An instant classic in the genre of teenage rom-coms, 10 Things I Hate About You restyled Shakespeare’s The Taming of the Shrew in a modern setting with fresh characters. Set in a 1990s high school, the modern “shrew” is Kat Stratford, the daughter of an obstetrician with helicopter parenting techniques. Kat is the stark opposite of her social butterfly of a younger sister, Bianca, who is not allowed to date until Kat does. Bianca’s multiple suitors then invest into Kat’s love life, paying the ill-reputed Patrick Verona to successfully woo the notoriously difficult older sister.
MOVIEWEB VIDEO OF THE DAY
8 Allison Janney - Mrs.Perky
Allison Janney played the high school principal by day, smutty novel writer by… well, day as well. Though Janney had relatively low screen time, with she herself admitting that she forgets she was in the film, Mrs. Perky stood out as a quirky and unforgettable character. Since the film, she has starred in West Wing, I, Tonya, and Mom. Today, Janney can be found gracing your screen as the titular character in Lou, a role that has made her an action hero at the age of 62. She also stars in the recent release of The People We Hate at the Wedding.
MOVIEWEB VIDEO OF THE DAY
MOVIEWEB VIDEO OF THE DAY
MOVIEWEB VIDEO OF THE DAY
7 Gabrielle Union - Chastity
The seemingly ageless beauty, who made her debut in the 1999 films 10 Things I Hate About You and She’s All That, remains an influential figure today. Her work in advocating against domestic violence, women’s health, and violence against women has earned her much recognition, including being named on of Time magazine’s 100 Most Influential People in 2020. She has also garnered attention for her marriage to NBA player Dwayne Wade, with whom she shares one child and is step-mother to his three. Together, they have openly provided encouragement and support to Wade’s daughter transgender Zaya, defending her identity against media and internet criticism. She has recently starred in Girls Trip and the 2022 release of Cheaper By the Dozen.
6 Andrew Keegan - Joey Donner
Andrew Keegan played the handsome but unlikeable Joey Donner, a teenage Casanova desperate to date Bianca Stratford. Following the success of 10 Things I Hate About You, Keegan starred in a number of projects, none of which reached critical or notable commercial success. Seemingly venturing into a new path, Keegan founded Full Circle, an LA-based spiritual community center. While some media sources chided the center as a cult, all reports seem to indicate it is simply a non-religious center for people of all faiths to practice yoga, meditation, and the like.
5 David Krumholtz - Michael
After a number of moderately successful starring roles, including a lead role that was only released on DVD, David Krumholtz returned to the formula that worked best in his career; notable supporting roles in successful titles. Such projects in the past decade include This is the End, The Judge, and Sausage Party. Evidently a fan of unexpected career moves, Krumholtz recently released music under the name Beengod Stillgod in collaboration with the group Hemoglobin. His artist profile has zero monthly listeners, while Hemoglobin has 40.
4 Larisa Oleynik - Bianca Stratford
Larisa Oleynik was in a position to launch a career as a new America’s sweetheart, as a character that quips “I happen to like being adored, thank you!”. Following the success of the film and a successful run as a child star, Oleynik’s career seems to have suffered a bit of a lull. Despite this, she re-emerged in the 2010s with recurring roles in Mad Men and Hawaii Five-O. Little is known about her personal life, with her Instagram account being private.
3 Joseph Gordon-Levitt - Cameron James
Having already established a name as a child star, 10 Things I Hate About You was merely another notch on Joseph Gordon-Levitt’s belt; one he initially didn’t really want. The star briefly took a break from acting to study at Columbia University, during which time he lived in the same dorm hall as and dated his 10 Things I Hate About You co-star, Julia Stiles. After dropping out to pursue acting again, Gordon-Levitt steadily built up a formidable resume in the 2000s, culminating with his acclaimed leading role in The Lookout. One of his more notable roles was as Tom Hansen in 500 Days of Summer, a performance that earned him a Golden Globe nomination. He subsequently starred opposite Leonardo DiCaprio in the hit film Inception, further solidifying his A-List status. He is happily married to the Founder and CEO of Fellow Robots, Tasha McCauley, with whom he has two children.
2 Julia Stiles - Kat Stratford
1 Heath Ledger - Patrick Verona
Lastly, we have the iconic and dearly missed, Heath Ledger. Following his role as Patrick Verona, the Australian actor went on to pay his dues and build his credentials with a number of supporting roles opposite established stars. These gave way to leading roles in films such as A Knight’s Tale and The Brothers Grimm. In 2005, Ledger received wide critical acclaim and an Academy Award to boot for his role in Brokeback Mountain, a socially pioneering film that opened the doors for greater inclusivity for the LGBT community on screen. The movie effectively etched Ledger’s name into film history, establishing him as a formidable and respectable leading man. One of his final roles was as the iconic Joker in The Dark Knight, a role for which he received a posthumous Academy Award.
On January 22, 2008, Ledger passed away from an accidental overdose of a range of prescription medications. Family and friends confirmed that the actor suffered from a respiratory illness and sleeping problems, which likely prompted the drug abuse. He was survived by his daughter, Matilda.
