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The Parent Trap turns 25: See how the cast has changed since, with Lindsay Lohan, Lisa Ann Walter, and more
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The Parent Trap turns 25: See how the cast has changed since, with Lindsay Lohan, Lisa Ann Walter, and more
(THE PARENT TRAP) USA 1998, director: Nancy Meyers, LINDSAY LOHAN, studio: Walt Disney© Alamy

The Parent Trap turns 25: See how the cast has changed since, with Lindsay Lohan, Lisa Ann Walter, and more

The Disney remake turns 25!

Ahad Sanwari
Ahad Sanwari - New York
Senior WriterNew York
July 20, 2023
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It's time for another trip to Camp Walden, because Disney's 1998 remake of The Parent Trap, directed by Nancy Myers, officially turns 25 years old!

The reimagining of the 1961 film of the same name, which in turn is an adaptation of Erich Kästner's 1949 German novel Lisa and Lottie, was a critical and commercial hit when it was released on July 20, 1998.

PARENT TRAP 1998 Buena Vista film with Natasha Richardson at left and Dennis Quaid© Alamy
1998's "The Parent Trap" was released 25 years ago!

However, it has since become a cult classic, often revisited for its heartwarming story, nostalgic pop culture moments, and a stellar debut performance from Lindsay Lohan.

In honor of the movie's milestone anniversary, let's take a look at its cast and how their lives have changed since…

Lindsay Lohan

Lindsay Lohan during "The Parent Trap" Los Angeles Premiere at Mann National Theatre in Westwood, California, United States© Getty Images
Lindsay at the movie's Los Angeles premiere in 1998

Beating out the likes of Scarlett Johansson, Mara Wilson, and Jena Malone for the dual role of twins Hallie Parker and Annie James, Lindsay's big film debut established her as one of the brightest young stars of the late '90s.

MORE: Lindsay Lohan makes shock on-air reveal about The Parent Trap

She continued her association with Disney, starring in hits like Freaky Friday (2003) and Herbie: Fully Loaded (2004), although the peak of her on-screen career came in 2004's Mean Girls, which remains one of the most quotable teen comedies of all time and made her a bonafide star.

Lindsay Lohan and her husband Bader Shammas© Getty Images
The actress has weathered several storms and is now a doting wife and new mom

Personal struggles in the mid-aughts led to stints in rehab and incessant tabloid coverage, the kind that effectively tarnished her teen idol image. However, she's since returned to the public eye as a glowing new mom, having recently welcomed her first child with husband Bader Shammas. And the now 37-year-old made her film comeback last November with Netflix's Falling For Christmas.

Dennis Quaid

Dennis Quaid and Meg Ryan at "The Parent Trap" Los Angeles Premiere© Getty Images
Dennis and then wife Meg Ryan at the movie's Los Angeles premiere in 1998

Already a screen heartthrob by the time The Parent Trap rolled around, Dennis Quaid played Hal Parker, Hallie and Annie's wealthy father who owns a vineyard in Napa, California.

MORE: Dennis Quaid has the best response to his The Parent Trap co-star after engagement joke

The actor, now 69, has since followed that up with critical and commercial success in films like Traffic (2000), The Rookie (2002), The Day After Tomorrow (2004), The Special Relationship (2010), and A Dog's Purpose (2017), receiving the best reviews of his career for his supporting turn in 2002's Far From Heaven.

Dennis Quaid attends the red carpet of the Filming Italy 2023 on June 24, 2023 in Santa Margherita di Pula, Italy© Getty Images
Through several highly publicized relationships, the actor remains one of Hollywood's most bankable

Dennis attended the Disney film's 1998 premiere with then wife Meg Ryan, with whom he welcomed son Jack Henry Quaid, also an actor. They divorced in 2001, and from 2004-2018, he was married to Kimberly Buffington, with whom he welcomed twins. In 2020, he tied the knot with current wife Laura Savoie.

Natasha Richardson

Natasha Richardson during Premiere of "The Parent Trap" at Mann's National Theater in Westwood, California, United States© Getty Images
Natasha at the movie's Los Angeles premiere in 1998

A descendant of the legendary Redgrave acting dynasty, English actress Natasha Richardson was on the rise in 1998, when she played Elizabeth James in The Parent Trap, Annie and Hallie's mother and Nick's ex wife.

RELATED: Natasha Richardson's son Micheál 'still can't comprehend' his mother's death

The same year, she won acclaim and several awards, including a Tony, for her leading turn in the Broadway revival of Cabaret, and followed it up with hits like Maid in Manhattan (2002) and The White Countess (2005).

Natasha Richardson and Liam Neeson during "Seraphim Falls" New York Screening Hosted by The Cinema Society - Inside Arrivals at Tribeca Grand Hotel, Grand Screening Room at 2 Avenue of the Ame in New York City, New York, United States© Getty Images
The actress (pictured with husband Liam Neeson) tragically lost her life following an accident in 2009

However, tragedy struck in 2009, when she died of a head injury at the age of 45 after a skiing accident in Canada, leaving behind her two sons with husband Liam Neeson. 

During a 2020 cast reunion, Natasha's co-stars gushed about her warm energy, with Lindsay saying: "Natasha had such an elegance and grace, and she was so maternal to me," and Dennis adding: "[Natasha was] so giving and so glad to be there, and transmitted that joy of being able to do what we do."

Lisa Ann Walter

Lisa Ann Walter attends the world premiere of "The Parent Trap" on July 20, 1998 at Mann National Theater in Westwood, California© Getty Images
Lisa Ann at the movie's Los Angeles premiere in 1998

With the role of the wise-cracking Parker family housekeeper, Chessy, Lisa Ann Walter had her first big hit on her hands with only her second ever film role after making the transition from TV sitcoms.

She followed that up with several more stints on reality competitions and game shows before breaking into the mainstream once again in 2021 with the ABC mockumentary Abbott Elementary, receiving much acclaim and several awards for her turn as the (once again) wise-cracking Melissa Schemmenti, a Philadelphia school teacher with all kinds of connections.

ALSO READ: Why Abbott Elementary Star Janelle James will never reveal her age

ABBOTT ELEMENTARY - Wrong Delivery After Janine gets a look at the new charter school down the street, she becomes determined to fix up Abbott and make it just as good. As Gregory goes out of his way to avoid Barbara due to an awkward situation with his © Getty Images
The star experienced a career resurgence in 2021 with ABC's "Abbott Elementary"

Lisa Ann, now 59, has managed to keep her personal life away from the spotlight, though. She was married to actor Sam Baum from 1983-1999, welcoming son Jordan in 1988 and daughter Delia in 1992. In 2000, she welcomed twins Spencer and Simon on October 11, the same day that Hallie and Annie were born as well!

Elaine Hendrix

Elaine Hendrix, co-star of the movie, arrives at the Mann's National Theater© Getty Images
Elaine at the movie's Los Angeles premiere in 1998

After turns in the original Get Smart series and another cult classic, Romy and Michelle's High School Reunion (1997), Elaine Hendrix's turn as the antagonistic Meredith Blake turned out to be her big break.

She followed that up with years of cameos and supporting roles in some popular 2000s shows, like NCIS, Joan of Arcadia, and Anger Management, before taking on the role of Alexis Carrington Colby for three seasons of the Dynasty reboot from 2019-2022.

Elaine Hendrix and Lisa Ann Walter attend the SAG-AFTRA Foundation Conversations - Career Retrospective: Lisa Ann Walter at SAG-AFTRA Foundation Screening Room on June 16, 2023 in Los Angeles, California© Getty Images
Despite their on-screen rivalry, the two co-stars have remained close over the years

Elaine has kept her personal life quite guarded, and doesn't seem to have a husband or children. However, she has been quite public about her love for her co-star Lisa Ann Walter, and their close friendship has stood the test of time.

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