Fiona Montgomery (Jennifer Coolidge) is a villainess from the 2004 teen comedy A Cinderella Story. She was the stepmother of protagonist Sam Montgomery and the mother of Brianna and Gabriella Montgomery.
As revealed in the movie's prologue, Fiona met Hal Montgomery, Sam's father, during the girl's birthday party. At the time, she had a much less glamorous appearance than her future self, wearing glasses and less expensive clothing. She and Hal soon became married, and the first hint of her true personality came out when she insisted only one wedding photo, disregarding the fact that Sam had not been in the shot. When the Northridge Earthquake struck, Hal was taking shelter with Sam in her bedroom door frame when Fiona cried out for help. Hal went to help her, and was subsequently killed. Hal had left Sam the family house and diner in his will, but the evil Fiona kept it hidden from Sam and took ownership of both, while also having Sam's new bedroom be in the attic.
Eight years later, Sam was a high school senior and Fiona was treating her as her personal slave, ordering her around both at home and having her work extensive shifts at the diner (which she had renamed Fiona's). In the years since her husband's death, she has also begun flaunting her wealth around with lavish clothing, manicures, and keeping her lawn constantly watered (despite there being a drought). Despite Sam's misery under Fiona's rule, Sam obeyed her so she would fund her education for Princeton. On the day of her school's Homecoming, though, Sam begged Fiona to let her take off her late night shift so she could attend the dance and meet "Nomad", the guy she had developed a relationship with online through a Princeton chat room. Fiona still said no and coldly told Sam she wasn't pretty or smart.
Later that night, at the diner, Fiona rudely bumped into Sam and got into a fight with Rhonda, her head waitress. After the dance, Fiona (now with a botoxed face) was disappointed that Brianna and Gabriella had not won anything and became irritated when they wanted her to rush to the diner, having learned that Sam was at the homecoming dance. But by the time they arrive there and Fiona started to get suspicious, Sam appeared with her uniform on over the dress she borrowed by Rhonda. Later on, when Fiona found Sam's acceptance letter from Princeton in the mail, the villainess discarded it as a way of keeping Sam working at the Diner and as her slave forever. She later gave Sam a doctored one of rejection and callously disregarded Sam's heartbreak. Later on, though, after being reminded of her father's favorite mantra ("Don't let the fear of striking out keep you from playing the game"), Sam stood up to her evil stepmother and declared that she was quitting her job and moving out and was tired of all the emotional abuse. Rhonda also stood up to Fiona and told her that she quitting as well, including the rest of the staff, who had only put up with Fiona's abuse for so long to be there for Sam. Rhonda briefly scared the cowardly Fiona before leaving along with the rest of the employees and customers.
Later on, Sam found her father's will in the fairytale book from her childhood which stated that the house, the diner and everything belonged to her. Since this leaves her as the rightful and legal owner, Sam sells her stepfamily's fancy cars so that she can pay for college, and Fiona, who signed the will as a witness but claims to have never seen it before, is arrested for financial fraud and violating California's child labor laws for all the times she made Sam work long hours at the diner in spite of her being a minor. Fiona, Brianna and Gabriella are made by the District Attorney to work off the money they stole from Sam at the diner, which is restored to its former glory by its new owners, Sam and Rhonda.
- Fiona was one of four villainesses in A Cinderella Story--the others being Shelby Cummings and her evil daughters Brianna and Gabriella.
- Jennifer Coolidge later appeared as the evil Angie Serabian on The Closer.