Lindsay Lohan’s Freakier Friday is on its way, and the legacy sequel has one surprising reunion that wonderfully pays off another movie. Freaky Friday is one of Hollywood’s greatest feats in body-swap comedies and has since become a household name. The upcoming sequel to the original 2003 movie will bring Anna and Tess (Jamie Lee Curtis) back to the big screen, and reunite the beloved cast of Freaky Friday. Although the sequel, expected for August 8, 2025, has only just gotten a trailer, we have a considerable amount of information to work with — including Lohan’s reunion with several stars.

One of the biggest names of the early 2000s, plenty of stars of Lindsay Lohan’s movies became major hits during the period between the late 1990s and early 2000s. Lohan has something of a unique experience in Hollywood, growing from a prominent child actor to a young adult in the industry before a string of comeback movies. Although she is an incredibly versatile performer, one of her most cherished movies is the iconic rom-com from the late 1990s. Now, a familiar face from The Parent Trap will be seen alongside Lohan again, as a previous co-star appears in Freakier Friday.

The Parent Trap’s Elaine Hendrix Is Reuniting With Lindsay Lohan In Freakier Friday

Hendrix Momentarily Appears In The Freakier Friday Trailer

Disney’s trailer for Freakier Friday reveals plenty of exciting details, elaborating on the premise of the beloved original movie. The short teaser opens with returning characters, Anna and Tess, who are forewarned by a clairvoyant that their lives will cross again. Of course, this sets up the succeeding four-way body swap. Freakier Friday introduces two more teenage stars and has an array of other major stars attached to the project. Not only will Lohan reunite with Chad Michael Murray, reprising his role as the love interest, Jake, but she will also reunite with former co-star Elaine Hendrix.

Hendrix briefly appears in the new trailer for Freakier Friday, a blink-and-you’ll-miss-it moment. Hendrix can be spotted in the final thirty seconds of the trailer, dressed as a waitress and rolling her eyes at something off-screen, standing beside Maitreyi Ramakrishnan. Hendrix previously played Meredith Blake in The Parent Trap remake alongside Lohan. Blake is the main antagonist of The Parent Trap and plans to marry Nick (Dennis Quaid) for his wealth. Freakier Friday is sure to make use of nostalgia, coming 22 years after the original, but this reunion makes the upcoming legacy sequel all the more exciting.

Will The Parent Trap Ever Get A Disney Sequel?

It’s Unlikely The Parent Trap Will Be Remade Despite Hollywood’s Trend

There are no prospects of a sequel to the legendary film for several reasons. The tragic death of The Parent Trap star, Natasha Richardson, would likely factor quite heavily into the decision. Richardson was a large part of the original movie, and it’s difficult to imagine how Disney could continue without her — both for the story and to preserve her legacy. Not to mention, the story’s scope is limited to the twins exchanging roles. Unlike Freakier Friday, the film is somewhat confined to the twins and leaves minimal room for the involvement of additional characters in the comedic chaos.

That being said, Hollywood has become more inclined towards sequels in recent years. The rapid speed at which the industry is changing direction has been skeptically received, and sequels can be seen to have dominated the big screen in 2024. While some unfortunate conditions make the production of The Parent Trap unlikely, it doesn’t mean that a remake can be completely ruled out. Disney regularly returns to its popular properties because it generates mᴀss amounts of nostalgia. In short, sequels have become a surefire strategy for success and, like Freakier Friday, The Parent Trap could fall victim to this Hollywood trend.