The Parent Trap Cast, Then and Now

01 of 06

LINDSAY LOHAN

Looking back at her time filming the cult-classic movie, Lohan — who flawlessly played two characters, twins Hallie and Annie, in the 1998 remake — told Vanity Fair she'd tell her younger self to "put yourself first and just breathe." She continued, "Be happy and always be grateful for the moment you have in front of you. Be here, now." Lohan, who traded Hollywood for a low-key life in Dubai, is less about acting and more about flexing her entrepreneurial muscles these days. She has opened two nightclubs in Greece.

02 of 06

DENNIS QUAID

Quaid — who played Hallie and Annie's dad, Nick Parker — has only fond memories of working with Lohan on The Parent Trap. "Meeting her and you just knew this was her very first thing," Quaid recounted. "She was so natural. She was just so believable." The actor continues to act, and most recently starred in 2018's I Can Only Imagine.

03 of 06

NATASHA RICHARDSON

Starring as the eponymous fashion designer behind label Elizabeth James, Richardson served as Hallie and Annie's mom, who the girls were desperately trying to reunite with their father (Quaid). Sadly, a little over a decade after her turn in The Parent Trap, the Maid in Manhattan actress died of blunt force trauma after falling while skiing at Quebec's Mont Tremblant. She is survived by husband Liam Neeson and their two sons Michéal and Daniel, who were 13 and 12, respectively, at the time.

04 of 06

ELAINE HENDRIX

Every movie needs a villain and Hendrix's Meredith Blake — who was after the twins' dad and his fortune — had that honor in The Parent Trap. "Right after the film came out, I [misguidedly] got it in my head that I didn’t want to be 'stereotyped,' so I turned down a lot of chances to play other roles like [Meredith]—even though I did play some," Hendrix admitted to Backstage. "That was a silly move. Now I wish I had taken every single role like her I could and cornered the market on 'bitch,' which is so fun to play. Live and learn."

05 of 06

LISA ANN WALTER

Not only was Chessy (Walter) the Parker's longtime trusted housekeeper, but she also served as everyone's confidante, including the twins' as they conspired to get their parents together again with her help. Since starring in the fan-favorite role, Walter has appeared in Bruce Almighty and Netflix's Glow. And if you're looking to get your mind blown, get this: Walter and Hendrix — who played Nick Parker's horrid love interest— are real-life BFFs.

06 of 06

SIMON KUNZ

Elizabeth James' butler Martin (Kunz) had Annie's back as much as Chessy (Walter) had Hallie's, so it came as no surprise when Martin and Chessy eventually fall in love, providing every '90s kid watching The Parent Trap with the ultimate relationship goals. Since Kunz's Martin and Annie taught us the proper way to greet someone, the actor has transitioned to TV work. He recently wrapped up filming on Requiem.