Julia Stiles Was ‘Starstruck’ Auditioning Against Natalie Portman in the '90s: 'She Was Way Famous Already'

Julia Stiles crossed paths with many other famous actresses in the '90s, but one encounter still stands out to her.

“I do remember seeing Natalie Portman and being really starstruck and thinking, ‘Oh, I’m never going to get this job,' " the Wish You Were Here director told PEOPLE during an episode of the PEOPLE in the ‘90s podcast in 2021. “She was way famous already.”

At the time, Stiles, now 43, was a teenage actress auditioning for roles in New York City. The 18-year-old was living with her parents in 1999, the same year she appeared on the cover of Teen PEOPLE as one of the '21 Hottest Stars Under 21.' She was named alongside other '90s icons like Justin Timberlake, Joshua Jackson and Katie Holmes.

“I was auditioning in New York, which is kind of a smaller group,” the Jason Bourne actress said. "LeAnn Rimes, Josh Hartnett and Michelle Williams, they were probably all in L.A.," she added of some of the other stars on the Teen PEOPLE list with her.

But Stiles rubbed elbows with her fair share of future megastars on the East Coast, too. 

“My last year of high school, I switched to a performing arts school and Christina Ricci was there,” Stiles recalled.

The budding actress’ circle of famous friends grew as she continued to work and book roles.

“Once you actually have the job and you’re on location, not only are you sort of forced to hang out with everybody and you quickly become friends, but you have the confidence of, I’ve already got the job,” she says. “People that you would see every day, we’d become more friendly with.”

In more recent years, the mother of three has taken a step back from acting but still appears in projects from time to time. In 2024, she starred alongside Heather Graham in Chosen Family. This year, she is making a foray into directing. 

Related: Julia Stiles Was 'So Happy' Son Saw Her in a 'Leadership Role' on Wish You Were Here Set: 'He Didn’t Want to Leave' (Exclusive)

PEOPLE recently caught up with the star at the premiere of her directorial debut, Wish You Were Here, on Jan. 15 in New York City, where she reflected on her character Kat Stratford in 10 Things I Hate About You, the role she gets “recognized” for most.

“I was a 17-year-old actress auditioning and getting a lot of annoying comments like, ‘You're too serious,’ or ‘You need to be sexier,’ or ‘Smile more,’ and I was vulnerable to it because I was still trying to figure out who I was," Stiles said.

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"And then I read 10 Things I Hate About You and Kat Stratford was like this feisty outspoken girl who did not care what people thought about her,” Stiles continued of the character, who played opposite the late Heath Ledger’s Patrick Verona.

“So it meant a lot to me to be in that movie," she said, "and that it resonates with people still is so great.”

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