, god, the water. I got hypothermia.

While on the trip, Meredith also almost swallows a lizard, another result of the girls' shenanigans.

Hendrix: Everybody always asks about the lizard scene. That’s probably going to be on my tombstone. People everywhere I go say, "Was it real? Was it real?" And I like to believe that people don’t really want to know 'cause they want to maintain the movie magic and while we were filming it I was sworn to secrecy... I just tell people, "Listen, it’s movie magic. There’s a real one, a fake one, and a computer one in there. Go back and watch and see what you can figure out."

L Is For The Way You Look At Me...

Although Nick and Elizabeth's rekindled romance is the heart of the movie, Chessy and Martin develop a flirtation of their own, culminating in a proposal and wedding seen during The Parent Trap's end credits.

Walter: Oh, my god, we had so much fun with that. And we didn’t know it until they did the photo shoot. We were like, it’s a party scene, blah blah blah, we’re going to dance, and they were like, "Well, here’s what’s going to happen." And we were like, "Really?!" We had no idea.

Kunz: It’s just charming, isn't it? Lisa Ann was fantastic. We clicked immediately... we’d just sit and watch movies when we had downtime and eat crappy food and do all that kind of stuff that you do, just hanging out together.

Buena Vista

The Movie's Release

On July 29, 1998, The Parent Trap was released in theaters to generally positive reviews. Critics especially praised Lohan's double roles, with many reviewers labeling her a major breakout.

Walter: I've worked with a bunch of kids before they make [their first big movie], like Dakota Fanning in War of the Worlds. And I’ll tell them, "I’m magic. If you work with me, you become a huge star. But have good manners." But [Lindsay] was already a pro.

Wheeler: I was just stricken by her level of talent. She was so good, so present. She was an enchanting young person, and there was a lot of pressure on her. It was a big job.

Walter: There was a lot of responsibility [on her] not just because of the work, which she had plenty of, but I think also because... there was a lot going on with her home stuff. She was carrying a lot on little 11-year-old shoulders... she was [dealing with] an unbelievable amount of crap.

Over the years, Lohan would shoot to superstardom — and The Parent Trap would become a beloved classic.

Hendrix: With any project you do, you hope it does well. But for this to become what it’s become... every single day I get someone on the street, a fan mail or a message on social media. Every single day. No exaggeration. Because it plays all the time and it plays all over the world.

Kunz: I’m delighted that people still tap me on the shoulder and go, "Are you...?" and you can see their little faces light up. Because it’s a great memory for them, and it was a great memory for me.

Walter: When I would go out on the street, kids would say, "Oh, my god. Mom, Mom, that’s the nanny." And then they’d come running up, like, "I love you. Oh, my god, I wish you were my nanny," or, "I wish you were my mom," in front of their own mom! I’d be like, "Keep that on the DL. That’s not cool."

Wheeler: I’m always a little startled when people say, "Oh, you’re from The Parent Trap" because it's true, I get recognized as Janice [from Friends] all the time. But if somebody specifically comes up to me, usually what they do is mimic the hand motion that I made when I sent the kids to the isolation camp. I did some little curly-q with my finger, and that’s what people usually do when they recognize me from The Parent Trap.

Buena Vista

Losing Natasha

In 2009, Natasha Richardson tragically died after a skiing accident, leaving behind husband Liam Neeson and two young sons. Her death was mourned by fans the world over, as well as by her Parent Trap co-stars, many of whom had grown to know her well.

Walter: What I remember most about her is when she talked to her husband one day when I was walking by her trailer... She picks up the phone and it’s Liam. And immediately she turns from this like, "Let me drink my white wine and gossip" [person] into a giddy little girl talking to a man that she is crazy, stupid in love with... She just adored her husband and her kids. So, I mean, yes, of course it’s a loss to the acting world. But, she was just a fabulous woman and a fabulous mom.

Starger: The film, to me, takes on added poignancy now because of Natasha’s untimely death. She was a wonderful person and had so many gifts.

A Lasting Legacy

Many of the movie's stars have maintained close bonds over the years even as they pursue different careers in film, TV, stage, and activism.

Wheeler: I haven’t seen Lindsay in many, many years. I ran into her a couple of times shortly after the movie or in the years right after, but I haven’t seen her in forever. But I certainly see Elaine and Lisa.

Walter: [The movie] gifted me with Elaine as my best friend… literally from day one, when they had us in this hotel in Napa, we spent a four-hour dinner talking and haven’t stopped in, holy sh*t, 20 years.

Hendrix: It was like we were all in our element, and going to work every day was literally going to the happy place.

Wheeler: I feel so honored that I got to be a part of something that’s become such an enduring classic.

Hendrix: I got a fan letter from this young man in Russia who, in the letter, said he grew up in an orphanage. They didn’t have a lot, but they had a few movies... and The Parent Trap was one of the movies that they watched over and over and over. He talked about how much hope and happiness that movie brought him. I get choked up talking about it because for me, that’s why I do this, you know? Entertainment is supposed to help people lift up out of their own lives. It’s supposed to make them think and entertain them and inspire them and do just what [The Parent Trap] did. I could’ve never, ever have predicted that. And I’m just so honored.

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