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The movie, a remake of a '60s film with the same title, was directed by Nancy Meyers and went on to earn millions worldwide. "The Parent Trap" was also the first film Lindsay Lohan starred in and it paved the way for her roller-coaster Hollywood career.
Keep reading to see what the cast has been up to since the "The Parent Trap" made its big screen debut 22 years ago.
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Lindsay Lohan starred as long-lost sisters Annie and Hallie.
Lindsay Lohan's "The Parent Trap" body double was played by Erin Mackey.
Walt Disney Pictures
Lohan returned to the spotlight in 2019 with her MTV reality show "Lindsay Lohan's Beach Club."
Lindsay Lohan in January 2019.
Slaven Vlasic/Getty Images
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Dennis Quaid played Hallie's dad, Nick Parker.
Dennis Quaid began snagging acting roles in the '70s.
Walt Disney Pictures
Quaid still acts, but he's also a musician.
Dennis Quaid in January 2020.
Jeff Spicer/Getty Images
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Annie's mom, Elizabeth James, was portrayed by Natasha Richardson.
Natasha Richardson's first credited role was in the film "Every Picture Tells a Story."
Walt Disney Pictures
Richardson passed away in March 2009 after a skiing accident.
Natasha Richardson attended a gala in New York City in February 2009.
Larry Busacca/Getty Images North America
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Meredith Blake was played by Elaine Hendrix.
Meredith Blake was a bit of a diva in "The Parent Trap."
Elaine Hendrix in The Parent Trap/Buena Vista Pictures Distribution
Hendrix has appeared in several movies and TV shows since, but she's also outspoken about animal rights.
Elaine Hendrix in March 2019.
Frederick M. Brown/Getty Images for KNK Productions, Inc.
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Chessy, Nick and Hallie's housekeeper, was played by Lisa Ann Walter.
Chessy was like an extended member of the family in "The Parent Trap."
Walt Disney Pictures
Following "The Parent Trap," Walter landed roles in "Bruce Almighty" and "Shall We Dance."
Lisa Ann Walter in January 2020.
David Livingston/Getty Images
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Simon Kunz portrayed Elizabeth and Annie's loyal butler, Martin.
Martin and Annie had a complex, special handshake that they performed before he dropped her off at camp.
Walt Disney Pictures
Simon Kunz has appeared on British series, like "Sherlock" and "Coronation Street."
Simon Kunz played Sir Edwin on "Sherlock."
BBC America