Rachael Leigh Cook's role as outcast Laney Boggs in the iconic 1999 teen rom-com "She's All That" is the reason so many rom-coms (and parodies of them) have adopted the classic trope of achieving an instant makeover simply by removing one's glasses. While 1999's "She's All That" may have been Cook's breakout role, she actually got her start as Mary Anne Spier in the 1995 adaptation of "The Baby-Sitters Club."
From cult classics like "Josie and the Pussycats" to recurring roles on TV shows like "Psych" and "Robot Chicken," Cook's proved her comedy prowess. It's easy to hate on "Josie and the Pussycats," but it's also one of those films you can rewatch and find something new to love each and every time — with Cook's Josie McCoy being one of the highlights. Although she's mostly known for her lighthearted roles, Cook has dabbled in the world of drama with 2007's "The Final Season" and the crime series "Perception" alongside Eric McCormack. In October 2022, she starred in "Spirit Halloween: The Movie," and more recently, she revisited the rom-com genre alongside Scott Ly in "A Tourist's Guide to Love," which hit Netflix on April 21. If you're looking for a dose of Rachael Leigh Cook nostalgia, go ahead and check out some of her best roles ahead.
Cook plays Mary Anne in this first onscreen adaptation of "The Baby-Sitters Club."
Cook plays Becky in "Tom and Huck," based on the works of Mark Twain.
The cast of "Carpool" includes Tom Arnold and Rhea Perlman.
The TV movie "Country Justice" also stars George C. Scott, Ally Sheedy, and Don Diamont.
"The Eighteenth Angel" is a horror film that also stars Stanley Tucci.
The ensemble cast of "Strike!" includes Kirsten Dunst, Gaby Hoffmann, Monica Keena, and Heather Matarazzo. The actors play students at a girls' high school in 1963.
"The Naked Man" stars Michael Rapaport as a chiropractor by day, wrestler by night.
"She's All That," the classic teen rom-com, put Cook on the map. Cook stars alongside Freddie Prinze Jr., Matthew Lillard, Paul Walker, Anna Paquin, Gabrielle Union, Dulé Hill, Clea DuVall, and Kieran Culkin. Usher plays a DJ in the film.
Cook stars in "Get Carter" with Sylvester Stallone, Miranda Richardson, Alan Cumming, Mickey Rourke, John C. McGinley, Michael Caine, and Rhona Mitra.
Cook stars in "Texas Rangers" with James Van Der Beek, Ashton Kutcher, Alfred Molina, and Dylan McDermott.
Cook stars in the British rom-com "Blow Dry" with Alan Rickman, Natasha Richardson, Rachel Griffith, Josh Hartnett, Bill Nighy, Rosemary Harris, and Heidi Klum.
Cook plays Josie in this iconic cult-classic film. Tara Reid and Rosario Dawson round out the title trio, with Alan Cumming and Parker Posey playing the villains.
Cook is in a love triangle with Melanie Griffith and Hugh Dancy in "Tempo."
The black comedy "11:14" stars Cook alongside Ben Foster, Clark Gregg, Colin Hanks, Shawn Hatosy, Barbara Hershey, Stark Sands, Hilary Swank, Patrick Swayze, and Henry Thomas.
"The Big Empty" stars Jon Favreau and features Cook a young woman who's attracted to Favreau's John.
Cook appears in this comedy thriller set in a college alongside Nick Stahl, Lukas Haas, and Johnny Galecki.
In "Stateside," Cook plays a woman struggling with schizophrenia. The movie also stars Val Kilmer and Carrie Fisher.
The miniseries "Into the West" tells a generational story about one white and one Native American family during the American expansion into the west. The show has an enormous cast, with over 250 speaking parts.
In the direct-to-video film "My First Wedding," Cook plays a woman who fantasizes about every man she meets. She confesses to a priest (Kenny Doughty), who turns out to not actually be a priest. Hijinks ensue.
In 2007's "Nancy Drew" starring Emma Roberts, Cook plays the secret daughter of a dead movie star.
"Blonde Ambition" stars Jessica Simpson as a model who ends up working her way up the corporate ladder. The cast includes Luke Wilson and Willie Nelson.
Cook stars in this comedy film alongside Luke Kirby and Lisa Ray.
Cook stars in the baseball film "The Final Season" alongside Sean Astin.
For two years, Cook appeared on the long-running USA comedy "Psych." She plays the high-school crush of Shawn (James Roday).
Cook starred in all three seasons of TNT'S "Perception." She plays an FBI agent who teams up with neuropsychiatrist Dr. Daniel J. Pierce (Eric McCormack).
Cook stars in the Hallmark movie "Summer in the Vineyard."
Cook continued her streak of Hallmark romances with 2018's "Frozen in Love."
"A Blue Ridge Mountain Christmas" was Cook's first Christmas Hallmark film.
Cook stars in the legal rom-com "Love, Guaranteed" alongside Damon Wayans Jr. Attorney Susan (Cook) represents Nick (Wayans) in a lawsuit against a dating app that "guarantees" you'll find love.
Cook stars in the horror movie "Spirit Halloween: The Movie."
Cook stars as a travel executive who, after the end of a long-term relationship, travels to Vietnam to scope out travel destinations undercover. Everything changes when she winds up falling for a local (Ly).