Lizzie McGuire and More: Relive Hilary Duff's Most Memorable Roles Over the Years

While most consider another role on this list as Hilary Duff‘s debut, her first lead role actually came in this 1998 direct-to-video sequel to the 1995 film Casper, playing the classic Harvey Comics character (and Casper the Friendly Ghost BFF) Wendy the Good Little Witch. Duff was only 10 when the film was released.

It wasn’t until this Disney Channel series, which debuted nearly two decades ago on January 12, 2001, that Duff became a household name, starring as the beloved titular teenage character while also voicing the animated version that expressed Lizzie’s inner thoughts and emotions. The series ran aired 65 episodes through February 14, 2004 and even got a feature film in 2003 that followed Lizzie on a school trip to Rome. Duff will return to the character for a highly-anticipated sequel series debuting on Disney+ in 2020.

A year after becoming a Disney Channel fixture, Duff starred opposite Even Stevens star Christy Carlson Romano in her first DCOM, playing Kelly Collins, a free-spirited and fashion-forward eighth grader forced to enroll at her hew new stepfather’s military academy.

Duff joined Malcolm in the Middle star Frankie Muniz in this 2003 spy comedy about a 15-year-old who goes undercover for the CIA, playing the daughter of a scientist employed by an evil organization that the intelligence agency wants intel on. The film marked her first major motion picture, hitting theaters two months before The Lizzie McGuire Movie. A sequel was released a year later, however she did not return.

For her third theatrical release of 2003, Duff co-starred as Lorraine Baker, one of 12 children raised by Steve Martin and Bonnie Hunt in this family comedy, a remake of a 1950 film of the same name. She returned as Lorraine two years later in the sequel Cheaper by the Dozen 2.

In 2004, Duff starred in this modern take on the Cinderella story, playing Sam Montgomery, with Chad Michael Murray as her “prince” aka her anonymous online pen pal and quarterback of the football team and Jennifer Coolidge as her evil stepmother Fiona. The film was a hit and spawned four sequels—three direct-to-video and a fourth for Freeform—with Selena Gomez, Lucy Hale, Sofia Carson and Laura Marano following in her footsteps.

That same year, she starred in this musical drama as Terri Fletcher, a teenager grieving the death of her brother (played by Jason Ritter!) who travels to Los Angeles from her small town to spend the summer in a music program against her father’s wishes. Naturally, he find out and things get very dramatic.

In 2006, Duff co-starred opposite her older sister Haylie Duff in this film loosely based on Jane Austen‘s Sense and Sensibility as two rich and spoiled Hollywood socialiate sisters, heiresses to their family’s cosmetics fortune, who given the ultimate wake-up call when a scandal involving the company’s night cream strips them of their wealth. It’s not the most beloved film in her oeuvre, but a campy delight nonetheless. 

Two years later, she appeared in this political satire co-written and produced by star John Cusack as a risque Central Asian pop star (and secret daughter to Ben Kingsley‘s hitman Walken) hilariously named Yonica Babyyeah. Again, not exactly the most beloved film.

In 2009, Duff returned to TV with a six-episode stint on the CW hit as Olivia Burke, a movie star who inexplicably strikes up a relationship with Penn Badgley‘s Dan after enrolling at NYU and becoming roommates with Jessica Szohr‘s Vanessa. The trio memorably had a threesome before Olivia, realizing Dan had feeling for Vanessa, ended things.

It wasn’t until 2015, however, that she returned to TV in a major way, starring as literary editor (and eventual publisher of her own imprint) Kelsey Peters on the hit TV Land rom-com, heading into its seventh season later this year.