"The Parent Trap" Is Officially 25 Years Old — Here Are 13 Side-By-Sides Of The Cast Then Vs. Now

It's officially been 25 years (!!!!) since The Parent Trap hit theaters, and it's truly still one of my favorite movies ever. Directed by Nancy Meyers, the film gifted us with Lindsay Lohan's movie debut, a classic handshake, tie-dye girl, and so much more.

Lindsay Lohan in "The Parent Trap"
Walt Disney Pictures

So, to celebrate the 25th anniversary of The Parent Trap, here's the cast in their first big movie and TV roles vs. in the movie vs. now:

1.Lindsay Lohan's first role on Late Night with David Letterman in 1992:

Closeup of Lindsay Lohan

Lindsay Lohan as Hallie Parker and Annie James in The Parent Trap in 1998:

Screenshots from "The Parent Trap"

The Parent Trap marked Lindsay's first film role. She then went on to star in countless iconic movies in the 2000s like Life-Size, Freaky Friday, Confessions of a Teenage Drama Queen, Mean Girls, and more.

Walt Disney Pictures

Lindsay Lohan now:

2.Dennis Quaid's first major role in Breaking Away in 1979:

Closeup of young Dennis Quaid

Dennis Quaid as Nick Parker in The Parent Trap in 1998:

Closeup of Dennis Quaid
Walt Disney Pictures

Dennis Quaid now:

Closeup of Dennis Quaid

3.Lisa Ann Walter's first role in My Wildest Dreams in 1995:

Closeup of Lisa Ann Walter

Lisa Ann Walter as Chessy in The Parent Trap in 1998:

Lisa Ann Walter in "The Parent Trap"

The Parent Trap was Lisa's second ever movie role.

Walt Disney Pictures

Lisa Ann Walter now:

Closeup of Lisa Ann Walter

Currently, Lisa stars as Melissa Schemmenti on Abbott Elementary, a role that has earned her critical acclaim.

Frazer Harrison / Getty Images

4.Elaine Hendrix's first big role in Get Smart in 1995:

The cast of "Get Smart"

Elaine Hendrix as Meredith Blake in The Parent Trap in 1998:

Closeup of Elaine Hendrix
Walt Disney Pictures

Elaine Hendrix now:

Closeup of Elaine Hendrix

5.Simon Kunz's first big role in Four Weddings and a Funeral in 1994:

Closeup of Simon Kunz

After some small TV roles, Simon notably first appeared in Four Weddings and a Funeral alongside Hugh Grant.

Rank Film Distrubutors

Simon Kunz as Martin in The Parent Trap in 1998:

Closeup of Simon Kunz
Walt Disney Pictures

Simon Kunz now:

6.Kat Graham's first role as Jackie in The Parent Trap in 1998:

Closeup of young Kat Graham

Kat's very first onscreen credit was in The Parent Trap in 1998. Then, she appeared in shows like Lizzie McGuire, Hannah Montana, and more.

Walt Disney Pictures

Kat Graham now:

Closeup of Kat Graham

Kat's most notable role was as Bonnie Bennett on The Vampire Diaries. She starred on the series for 171 episodes. Recently, she's starred in movies like Operation Christmas Drop, The Holiday Calendar, and more.

Arnold Jerocki / GC Images / Getty Images

7.Maggie Wheeler's first notable role in Seinfeld in 1992:

Closeup of Maggie Wheeler in "Seinfeld"

After appearing in various TV shows, Maggie's first big role was on an episode of Seinfeld in 1992. Of course, she then went on to star on Ellen and Friends.

NBC

Maggie Wheeler as Marva Kulp Jr. in The Parent Trap in 1998:

Closeup of Maggie Wheeler
Walt Disney Pictures

Maggie Wheeler now:

Closeup of Maggie Wheeler

Maggie has gone to appear in countless shows like How I Met Your Mother, Archer, Curb Your Enthusiasm, and Shameless. In 2021, she reunited with the Friends cast for the Friends: The Reunion TV special.

Matt Winkelmeyer / Getty Images for Warner Bros. Studio Tour Hollywood

8.Hallie Meyers-Shyer's first role in Father of the Bride in 1991:

Hallie Meyers-Shyer in "Father of the Bride"

Hallie, who is the youngest daughter of Nancy Meyers, appeared in her mom's movie Father of the Bride in 1991 alongside her older sister.

Touchstone Pictures

Hallie Meyers-Shyer as Lindsay in The Parent Trap in 1998:

Hallie Meyers-Shyer in "The Parent Trap"

Fun fact: Hallie and Annie in The Parent Trap are named after Hallie and her sister Annie.

Walt Disney Pictures

Hallie Meyers-Shyer now:

Hallie Meyers-Shyer

In 2017, Hallie wrote and directed the movie Home Again starring Reese Witherspoon. She also wrote and directed the upcoming movie Goodrich starring Michael Keaton and Mila Kunis.

Amanda Edwards / Getty Images

9.Michael Lohan's first role as Lost Boy at Camp in The Parent Trap in 1998:

Michael Lohan in "The Parent Trap"

Michael appeared in The Parent Trap alongside his sister Lindsay Lohan. Also in The Parent Trap, Lindsay and Michael's other siblings and their mom appear at the airport in London.

Walt Disney Pictures

Michael Lohan now:

10.Polly Holliday's first major role in All the President's Men in 1976:

Screenshots from "All the President's Men"

After various small roles in TV and film, Polly's first big role was in All the President's Men in 1976. Then, she notably starred in Gremlins in 1984 as Ruby Deagle and in Mrs. Doubtfire as Gloria Chaney in 1993.

Warner Bros

Polly Holliday as Marva Kulp Sr. in The Parent Trap in 1998:

Closeup of Polly Holliday
Walt Disney Pictures

Polly Holliday now:

Closeup of Polly Holliday

Polly's retired from acting with her last movie being Fair Game in 2010 alongside Naomi Watts and Sean Penn.

Summit Entertainment

11.Ronnie Stevens's first notable role in The Avengers in 1961:

Closeup of Ronnie Stevens

Ronnie Stevens as Grandfather in The Parent Trap in 1998:

Closeup of Ronnie Stevens

Sadly, Ronnie died in 2006 at 81 years old.

Walt Disney Pictures

12.Joanna Barnes's first major role in Auntie Mame in 1958:

Joanna Barnes in "Auntie Mame"

Joanna Barnes as Vicki Blake in The Parent Trap in 1998:

Closeup of Joanna Barnes

13.And finally, Natasha Richardson's first major role in The Adventures of Sherlock Holmes in 1985:

Closeup of young Natasha Richardson

Natasha Richardson as Elizabeth James in The Parent Trap in 1998:

Closeup of Natasha Richardson

More on this