The co-star that left Winona Ryder feeling “intimidated” on set

Since the very start of her career, Winona Ryder has worked with the best. Only two years after her feature debut, the actor was already ticking off a list of the greats, not only starring in their pictures but solidifying herself as a go-to star that they would call up repeatedly. However, there was one name that intimidated Ryder as she found one co-star to be a terrifying castmate.

Very few people can brag that the third film they ever starred in saw them take on a lead role in a Tim Burton flick. After her cinematic debut in 1986 in Lucas, it was only two years later in 1988 that Ryder stepped up to the leading lady plate at Lydia Deetz in Beetlejuice. It was her first of many career-defining role, instantly putting her on a rocket ride to the A-list as her talent in that movie made her one of Hollywood’s most sought after young stars.

From then on, her filmography is a golden run seeing her working alongside other a-list peers as well as being specifically selected by the great directors of cinema history. In 1992, she starred in Francis Ford Coppola’s Bram Stoker’s Dracula. The year after, Martin Scorsese called her up for Age Of Innocence. Spike Jonze cast her in Being John Malkovich, and even Al Pacino wanted Ryder involved when he made his odd directorial debut with Looking for Richard.

But out of all those big names, the one person that truly intimidated the actor should have been a peer. Coming up around the same time, Angelina Jolie was another one of Hollywood’s newest obsessions. However, until the late 1990s, her filmography was notably less high-brow than Ryder’s, instead seeing her be cast as either the love interest or the dark, mysterious heroine, both undeniably cashing in on Jolie’s modelesque good looks.

But in 1999, Jolie was cast as the lead in a decidedly darker and more dramatic film, seeing her step into the spotlight for a role that would forever endure as one of her finest moments. Both Jolie and Ryder were locked in to star together in Girl, Interrupted, a moody flick about mental illness.

On paper, the two stars should have hit it off. They’re relatively the same age, with Ryder being a few years older. Both were relatively new, young stars navigating the world of Hollywood at the start of their careers. However, the friendship that could have bloomed simply never happened.

For Ryder, that relationship was sacrificed for the good of the movie. She said, “I remember thinking, ‘Oh, we’re going to turn out to be great friends,’ but I think she needed to be able to look at me just as the character Susanna, not as Winona, so in a very respectful way she just kind of kept her distance.” As the relationship between their two characters is so complex and toxic, it seemed as though Jolie needed to keep a level of space between the two actors in order to get there with her character.

However, according to others on the set, Ryder’s struggle to break through with Jolie wasn’t uncommon. Elizabeth Moss, who also starred in the film, described a certain atmosphere on set. “There was the Winona Ryder camp and the Angelina Jolie camp,” she said, explaining how the plot of the film seemed to seep into life on set. She added, “Off camera, but based on what was on camera, based on the script. I was in the Winona Ryder camp. The Angelina Jolie camp was really cool. I was intimidated by the Angelina Jolie camp. I had no thoughts of ever being able to be in that camp.”

Perhaps the key difference that kept the two actors apart was their origins. Ryder came from Minnesota and was born to a relatively normal family. Relatively is the only word here as her godfather was the fame countercultural figure Timothy Leary and she was family friends with the likes of Allen Ginsberg. However, those connections can’t hold a candle to Jolie’s as she was well and truly raised to be a star.

Jolie is the daughter of actors Jon Voight and Marcheline Bertrand, so she was brought up in Hollywood. She knew everyone and everyone knew her, so Moss’ intimidation by the “Angelina Jolie camp” was likely a sense of inferiority felt by herself and by Ryder as Jolie moved through the set, and Hollywood on a whole, with a sense of ease and belonging.

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