Two decades ago, in 1999, the iconic teen movie 10 Things I Hate About You premiered. It arrived in a bumper year for high school rom-coms, with She’s All That, Notting Hill, Runaway Bride and Drive Me Crazy also hitting cinemas.
The sweetly raunchy movie introduced teenagers everywhere to the definition of “pensive,” the possibility of being just “whelmed” and the true purpose of black lingerie.
The film, based on Shakespeare’s The Taming of the Shrew, was also Heath Ledger’s breakout role.
Then a largely unknown Australian actor, Ledger played a high school bad boy who seduced the school's toughest cookie - and 'taught' her about love in the process, obviously...
In 2009 there was an attempt to recapture the rom-com's magic with a short-lived 10 Things I Hate About You TV show, but it lacked the chemistry of the original.
Twenty years later, the movie has stood the test of time, with strong female characters, the electric chemistry between Heath Ledger's Patrick Verona and Julia Stiles' Kat Stratford, and the ska soundtrack.
But what has the cast done in the two decades since the film hit cinemas?
Gabrielle Union
Gabrielle Union might be the most famous member of the 10 Things cast these days. At the time, she was reportedly nervous about the role as she was a decade older than her cast mates.
After 10 Things she continued in teen movies, starring in Bring It On in 2000. She went on to appear in films including Top Five and Cadillac Records and star in her own show on BET, the emotional Being Mary Jane.
In 2017, she released her memoir We’re Going to Need More Wine, which quickly became a New York Times bestseller.
She and her husband, Miami Heat player Dwayne Wade, welcomed their daughter Kaavia James in November of last year. Kaavia was born with the help of a surrogate, as the actress has been open about her miscarriages in the past.
Union also paid homage to Bring It On this Halloween, as she donned her iconic cheerleaders costume alongside her daughter Kaavia. She proved that once you’re a Clover, you’re always a Clover as she and her daughter both demonstrated their best cheer routines.
Union captioned one of her posts, “Brought it.”
Larisa Oleynik
Larisa Oleynik played Bianca, who’s not allowed to date until her older sister does. The only problem? Her sister has absolutely no interest in dating and is focused on attending Sarah Lawrence College instead. In a twist, Oleynik attended Sarah Lawrence in real life.
“I thought I probably wasn’t [going back to acting]. I didn’t study theater while I was there,” she said. “I just wrote a lot of really bad poetry,” the former child actress told Buzzfeed.
Apparently Oleynik originally auditioned for both Kat and Bianca, but was more interested in playing the feminist riot girl Kat. Instead, she ended up playing preppy Bianca.
She’s still best known for her role as Alex Mack on the Nickelodeon show The Secret World of Alex Mack.
Since 10 Things she's appeared in Mad Men and off-broadway theater productions. She lives in New York.
Heath Ledger
Heath Ledger’s breakout role was in 10 Things as Australian heartthrob and bad boy Patrick Verona, who was equally good at playing paintball and dancing in the bleachers. He went on to star in A Knight’s Tale, Brokeback Mountain, Casanova and most famously, The Dark Knight, which he won a posthumous Oscar for.
Ledger tragically died on January 22, 2008, at only 28, reportedly after accidentally overdosing from the prescription drugs he was taking.
He left behind a daughter, Matilda, with former girlfriend Michelle Williams.
Julia Stiles
Stiles, who was 17 at the time, played the “shrew,” or Kat, who was more interested in going to college than the boys at her school (which sounds pretty sensible to us).
The actress grew up in New York City and started working in commercials as a child, training at the New York Professional Children’s School.
Her career has been decidedly influenced by Shakespeare. She starred in an updated version of Hamlet in 2000 and a modern Othello called O in 2001.
She also starred in a Shakespeare-in-the-Park production of Twelfth Night in 2002. In later years, she co-starred with Matt Damon in the Bourne film series.
She graduated from Columbia University in 2005, where Anna Paquin was a classmate.
Her most famous role might be in the teen classic Save the Last Dance - a role she got after the director saw her in 10 Things. She’s still acting and is currently filming Hustlers alongside Cardi B, Jennifer Lopez and Constance Wu.
Stiles revealed that she was so in love with Hustler’s script that she had actually asked to meet with director Lorene Scafaria. Stiles told Glamour that she met with Scafaria and said, “My question is, what do I have to do to be in this movie?”
Eventually, Stiles landed the role of journalist Jessica Pressler and direct messaged Pressler on Instagram to do further role research. According to Forbes, Hustlers made $100 million worldwide as of October and stars including Jennifer Lopez are now tipped for an Oscar nomination.
She’s married to cameraman Preston Cook and they have a son named Strummer Newcomb Cook.
Joseph Gordon-Levitt
“If I’m really honest, I didn’t want to do a high school romantic comedy. I wanted to do Sundance movies. I’m very lucky that five years later, I got to do that. The truth is, I was a naïve or stuck-up 17-year-old,” Joseph Gordon-Levitt told The New York Times. The actor originally auditioned for both Cameron and Michael in 10 Things.
Gordon-Levitt went on to have a successful acting career, appearing in 3rd Rock from the Sun, 500 Days of Summer and Inception.
Andrew Keegan
Andrew Keegan appeared as the designated dreamboat on multiple ‘90s TV shows, including Party of Five and 7th Heaven.
In more recent years, he has founded his own spiritual organisation called Full Circle, which works to activate high vibes in California.
David Krumholtz
David originally wanted to play Cameron but ended up as his dorky best friend, Michael, who might have one of the best lines in the movie - “What is it with this chick? She got beer flavored nipples?”
He famously also starred in The Slums of Beverly Hills in 1999. He’s still acting and was most recently a voice in the animated movie Sausage Party. He also appeared in Harold and Kumar and Santa Clause.
He’s married to actress Vanessa Britting and they have two children.
Susan May Pratt
Pratt played the best friend in multiple teen movies, including Drive Me Crazy and Center Stage. She left home in Michigan to pursue modeling and ended up acting, but eventually went back to higher education. She attended Simon’s Rock College and Parsons School of Design and recently finished up the prerequisites for a master’s degree in occupational therapy at the University of Southern California.
Pratt guested on shows including Charmed and Mad Men but her post-teen rom-com career never truly took off. “It's kind of disappointing to have one's career peak in your mid-twenties and have it be a downhill slide since. [It’s] been hard for me in the last 15 years that my career has not progressed,” she told Buzzfeed.
She’s currently a mom and actress who still posts 10 Things stills and behind-the-scenes pictures on Instagram. She married fellow actor Kenneth Mitchell and they have two children, a son and daughter.
Nowadays, she reportedly has an acting rule - she won’t take a role unless she’s getting paid more than her babysitter.
Allison Janney
Who could forget Allison Janney's appearance as the romance novel writing Ms. Perky? Of course, she's had plenty of memorable roles since then, including in The West Wing, Veep and Mom.
