The (Understandable) Conditions Lindsay Lohan Has Before Joining A Parent Trap Sequel

11-year-old Lindsay Lohan as twins Annie and Hallie in The Parent Trap (1998).
(Image credit: Walt Disney Pictures)

Lindsay Lohan celebrated turning 40 years old last month, and it’s hard not to believe how much time has passed since her first feature film, Nancy Meyers' 1998 version of The Parent Trap. The Mean Girls actress has been reflecting on her nearly three-decade career in Hollywood, including the iconic family rom-com that launched her career. Lohan recently had the chance to briefly revisit her Parent Trap characters, twins Annie and Hallie, for a brand deal, and revealed the understandable conditions she has before joining a full-fledged sequel.

The Freaky Friday actress returned to her roots (literally) in her Reeses-Oreo commercial, once again stirring up wishes for a Parent Trap sequel. While there is no confirmation in the commercial itself, other than a wink from Lohan, it’s highly implied she’s playing Annie and Hallie. Lohan told Us Weekly she wouldn’t fully return as the mischievous twins without seeing a script first, and revealed the one other condition she has before signing on to a follow-up:

And [after I] talk to Nancy Meyers, out of respect to her, because she’s phenomenal and made a great movie in The Parent Trap that we did together.

Ever since the Just My Luck actress set the Lohanissance into motion with Freakier Friday, a sequel to her 2003 hit Freaky Friday with Jaime Lee Curtis, fans have been clamoring for a Parent Trap reprisal. The beloved '90s film marks Meyers' directorial debut, and boy did she set the bar high. A sequel to the movie, which is a remake of the 1961 movie of the same name starring Hayley Mills, has been brought up before to several cast members to mixed reactions.

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Lisa-Ann Walter, who plays Chessy, previously pitched a sequel idea but, like Lohan, she said she would only sign on if Meyers were attached to the project. Given Elaine Hendrix (Meridith Blake) makes a cameo in Freakier Friday and is still good friends with Lohan and Walter, I'd also hope that she would be open to returning if a sequel were to come to fruition.

However, the hesitation for nearly all of the cast, but especially Dennis Quaid (who plays Annie and Hallie’s father Nick Parker), is the absence of Natasha Richardson. The actress, who plays the twins’ mother Elizabeth James in the movie, tragically died in 2009 due to a skiing accident. Quaid has said a number of times that while he would love to do a Parent Trap sequel, Richardson is "irreplaceable" and, therefore, a sequel without her would be impossible.

Richardson is unfortunately not the only Parent Trap cast and crew to have died in the 28 years since the film came out. More recently, Polly Holliday, who plays Camp Walden leader Marva Sr, died last year, with Meyers, Lohan, Walter, and more penning sweet tributes to the late great actress.

As someone who rewatches The Parent Trap annually with my Disney+ subscription, I’m hesitant to support a sequel. It’s such a comfort movie for me, and 11-year-old Lohan’s incredible dual performance brings so much life to the film. But so does the chemistry between Quaid and Richardson, and it wouldn’t be the same without the former. It’s one of those instances where I like how the movie stands, as is. Let's be honest, not every movie needs the sequel treatment.

However, as a fan, I did absolutely love Lohan’s Reeses-Oreo collab, which was the perfect dose of nostalgia for my Parent Trap heart. The ad -- directed by Patricia Arquette and co-starring Lohan and comedian Amy Sedaris -- takes excellent advantage of the infamous dipping of Oreos in peanut butter made famous by The Parent Trap. Check it out:

REESE’S OREO® Two Fated Icons Starring Lindsay Lohan - YouTube REESE’S OREO® Two Fated Icons Starring Lindsay Lohan - YouTube
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While I’m not entirely on board for a Parent Trap sequel, I could get behind another modern remake. That seems to be the pattern with this beloved screenplay, and I’m absolutely not opposed to some cameos from Lohan and her 1998 co-stars. Still, with legacy sequels being so popular right now, it wouldn't be surprising if Lohan were to touch base with Meyers and get a follow-up off the ground.

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