Before the turn of the new millennium, a movie came out featuring a star-studded cast that brought some of them into the spotlight in the 2000s. 1996 saw the Shakespeare classic Romeo & Juliet being adapted into Romeo + Juliet, featuring a modernized setting with Leonardo DiCaprio and Claire Danes as the two star-crossed lovers. Three years later, one of Shakespeare's comedies, Taming of the Shrew, would get the modern treatment. With Gil Junger debuting as the director and Julia Stiles, Heath Ledger, and Joseph Gordon-Levitt as part of the main cast for 10 Things I Hate About You.

There were a lot of memorable scenes that are still quoted to this day, and the performances of the three actors have gained breakthrough status. The romance between Ledger and Stiles' characters were praised alongside their chemistry onscreen. With the movie's cult status, it has celebrated its anniversaries. As we look back on Ledger and Stiles' relationship behind the scenes, we shall also go over their time as actors before appearing in 10 Things I Hate About You and then Stiles' thoughts on the late actor years later.

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What Happened Between Julia Stiles And Heath Ledger?

Before Stiles and Ledger appeared in 10 Things I Hate About You, the two had other film credits before gaining recognition for their breakthrough performances as Kat Stratford and Patrick Verona. Stiles had her first film debut in the 1996 romantic drama I Love You, I Love You Not and her first leading role in the 1998 thriller Wicked as Ellie Christianson. Ledger appeared in Australian TV shows and movies before moving to the United States in 1998. A year earlier, he earned his first film credit in the teen drama Blackrock. While he did make appearances in earlier works, Blackrock is considered to be his first major film credit as it helped him gain recognition.

It would be impossible to not picture Stiles and Ledger as the two leads, but Ashton Kutcher and Josh Hartnett were also considered in playing Patrick, while Katie Holmes or Kate Holmes could have been cast as Katarina. With Stiles and Ledger taking on the roles, they received critical praise and earned many nominations from the Teen Choice Awards, MTV Movie Awards, and Young Star Award.

Related: Julia Stiles Reveals Sweet Moment With Heath Ledger In '10 Things I Hate About You'

Heath Radiated Endearing Energy

People reported Stiles looking back on working with the late actor, joining in their podcast to discuss her time with Ledger. Stiles recalled Ledger being extremely gracious and giving her the spotlight when her scenes involving him came in. In her episode of People in the '90s, she added, "I remember Heath Ledger was so gracious about the whole thing. I appreciate this so much more now, having worked more. He wasn't trying to compete with me. He stood back, and he was like, this is your scene." His courtesy was consistent while filming their scenes together. Stiles also stated, that "When they did his reaction shot, he didn't well up. He didn't go, 'OK, now I have to do something with my side of the camera.' He was just like, 'That was beautiful, and this is your scene.'"

And that doesn't stop there for Stiles praising her costar. He blew her and the cast's mind when he showed off his captivating singing when he started shooting his famous scene. "You know, he had his amazing moments in the movie, too — the singing and dancing and running up and down those steps," Stiles commented. "But he was confident enough, even just starting out, to be like, 'I'm handing over the stage to you.' And I learned way later in life that that doesn't always happen."

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Things Changed For Julia Stiles Today

It has been almost 14 years since Ledger's tragic passing, and as the rest of the cast have progressed onward towards their respective careers, they and especially Stiles have kept her positive experience with Ledger close to her heart. Stiles continues to do acting to this day, though her roles have been more focused on side characters, though it doesn't stop her from still being successful. Her upcoming movie Orphan: First Kill, has an unknown release date, but it's possible it can come out this year. In January 2022, Stiles announced that she has given birth to her second son named Arlo. She and her husband Preston J. Cook welcomed their first son Strummer in 2017 and have been a loving and growing family since their marriage the same year. So for now, she is currently in mama mode taking care of her second son.

If you have not seen 10 Things I Hate About You, now is a good chance to do so as it is currently free to watch on YouTube. It can also be streamed on Disney+, Amazon Prime Video, Apple TV, and Roku to name a few.

Next: What The Cast Of 'The Dark Knight' Has Said About Working With Heath Ledger