In 1998, Lindsay Lohan got her big break with the remake of this Disney classic. In the film, she plays both Annie and Hallie Parker, twins who were separated at birth and raised by either their father or mother. The two meet at summer camp and make a plan to get their parents back together...by switching places.
Life-Size was a TV movie from 2000 that showed what happens when a girl who misses her dead mother tries to resurrect her but accidentally brings her doll Eve (Tyra Banks) to life instead.
Thanks to Get a Clue, Disney Channel kids learned what it takes to become a spy...sort of. In the DCOM, Lohan plays Lexy Gold, a fashionable and wealthy student who teams up with her friends for the school newspaper to solve the case when their teacher goes missing.
With the success of The Parent Trap, Disney tapped Lohan again—this time to take on the 2003 update of the Jodie Foster body-swap flick that found the spunky 17-year-old successfully making us believe she really was Jamie Lee Curtis.
In 2004, the starlet showed off her comedy chops as an adolescent dealing with such seemingly life-or-death challenges as popularity and getting the lead role in a high school play.
So fetch! This 2004 hit film brought Lohan's fame to a whole different level and now girls (mean or nice) want to buy army pants and flip flops and channel their inner Cady Heron AKA the home-schooled jungle freak turned popular Plastics member.
Lohan returned to her Disney roots to help the studio revive its famous Love Bug franchise in 2005 and she looked good as a race car driver.
After running into Jake (Chris Pine), a man down on his luck, Ashley (Lohan) realizes that her lucky streak has been transferred to him inadvertently, leaving her without any luck in this 2006 rom-com.
Rachel (Lohan) is sent to live with her grandma Georgia (Jane Fonda) by her mother Lilly (Felicity Huffman) for the summer and as she tries to follow her grandma's rules she also has to keep a secret that could ruin her family dynamic forever.
The redhead star played a much darker role—or roles, rather—in this mistaken-identity thriller, showing her range as an actress.
In 2008, the New York City native appeared as a guest star on four episodes of Ugly Betty as Kimmie Keegan. Throughout her time on the show, Kimmie, Betty's (America Ferrera) high school bully and eventual assistant proves she can't be trusted and burns a lot of bridges before being fired from Mode magazine.
Lohan showed off another side of her acting skills when playing April, a party girl dressed in a nun's outfit who can shoot to kill, in this action flick in 2010.
It was drama for days, darling, when Lohan as Elizabeth Taylor butted heads with Grant Bowler's Richard Burton in this Lifetime biopic.
The actress played herself in the fifth installment of the Scary Movie franchise and her screams were on point.
In this 2013 thriller, Lohan played Tara in Christian's (James Deen) latest film project, who has a secret affair with his lead Ryan (Nolan Funk), which leads the film maker and trust-fund kid to use cruel mind games and violence in order to seek revenge.
Lohan joined the cast of Sick Note in 2018 playing the daughter of Daniel Glass' (Rupert Grint) boss. After a cancer diagnosis turns out to be false, Daniel decides to keep lying to everyone so his life remains in its current, happy state instead of the rubbish one he had before the cancer fake out. Sadly, those lies do catch up with him and Lohan's character doesn't exactly fall for his consistent falsities.