By Emily Hewitt
Happy Freaky Friday! Or rather, the Friday before Freaky Friday’s anniversary! Sunday, August 6 marks 20 years since the release of the charming film about a mother, played by Jamie Lee Curtis, and daughter, played by Lindsay Lohan, who switch bodies and come to understand each other better. Lohan captivated audiences years before and after Freaky Friday was released, cementing her as an icon among Disney viewers in the 1990s and early 2000s. Thus, D23 is celebrating this weekend with a nostalgic Lindsay Lohan watchlist.
1. Freaky Friday (2003)
Obviously, this is a must-watch. The classic comedy centers around Anna, an angsty teenager, played by Lohan, who is juxtaposed with Tess, Anna’s properly mannered mother, played by Curtis, which naturally makes for drama—and great comedy!—when they switch bodies. Playing both a rebellious teen daughter and overworked middle-aged mother shows the immense talent that Lohan and Curtis share. (The movie was a reimagining of the original 1976 Disney film with Jodie Foster as the daughter and Barbara Harris as her mom.)
The film showcases not only Lohan’s acting talents, but also her singing ability. The songs—such as “Ultimate” and “Take Me Away”—are nostalgic bops that are the soundtrack of youth for the Freaky Friday generation. (The film’s music is honored by a new, limited-edition D23-Member-exclusive pin just released.)
Even 20 years later, Lohan’s character, Anna, is still in the pop-culture zeitgeist with the soundbite “What? I’m ready” taking over TikTok. Her aughts style has even come back around, with her epic red-and-black, three-quarter-sleeve shirt being all the rage for younger Gen Z. Stream this classic comedy on Disney+ to hear the epic anthems and see the grunge styles that dominated screens in the early 2000s.
2. The Parent Trap (1998)
Long before Lohan switched bodies with Curtis in Freaky Friday, the two characters she plays in The Parent Trap switched lives. Playing one character who is a posh Londoner, named Annie, and another who is an edgy Californian, named Hallie, allowed Lohan to show her acting range at just 11 years old.
This film is the classic tale of twins who are separated as babies, only to reunite later in life—a story first told in the Disney classic 1961 film of the same name, starring Disney Legend Hayley Mills. Just as in the original, the twins are separated upon their parents’ divorce. In the 1998 rendition, winemaker dad Nick Parker, played by Dennis Quaid, lives with Hallie at his vineyard in Napa, California, while fashion designer mom Elizabeth James, played by Natasha Richardson, lives with Annie in Knightsbridge, a district of London, England.
The girls meet at summer camp and realize they are long-lost twins while sharing their mutual love for Oreos with peanut butter. They decide to switch places—after Annie teaches Hallie her signature handshake and Hallie pierces Annie’s ears—and spend the rest of the film trying to bring their parents back together, despite their dad’s recent engagement to soon-to-be evil stepmother Meredith Blake (Elaine Hendrix).
Although Lohan didn’t sing in this film—other than a snippet of “Let’s Get Together,” written for the 1961 film by Robert and Richard Sherman—the soundtrack is filled with classic songs such “Here Comes the Sun” by The Beatles and “This Will Be (An Everlasting Love)” by Natalie Cole. Get the peanut butter and Oreos out to stream this heartfelt film on Disney+.
3. Life Size (2000)
After stealing a book of spells to bring her mother back to life, tomboy football player Casey, played by Lohan, has her worst nightmare come true when a doll, a gift from her father’s co-worker, comes to life rather than her dead mother.
Now Eve, the life-size doll, played by Tyra Banks, must learn how to dress herself, cook, work a real job, and experience sadness for the first time. Although a doll, Eve doesn’t let the trials and tribulations dull who she is, as she breaks out in song at a corporate event and buys a wardrobe fit for a doll with a plethora of rhinestones and accessories for every look.
Despite Casey’s doubts, Eve proves to be just what everyone in the real world needs. She teaches Casey confidence and consoles her about her mother, gives the nerdy secretary at Casey’s dad’s office a 180-degree makeover so her office crush notices her, and brings Casey and her dad closer together.
Be sure to watch this life-sized film—and, most importantly, don’t forget to “shine bright, shine far, don’t be shy, be a star” just as Eve sings in the film.
4. Get a Clue (2002)
Those who live for high school gossip will soak up every part of this teen mystery. After Lexy Gold, played by Lohan, publishes a piece about the romance between two of her teachers, one of her teachers goes missing. Lexy must pair up with her three friends to solve the mystery via detective journalism.
Although her love of luxury goods seems like a useless perk of her family’s wealth, it ultimately helps Lexy solve the mystery from clues such as an overly dressed detective and a rare diamond broach.
The teen sleuths use an abundance of hidden cameras, sound-magnifying earpieces, and spyglasses that will remind people of their youthful spy days. If you haven’t already watched this film, “get a clue” and track it down on Disney+.
5. Confessions of a Teenage Drama Queen (2004)
After Mary Elizabeth “Lola” Cep, played by Lohan, moves to a New Jersey suburb from the Big Apple, she continues her dream of becoming a Broadway star and lands the lead role in her high school’s musical over rich mean girl Carla, played by Megan Fox.
Upon hearing the news that her favorite band, Sidarthur, are breaking up, Lola and her goody-goody best friend, Ella, go to New York City to see the band’s last concert. After a concert ticket mishap, they happen to run into the drunken lead singer, Stu Wolff (Adam Garcia), at a diner. They revive his declining life and later prove to Carla that they are indeed friends with the rock ’n’ roll icon.
This film introduced David Bowie music to Millennials and Gen Z with Lohan’s epic performance of “Changes” in her school’s musical, and it continues to allow people to dream of coincidentally meeting their favorite pop star. Thus it is an absolute must-see on Disney+.
6. Herbie: Fully Loaded (2005)
A beat-up Volkswagen Beetle, destined for the dump, isn’t what it seems to be in Herbie: Fully Loaded. Maggie, played by Lohan, is a recent college graduate—and as a graduation present, her dad (Michael Keaton) buys her this wreck of a car. If fact, though, it’s the magical Herbie—inroduced in Disney’s hit 1968 film The Love Bug—and it has a mind of its own! Herbie encourages Maggie, who comes from a racing family, to race a NASCAR champion, Trip (Matt Dillon). After getting her heart set on winning Trip’s shiny car in a race, Maggie instead loses Herbie to him and realizes just how much Herbie means to her.
The bond between a racer and their car is brought to light in this sports comedy. Stream it on Disney+ to see how much charm one car can have.
7. Just My Luck (2006)
A spin on the classic saying, Just My Luck follows Ashley Albright (Lohan), the luckiest girl in the world, who has taxis stop for her just seconds after lifting her hand and happens to get a dress belonging to Sarah Jessica Parker mixed up with her dry cleaning. In contrast, Jake Hardin, played by Chris Pine, is the unluckiest person in the world and the manager of an unsuccessful rock band, McFly. After Ashley and Jake kiss on the dance floor at a masquerade ball, their luck is switched. Ashley must now learn how to deal with inconveniences, while Jake’s success for McFly and himself comes fast and easy.
A romantic and comedic story ensues that leads Ashley to question what the cost is of her longstanding good luck. It would be just your luck to watch this film on Disney+ in celebration of Lohan’s epic career.