Sarah Michelle Gellar Almost Starred Opposite Leonardo DiCaprio in This 1990s Love Story

Leonardo DiCaprio has led a legendary Hollywood career. But before he became one of the industry’s most acclaimed and bankable actors, he endured an uncomfortable teen idol phase. This particularly took hold after Titanic was released to record-breaking box office and awards wins. Just before that, DiCaprio nearly worked with a rising star named Sarah Michelle Gellar. Here’s the project that almost put these two actors together.

Sarah Michelle Gellar wears black and poses on the red carpet
Sarah Michelle Gellar | Matt Winkelmeyer

Sarah Michelle Gellar had barely any movie experience early on

These days, Gellar is best known for the title role on the landmark TV series Buffy the Vampire Slayer. However, before that, she earned a Daytime Emmy Award for her role as Kendall Hart on All My Children. In fact, much of the actor’s work was firmly on the small screen. She made a couple of guest appearances on his shows and played Jacqueline Kennedy Onassis in a 1991 TV miniseries. But her movie experience was nearly non-existent.

In fact, prior to Buffy the Vampire Slayer, most of her efforts to break into film were nixed before they even started. For example, Gellar nearly appeared in 1995’s Clueless and a variety of other films destined for greatness. Her biggest movie role up to that point was a supporting turn in the 1989 thriller High Stakes starring Sally Kirkland. But one of the most intriguing what-ifs was that time Gellar nearly landed a leading role opposite DiCaprio.

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The actor almost had a major role before ‘Buffy the Vampire Slayer’

The project in question was William Shakespeare’s Romeo + Juliet. This 1996 adaptation served as a modern update to the classic tale, while keeping the original Shakespearean language intact. And according to Vulture, Gellar was one of many actors who tried to win the role of Juliet Capulet. Jennifer Love Hewitt, singer Aaliyah, Kate Winslet, Christina Ricci, and Natalie Portman — who was deemed too young — all tried for Romeo + Juliet.

Claire Danes ultimately won the role, according to Grazia magazine, because she made eye contact with DiCaprio during her audition. As for Gellar, she would co-star with Hewitt in I Know What You Did Last Summer the next year. That movie hit theaters just seven months after Buffy the Vampire Slayer debuted. And it kicked Gellar’s film career into full gear. Over the years, she’d appear in hits such as Scream 2, Cruel Intentions, Scooby-Doo, and The Grudge.

Sarah Michelle Gellar currently plays another fan-favorite character

In recent years, Gellar’s acting career hasn’t been as much of a priority. After all, she has other business interests and a family with frequent co-star and husband Freddie Prinze Jr. But even so, Gellar has dabbled in television work in the past decade. Following the short-lived sitcom The Crazy Ones opposite Robin Williams, Gellar joined Prinze on Star Wars Rebels for a few episodes.

And her latest role continues Gellar’s voice work. In 2021, she voiced Teela in the Netflix animated series Masters of the Universe: Revelation. The show divided fans with its increased focus on Teela. Nevertheless, the show earned strong reviews overall. Thus far, 10 episodes have hit the streaming service.

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