Brad Pitt: The Women Who Shaped The Hollywood Legend

Just like climbing to the top of Hollywood, Brad Pitt’s personal life was full of challenges. And unfortunately, it has not been as successful as his acting career. We dug up some details of Brad's dating history, and let us assure you, there some intriguing and shocking facts. Learn how his love life and his career path developed over the years.  

Brad Pitt's journey to stardom wasn't an easy one / Getty Images

Brad Pitt's journey to stardom wasn't an easy one / Getty Images


GWYNETH PALTROW

Gwyneth is the woman it all started with for Brad. Well... Not really with her. It’s no surprise that Brad Pitt dated A LOT OF WOMEN in his twenties. So many that Ellen DeGeneres once found out that she dated the same woman Pitt did! Or even two of them... But Gwyneth Paltrow was the first super-famous celeb on Brad Pitt’s list.

Getty Images

Getty Images


And no doubt she was the first one who increased Pitt’s value as a man. Pitt met Paltrow on the set of the hit movie Seven in 1995 and they immediately fell in love with each other. Things also started to go well in his acting career and Brad felt like he was ready for the next serious step in their relationship.

Brad Pitt and Gwyneth Paltrow attend the 1996 Golden Globe Awards / Getty Images

Brad Pitt and Gwyneth Paltrow attend the 1996 Golden Globe Awards / Getty Images


He proposed to Gwyneth. And the actress agreed (as if any lady could possibly say “no” to Brad Pitt...). It seemed like nothing could separate the lovely couple. Even Harvey Weinstein. Yes, there was that thrilling story when the tyrannical producer sexually harassed Paltrow and Pitt dared to confront Weinstein, knowing that both he and Paltrow could lose their careers because of it.

"At that moment, I was just a boy from the Ozarks on the playground," Pitt explained to Christine Amanpour later, "and that's how we confronted with things."

Brad Pitt stood up for Gwyneth Paltrow when she was being harrassed by a producer / Getty Images

Brad Pitt stood up for Gwyneth Paltrow when she was being harrassed by a producer / Getty Images


But unfortunately, the lovely couple later split in 1997... And nobody knows exactly what went wrong. Although Paltrow has always taken responsibility for their break up, saying:

“I was such a kid, I was 22 when we met,” Paltrow told Howard Stern. “You can’t make that decision when you’re 22 years old… I wasn’t ready, and he was too good for me.”

Talking about Brad Pitt, he never seriously commented on their split. It seemed like he was ready for someone bigger, though. He was ready for...

Brad Pitt and Gwyneth Paltrow unfortunately split up for unknown reasons / Getty Images

Brad Pitt and Gwyneth Paltrow unfortunately split up for unknown reasons / Getty Images


JENNIFER ANISTON

You might know part of this story. But you definitely don’t know the whole story. 7 years of a happy together life and all of a sudden one of the most beautiful couples in Hollywood breaks up... So what happened? What made Jennifer Aniston say “there’s a sensitivity chip missing" in Pitt?

Jennifer Aniston and Brad Pitt used to be one of the most beautiful couples in Hollywood / Getty Images

Jennifer Aniston and Brad Pitt used to be one of the most beautiful couples in Hollywood / Getty Images


They first met in 1994. Their managers were actually friends and introduced them to each other. But everything only started a few years later, after Pitt broke up with Paltrow. Pitt and Aniston met again in 1998 and all of a sudden a bright, powerful spark occurred, which led to a long-term relationship that grew into something truly beautiful.

Again, you can’t tell much about their relationship with Pitt. Because, you know, the legendary actor doesn’t like to talk much about that kind of stuff. But Aniston does! Many of their fans know that it was none other than Angelina Jolie who stepped in and changed everything for the married couple.

Jennifer Aniston revealed it was awful for her after her break-up with Brad Pitt / Getty Images

Jennifer Aniston revealed it was awful for her after her break-up with Brad Pitt / Getty Images


But not many know how awful things were for Aniston afterwards... We’ll talk a bit later about why Pitt chose Jolie over Aniston and about their relationship and divorce, but for now let’s speak about what happened soon after Pitt and Aniston divorced in 2005. Just a few months later The W magazine posted that cruel set of photos...

The pictures showed Pitt and Jolie as a lovely family from the 60s with lots of kids. The series was called “Domestic Bliss” and taking the timing into account, you can understand why it hurt Jennifer Aniston so much.

“Brad is not mean-spirited; he would never intentionally try to rub something in my face.”

Aniston always protected her ex-husband in the media / Getty Images

Aniston always protected her ex-husband in the media / Getty Images


Aniston protected her ex-husband in her talk with Vanity Fair. “Brad would say, ‘That’s art!”... But there’s a sensitivity chip that’s missing.” Pitt and Aniston didn’t want to set any hate in public. They decided to make their official statement to PEOPLE, saying that after seven years together they had decided to formally separate.

For those who follow these sorts of things, they would like to explain that the separation is not the result of any of the speculation reported by the tabloid media. As tragic as it was, Pitt and Aniston’s love story had ended.

And it led to several things. Bad things, like depression. And very bad things, like addictions. Though there was a good thing too! Something that lived long after their divorce... Their mutual production company, that is called:

Aniston and Pitt divorced in 2005 / Getty Images

Aniston and Pitt divorced in 2005 / Getty Images


PLAN B ENTERTAINMENT

And because of it, the world has seen lots of great cinema, such as World War Z, 12 Years a Slave, The King and, of course, Ad Astra. Pitt’s production company really put him on a serious level not just as an actor but as a Hollywood figure. Cause without it Brad Pitt might never have become a cinema legend. 

Brad Pitt launched a production company called Plan B Entertainment / Getty Images

Brad Pitt launched a production company called Plan B Entertainment / Getty Images


Could we call him a terrific actor without Plan B? Of course. A sex symbol? For sure! He was named “Sexiest Man Alive” by People magazine twice! In 1995 and 2000. But being able not only to act but to produce serious cinema made him who he is today... 

And as tragic as it is, you can’t become a Hollywood living legend without paying a price, and his price was tough. At the time of his biggest success, Brad Pitt suffered from addictions and long-term depression...

Brad Pitt was twice named the sexiest man alive / Getty Images

Brad Pitt was twice named the sexiest man alive / Getty Images


YEARS OF UNEASE

It’s almost impossible to believe but at the end of the 90s, Pitt became really sick of himself. It’s way too complicated to understand. Even for Pitt. Because, come on! Just look at the list of movies he made at the end of the 90s and beginning of the 2000s: Seven, 12 Monkeys, Fight Club, Snatch!

Brad Pitt couldn't always bear the pressure of fame / Getty Images

Brad Pitt couldn't always bear the pressure of fame / Getty Images


What could be depressing about that? Probably, this is the kind of depression only insanely famous people can get. Like Daniel Radcliffe, for example, who couldn't face his huge popularity after Harry Potter and turned to drinking... Pitt told Hollywood Reporter that he was hiding from the celebrity thing that dropped on him insanely at that period of time.

Or perhaps, he didn't admit the true reason behind his depression? Could be. Pitt confessed that he was smoking way too much dope.

“I was sitting on the couch and just turning into a doughnut; and I really got irritated with myself," he said. "I got to: 'What's the point? I know better than this."

Pitt suffered from many problems over the course of his career / Getty Images

Pitt suffered from many problems over the course of his career / Getty Images


But it seemed like nothing could help him then. Pitt faced true depression. He started drinking.  And of course, that only increased the feeling of unease he had. At some point, Pitt confessed to himself: “This is a waste”. So what saved him? Seeing people who were in much worse situations than he was in.

Yes, at the end of the 90s he went on a trip to Casablanca, where he saw poverty to an extreme that he had never witnessed before. All of a sudden he understood that his depression was nothing compared to what poor people were facing there.

“It stuck with me. I just quit. I stopped grass then -- I mean, pretty much -- and decided to get off the couch."

After that, he started a new life. And that is one of the reasons why he became so close with another Hollywood celebrity with a huge and kind heart. With...

Brad Pitt found his way out of problems and started a new life / Getty Images

Brad Pitt found his way out of problems and started a new life / Getty Images


ANGELINA JOLIE

This is the longest and most serious relationship Pitt has ever had so far. They raised 6 kids together and were together on a challenging journey for 12 years. Wait a second... Did that inspire Pitt’s movie “12 Years a Slave”? Okay, just kidding. So how did things start for Brangelina?

Brad's relationship with Angelina Jolie has been the longest one he's had so far / Getty Images

Brad's relationship with Angelina Jolie has been the longest one he's had so far / Getty Images


As many fans know they first met on the set of Mr. and Mrs. Smith in 2005. Despite the fact that Pitt and Jolie initially denied it, they later confessed that they immediately fell in love with each other while doing this movie. The biggest problem here was... that Pitt was still married to Aniston at the time.

But you know how the story goes from here. Everybody in the world knows it! Pitt chose Jolie over poor, heartbroken Aniston, and in 2012 he proposed to Angelina, giving her a $1 million dollar engagement ring! Two years later they were married in France, and all of their 6 kids were involved in the ceremony.

Brad and Angie raised six children together / Getty Images

Brad and Angie raised six children together / Getty Images


Yes, they had kids before they got married... But what was so special about Jolie that made Pitt do all of that? We have a guess. Brad Pitt’s unbelievably long path to success, which was full of hard challenges, and that brought him unbelievable wealth, showed him one thing: he wanted to share what he received during his life with those who needed it.

And Jolie felt the same. You’ve probably heard that Brangelina did a lot of charity work. But according to one of their close friends who noted anonymously to Hollywood Reporter:

"You have no idea how much money they give away. It's millions and millions and most people never even hear about it."

Brad and Angelina revealed they fell in love with each other while filming Mr. and Mrs. Smith / Getty Images

Brad and Angelina revealed they fell in love with each other while filming Mr. and Mrs. Smith / Getty Images


Their relationship was more than about each other. More than about their kids. It was truly universal. But for some reason fortune hasn't smiled on Brad Pitt when it comes to his relationship with women. And one of the world’s most iconic couple ended their relationship in 2019...

“For me this period has been about looking at my weaknesses and failures and owning my side of the street.” Pitt described to GQ style.

Brad and Angie's relationship was truly universal / Getty Images

Brad and Angie's relationship was truly universal / Getty Images


He was very close to starting drinking again. But he was a much stronger person this time around. When asked how he quit drinking, Pitt answered that he didn't want to live that way anymore. So he's sober now. But why did Brangelina break up? The official statement was made by Jolie:

"I separated for the well-being of my family," she told Vogue India: "It was the right decision."

And that was it. Nobody knows the truth. Except for Brangelina themselves.

Nobody knows for sure why Brangelina broke up / Getty Images

Nobody knows for sure why Brangelina broke up / Getty Images


BRAD PITT TODAY

Despite the fact that fans can't stop imagining Jennifer Aniston and Brad Pitt being together again, none of this speculation has any truth behind it. Yes, even despite the fact that Aniston invited Pitt to her 50th B-day! Sorry... But we'll definitely keep an eye on these two, don't worry.

Brad Pitt might be making up with his ex Jennifer Aniston / Getty Images

Brad Pitt might be making up with his ex Jennifer Aniston / Getty Images


What we really appreciate about Pitt is his self-irony. In case you missed his amazing speech at the 2020 SAG Awards we’ll do a small recap for you. As he accepted his award for Best Supporting Actor for “Once Upon A Time... in Hollywood” he didn’t hesitate to make fun of himself while on stage!

"Let's be honest, it was a difficult part. A guy who gets high, takes his shirt off, and doesn't get on with his wife. It was a big stretch."

Brad Pitt and Jennifer Aniston at the 26th Annual Screen Actors Guild Awards on January 19, 2020 / Getty Images

Brad Pitt and Jennifer Aniston at the 26th Annual Screen Actors Guild Awards on January 19, 2020 / Getty Images


He also joked that he’s gonna add his new achievement to his Tinder account! And here’s more for you: when he appeared on the WTF with Marc Maron podcast he trolled himself over his “disaster of a personal life”. So here’s our take-away from Brad's long and difficult story: If you've had several marriages and none of them were successful at least have the courage to laugh at yourself.

We love Brad Pitt for his incredible self-irony / Getty Images

We love Brad Pitt for his incredible self-irony / Getty Images


MORE SUCCESSFUL AREA

Luckily, Brad's career has been much more successful than his love life, although, it wasn't an easy path either. Brad Pitt was absolutely nobody in the late 80s - it seemed like the only thing he had was his dream of becoming an actor. That’s why he took a chance and left university just 2 weeks before earning his Journalism degree and moved to LA with only $325 in his pocket!

Brad Pitt has always dreamt of becoming an actor / Getty Images

Brad Pitt has always dreamt of becoming an actor / Getty Images


Do you think Lady Luck smiled down on Pitt? Not at all. He had a number of weird jobs before appearing on the screen. For example, in the 80s Brad Pitt worked in LA as an El Pollo Loco mascot. Yes, the future actor had to wear a yellow chicken costume and invited pedestrians to visit the fast-food restaurant. Crazy, right?

In the 80s Brad Pitt worked in LA as an El Pollo Loco mascot / Getty Images

In the 80s Brad Pitt worked in LA as an El Pollo Loco mascot / Getty Images


But Pitt has absolutely no shame about it. “Man’s gotta eat” he explained to Ellen DeGeneres on her show. Another weird job Pitt had was driving a limo with exotic dancers! Believe it or not, but this job was kind of life-changing for the young actor. According to his interview for People, Pitt once drove a stripper who attended acting classes of the legendary teacher named Roy London.

The stripper recommended that Brad visit his classes, saying that Roy London was one of the best coaches in Hollywood. So Pitt did, and that’s what set him on the path to where he is now. “Strippers changed my life,” Pitt loves to joke. We are definitely glad his dream of becoming an actor has come true!

In 2020 Brad won his first Oscar / Getty Images

In 2020 Brad won his first Oscar / Getty Images

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