In 2016, Olivia DeJonge got her first ever major role in a TV series. She was cast as the main female lead in the pilot for the TNT miniseries "Will," a fictionalized account of Shakespeare's life aimed at Gen Z, per Deadline.

The part would prove challenging for the actor since she had zero interest in Shakespeare and always struggled to engage with his works at school. Thus, she almost turned down the offer. "Before I read the script, I wasn't interested, because I didn't like Shakespeare. At all," she told Nylon. "Thought he was boring and dusty." Once the writers explained the premise to her, she hopped on board. "If it could change my opinion on Shakespeare, it could probably change anyone's," she added, noting that prior to the writers' modernization of the language, Shakespeare's lingo had always left her confused.

But "Will," which Variety describes as a punk rock interpretation of the Bard, intrigued DeJonge, who was drawn to the themes of rebellion. "The guys had amazing leather jeans, which I also wanted," she said. "I always had a funky belt, or a funky leather jacket. So much detail went into the costumes." Starring alongside Laurie Davidson, who played the titular playwright, DeJonge portrayed Alice Burbage, a progressively minded love interest who gives Will a run for his money, per The Hollywood Reporter. In a mixed review, IndieWire pinpointed DeJonge's performance, declaring that she had a "star quality presence" and praising her character's infusion of feminism into the plot.

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