How did Angelina Jolie look in her prime as a global icon?

When you see Angelina Jolie in an oversized sweater, curled up on a chair, hair wind-swept, with a coy cat-like smile, it’s hard not to think, This is a woman who doesn’t have a care in the world.

Her reality is the opposite of a lazy day at the beach. She’s a mother of six, movie director, movie star, UN ambassador, humanitarian, and global citizen.

Right now she’s filming two new Disney movies: Maleficient 2 and The One and Only Ivan.

Yet it can be argued that the most interesting aspect of this incredible celebrity is the evolution of her character and the transcendence of her physical beauty by her deep emotional life.

To date, Jolie has received an Oscar, two SAG awards, and three Golden Globes, and has received ten nominations for film and television roles. Jolie first rattled Hollywood in the HBO film Gia.

Her role as a troubled model with self-destructive tendencies and heavy drug use was a far cry from the mainstream fairy tale movies of the ’90s.

Although she was initially worried that HBO would try to tease out a pretty story from Gia’s experience, Angelina moved forward with the role. The filming ended up being a harrowing experience for Jolie and the emotional toll of becoming Gia moved her to briefly study screenwriting to clear her head.

At this point, she was just a fledgling star, but the industry took note of her impactful beauty and the roles started to pour in. She quickly filmed Playing by Heart, Pushing Tin, and The Bone Collector opposite Denzel Washington. Although she had chosen the edgy role of Gia in order to be taken as a serious actress, it seemed that her beauty catapulted her quickly into mainstream roles.

A year after Gia, Angelina Jolie came back to the big screen in a major way. She starred in Girl, Interrupted and this time she made waves in Hollywood both on camera and off.

The movie was supposed to have been an Oscar vehicle for Winona Ryder, who was the film’s lead actress and executive producer. Winona fought for Jolie, a relatively unknown actress at the time, to be a part of the film. Later, when Jolie won an Oscar for her role as Lisa Rowe in the film, the tabloids exploded with rumors of Winona’s disappointment over not being thanked for the opportunity she gave Jolie. But even more explosive was Jolie’s edgy behavior at the 2000 Oscars.

Her dress and long black hair were reminiscent of Morticia Addams, and a kiss on the lips with her brother, James Haven, seemed to linger too long for anyone’s comfort. That kiss was a repeat of one photographed at the Golden Globes three months earlier. After that moment, it seemed like a string of strange publicity from wearing matching blood vials with her then husband, Billy Bob Thornton, to very bluntly discussing extreme behaviors of her youth as often as possible.

In an interview with Vanity Fair, Jolie said, “I actually feel more of a woman because I feel like I’m being smart about my choices, and I’m putting my family first, and I’m in charge of my life and my health. I think that’s what makes a woman complete.” Jolie said what keeps her up at night is thinking, “Did I do a great job as a mom or was that an average day? I’ve been trying for nine months to be really good at just being a homemaker and picking up dog poop and cleaning dishes and reading bedtime stories… And I’m getting better at all three.”

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