Posted by Blake Wilde @blakethatblake
High School student. Terrifically awkward | Editor at Some Trend | Twitter: @blakethatblake
Blake Wilde

Warning: Spoilers for Gia, Girl, Interrupted, and George Wallace below.

There's no discussion about Angelina Jolie being one of the most iconic movie starts of this generation. Her career begun in the early '90s appearing in a few of her brother's student films (he went to USC School of Cinematic Arts) and a few music videos. Jolie's first leading role was on Cyborg 2 (1993), which got her really disappointed. But her critic breakthrough only happened later in that same decade. The humanitarian actress is also known by a couple of other major Hollywood productions like Tomb Raider, Mr. and Mrs. Smith, and Salt.

1. Gia

  • Age: 23
  • Year: 1998

I know what you might be thinking, you thought you'd see Girl, Interrupted ranked over Gia. The truth is that HBO's biographical movie about the first America's supermodel, Gia Carangi (1960–1986), was never a highlight to the mass' eyes, on the other hand it received critics high rates. In this movie, Jolie plays a bisexual living on the top of the beauty industry who through persistent loneliness is driven to addiction of drugs.

The big deal about Gia is that it shows both sides of the supermodel who died of AIDS — a disease she probably contracted by the share of needles — in 1986. By that time, much about the subject was unknown and people used to think it was too dangerous to stay close to people with this disease, a myth that made her father chose to stay far from her. Another interesting point is the cruel realistic perspective of the drug addicts.

On screen, Jolie simply gives her all to bring Gia Carangi as it was — the sex, the drugs, the recklessness and all the pain — in a story with high thrills.

Apart from Angelia, Gia brings amazing performances from Mila Kunis (portraying Gia in her childhood), Faye Dunaway (as Wilhelmina Cooper), and Mercedes Ruhel (as Kathleen Carangi).

"Life and death, energy and peace. If I stop today it was still worth it. Even the terrible mistakes that I made and would have unmade if I could. The pains that have burned me and scarred my soul, it was worth it, for having been allowed to walk where I've walked, which was to hell on earth, heaven on earth, back again, into, under, far in between, through it, in it, and above." — Gia Marie Carangi

2. Girl, Interrupted

  • Age: 24
  • Year: 1999

Just a year after Gia, Jolie's performance in Girl, Interrupted (based on Susanna Kaysen's memoir of the same name) received much praise from the critics even though the movie received mixed reviews. Her role on the film won her three major awards: Best Supporting Actress at the Academy Awards and at the Golden Globe Awards, and Outstanding Supporting Female Actor at the Screen Actors Guild Award.

In Girl, Interrupted, Jolie plays a sociopath named Lisa Rowe. "She is charismatic, manipulative, rebellious and abusive. Over her eight years at the [psychiatric] institute she has escaped several times, but is always caught and is brought back eventually. She is looked up to by the other patients in the ward."

The movie also features Winona Ryder (Stranger Things), Brittany Murphy (Clueless), and Whoopi Goldberg.

Some advice: Don't point your f*cking finger at crazy people. — Lisa Rowe

3. George Wallace

  • Age: 22
  • Year: 1997

When George Wallace was released in 1997, that's when Jolie really took a further step on her career. Just like Gia, it was a television movie that won her a Golden Globe Award for Best Supporting Actress – Series, Miniseries or Television Film and an Emmy Award nomination for Outstanding Supporting Actress – Miniseries or Movie.

In George Wallace, Jolie portrays Cornelia Wallace, the First Lady of Alabama from 1971–1978 and the second wife of Democratic Governor George C. Wallace.

The movie also includes Gary Sinise and Mare Winningham.

Check out how much Angelina have changed over the years in this surreal face melt video below:

Now, why don't you tell me about your favorite movies featuring Angelina Jolie? I surely would like to know!