It’s been 25 years since 10 Things I Hate About You hit theaters. Julia Stiles still remembers that audition like it was yesterday.

The 43-year-old actress, who was just 17 at the time, was relatively new to Hollywood. She had landed roles in prior films like The Devil’s Own starring Brad Pitt and Wide Awake directed by M. Night Shyamalan. She even starred in the Sundance-bound thriller Wicked, a role she won over fellow ’90s actresses Rachael Leigh Cook and Katie Holmes. Stiles wasn’t doing bad at all for a high school senior, but she was still awaiting her breakthrough role.

10 Things I Hate About You was exactly that.

“That was my first big movie,” Stiles told Yahoo Entertainment. “I was a 17-year-old auditioning actress. So I’m trying to figure out who I am as a person, and then also getting all this criticism and feedback from the movie industry.”

The 1999 romantic comedy, an adaptation of Shakespeare’s The Taming of the Shrew, saw Stiles share the screen with some of young Hollywood’s finest stars, including Joseph Gordon-Levitt, Larisa Oleynik, Gabrielle Union and, of course, her onscreen flame, Heath Ledger, a seasoned Australian actor who had nabbed his first lead role in an American film.

“A lot of it was negative,” Stiles recalled of the criticism early in her career. “A lot of it was like, ‘You’re too serious,’ ‘You [need to] lighten up.’ You know, trying to be more appealing sexually, whatever. That can be really disheartening, especially as a teenager. So when I read 10 Things I Hate About You, Kat was so refreshing because I loved how unapologetic she was.”

Kat Stratford has a biting tongue and an anarchist vibe. She’s got riot grrrl sensibilities — which would make sense, given the subculture’s start in Washington and her Pacific Northwest roots — and has zero intention of placating the status quo. Speaking her mind is non-negotiable, and popularity contests nauseate her. She’d rather dance her heart out at a Letters to Cleo show than clamor for the attention of narcissistic teenage boys like Joey “Eat Me” Donner (played by Andrew Keegan). Stratford isn’t afraid to let the world know she’s angry.

“I’m totally appreciative of the fact that that movie still means something to people,” Stiles said. “To know that other people respond to that movie the same way that I did is really nice.”

Like many fans of the film, there are a few scenes that live rent-free in Stiles’s mind.

“The stadium scene is pretty memorable for me because I was like, ‘What? Heath Ledger? You can sing and dance and all that?’” she said. “And the scene where I read the poem, actually, because it was really surprising to me. I wasn’t intending to cry that way, but it happened.”

Nowadays, you can catch Stiles showcasing her talents in front of and behind the camera, as both actor and executive producer. She recently traded in her big sister beginnings for a turn at the younger, messier sister in her latest film, Chosen Family, which comes out Oct. 11.

Starring, written and directed by Austin Powers: The Spy Who Shagged Me actress Heather Graham, Chosen Family revolves around Ann, a Rhode Island yoga instructor who, between her all-consuming family and unconventional romantic relationship, struggles to put herself first. Stiles plays Ann’s younger sister Clio, who is fresh out of rehab when the film begins. She is directionless, naive and seemingly incapable of turning her life around. (Stiles describes her as a “grown-up toddler.”)

Clio differs considerably from Stratford.

“[Clio] felt like an opportunity for me to let out all the things that we’re not really allowed to do or say in real life. There are aspects of Clio that are pretty ridiculous and kind of irredeemable,” she said. “But at the same time, I feel like because it’s through a comedic lens her brattiness was something that was really fun for me.”

In the romantic comedy, Clio develops her own kind of organized exercise called “Punchilates,” a hybrid of pilates and, well, punching things. While Ann has dedicated her life to yoga with minimal recognition from her family, Clio’s idea is immediately praised.

“She’s kind of stealing her sister’s thunder,” Stiles said. “Clio’s a hot mess but she’s unapologetic about being a hot mess. She’s not going to hide it. I usually play the more high-functioning person. This was refreshing for me to play the one who’s still living in her parents’ garage.”

Offscreen, Stiles and Graham’s relationship is anything but volatile. In fact, the Silver Linings Playbook actress was immediately drawn to the project after first reading Graham’s script a few years ago.

“I think I’d met Heather once or twice before, but I didn’t really know her personally,” she said. “I just thought she wrote a really great script. The characters were so vivid and clear.”

Stiles soon joined as an executive producer, a move that Graham said ultimately got the film financed.

“I was really fortunate to be able to see [Graham] direct on her own set right before I went into directing my own movie,” she said.

Earlier this year, Stiles wrapped production on Wish You Were Here, a romantic drama adapted from Renee Carlino’s novel of the same name. She also co-wrote the film, which will mark her directorial debut.

As for watching Graham wrap her own film, Stiles said “It was inspiring for me to see her get her movie finished against all odds because it’s really hard to get independent films made these days. I [wanted] to support her and stick with it. I think we just have to lift each other up.”

Chosen Family is in theaters and on demand Friday, Oct. 11.