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The Parent Trap: Dennis Quaid, Lindsay Lohan & Cast Then & Now 20 Years Later – See Photos

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The beloved film starring Dennis Quaid and Natasha Richardson, ‘The Parent Trap‘ celebrated their 20th anniversary on July 20th.

The Parent Trap which gave actress, Lindsay Lohan her big break at the young age of 12 years old first debuted on July 20, 1998.  The film grossed 92M in box office sales and continues to be an iconic family movie.

What is the cast up to these days?  Keep reading to find out!

Dennis Quaid

Dennis played Nick Parker, a wealthy American winemaker and father to Annie and Hallie.  Quaid was 44 years old when the movie was made, which makes him 64 today.

Quaid has been married three times, to first wife PJ Soles, Meg Ryan, and Kimberly Buffington.  He is separated as of 2016.

Dennis has continued to act in such films as A Dog’s Purpose, I Can Only Imagine, and is slated to portray former President Ronald Reagan in an upcoming biopic entitled, Reagan due out 2019 summer.


Natasha Richardson

Natasha played Elizabeth James, a famous wedding gown designer and mother to Annie and Hallie.  Richardson was only 35 years old when filming the movie, 9 years Quaid’s junior.

Unfortunately, Natasha is no longer with us.  She passed away after a horrible skiing accident at Quebec’s Mont Tremblant Resort in Canada.  Natasha is sorely missed.

Dennis discussed Natasha on Megyn Kelly Today.

Lindsay Lohan

Lindsay played Hallie and Annie, twin preetens who were separated at birth.  Lohan played twins at the young age of 12.

Lohan was engaged to Dmitry Tarabasov from 2016 to 2017.

Lohan has continued to act starring in films such as Freaky Friday, Mean Girls, Labor Pains and Anger Management.  It appears she took a couple years hiatus from Hollywood but is back and scheduled to star as Katerina West in the UK comedy sitcom, Sick Note.


Simon Kunz

Simon played Martin, the James family’s butler, who falls in love with Chessy. Simon was 37 years old when he debuted as Martin.

Simon is currently married to his wife Briana who he has 2 children with.

Since starring in Parent Trap, Simon has acted in a number of shorts and TV series including Rosemary & Thyme, The Good Cop, and The Cave.  Coming up, Simon will be playing Herbert Quick in the TV series, Jerusalem.


Lisa Ann Walter

Lisa Ann played Chessy, the Parker family’s housekeeper, who meets and falls in love with Martin (played by Simon Kunz). Walter was 33 in the Parent Trap.

Walter was married and divorced in 1999 and has 2 children.

She has been quite active with acting appearing in shows like Las Vegas, Shall We Dance, and The Exes.  Coming up, Lisa Ann will appear in films “Remember Amnesia” and “TCB Baby.”


Elaine Hendrix

Elaine played Meredith Blake, a 26-year-old publicist publicist who is engaged to marry Nick Parker.  She was 27 when in The Parent Trap.

She is 5’8″ and is from Tennessee.

Elaine starred in a remake of “Get Smart” as Agent 66 with Barbara Feldon and Don Adams in 1995.  She has had many roles since The Parent Trap such as Two and a Half Men, The Client List, and Transparent.  Coming up, Elaine can be seen in Erase and TCB Baby.


Ronnie Stevens

Ronnie Stevens in The Parent Trap

Ronnie Stevens in The Parent Trap in 1998


Ronnie played Charles James, Elizabeth’s father and Annie and Hallie’s maternal grandfather.  He discovered Hallie on the phone with Annie.

Unfortunately, Ronnie is no longer with us either.  He was married to Ann Bristow for 47 years.  Ronnie and Ann both passed away in 2006.  He was 81 years old.

Catch ‘The Parent Trap’ on Freeform tonight, Monday July 23rd at 8pm EST.