When it comes to famous actor heartthrobs, there’s no denying that Brad Pitt is near the top of the list, no matter who you ask – and he’s been there for some three decades at this point.
Still, as a winner of two Academy Awards – one for producing 2013’s Twelve Years a Slave, the other for his career-best supporting performance in 2019’s Once Upon a Time… in Hollywood – Pitt has in recent years become known for far more than just his pretty face. Today, with some 60 producing credits to his name, and with many of those projects critically acclaimed, Pitt’s a Hollywood power player reminiscent of the likes of Kirk Douglas and Burt Lancaster.
Having starred in everything from glossy romantic comedies, to gritty dramas, to historical fiction, Pitt has had one hell of a varied career. We’re taking a look back at his beginnings, as well as some of the things you still might not know about Brad Pitt.
25. He went to extremes to make himself uglier in Fight Club
There’s no denying that Brad Pitt has always been a Hollywood heartthrob, especially in the late nineties and the early 2000s.
However, for one particular role, he had to abandon the handsome boy next door persona for something way grittier.
For Fight Club, Pitt got into the rough and tumble spirit of the role by going to the dentists to have his teeth professionally chipped.
The thinking was that despite the character’s good looks, he wouldn’t have escaped unscathed after months of leading Fight Club.
With the chip, he looked like he’d been in exponentially more fights than he actually had, even if he immediately got his teeth fixed after shooting.
24. He had a serious co-star crush
When Brad Pitt first signed on to star in the steamy spy movie Mr and Mrs Smith, Nicole Kidman was set to star alongside him.
However, their lack of chemistry was obvious after just a few rehearsals together, which led Pitt to voluntarily drop out of the project.
When producers cast Angelina Jolie instead however, Pitt immediately signed back on, wanting to get to know her more.
It’s obvious that the two of them were not short on chemistry, as soon after the movie the two got engaged in real-life.
With that said, Pitt probably didn’t know he was shooting with his future wife the first time they were on set together.
23. He tore his Achilles tendon playing Achilles on the set of Troy
Brad Pitt’s irresistibility as a leading man has led to him being cast in all sorts of things, from romantic comedies, to dramas.
It even led him to take on historical pieces like Troy, which many other contemporary leading men in Hollywood have traditionally distanced from.
In Troy, Pitt played a famous mythical character called Achilles, which soon came back to haunt him.
During production, Pitt literally tore his Achilles, a serious injury that put him out of comission on set for a little while.
The injury is the same one his character is literally famous for dealing with and even inspiring the name of, talk about getting into character.
22. His management team wouldn’t let him do American Psycho
Despite the many diverse roles Pitt has been allowed to play in his time, some of his dream ones just weren’t meant to be.
For example, he was scouted and heavily pushed towards the role of Patrick Bateman, but his agent wasn’t willing to let him pursue the part.
His whole team were worried that his fanbase of mostly young women, wouldn’t take kindly to him being in a movie as violent and nihilistic as American Pyscho.
As a result of their wariness, the role ended up going to Christian Bale.
It’s a good job the casting eventually went that way, because Bale’s performance went on to become iconic, and even influence the kind of roles he was offered in the future.
21. His looks got him banned from TV in Malaysia
As well as numerous film appearances, Brad Pitt has also done his fair share of commercials, lending his recognisable face to the promotion efforts of a bunch of different products and companies.
Most notably though, he did a series of car adverts for Toyota.
These adverts were considered so handsome and irresistible that they were literally banned from airing in parts of Malaysia.
The reason being the government thought men would constantly compare themselves to Pitt in the adverts, and end up feeling inferior about their own looks.
That’s pretty unprecedented, and kind of makes him the most attractive man in the world, as far as the country is concerned at least.
20. He was kind of a dweeb in school
Nowadays, Brad Pitt is the definition of having it all.
He’s rich, good looking and massively successful in his career, and until recently was married with kids to one of the most famously beautiful women in the world.
That success took a while though, as in his school years he was kind of a dweeb.
Such a dweeb in fact, that he was rejected from his school’s sports team, even after trying out a bunch of times.
In fact, he later started his own team with all the other rejected kids that he then asked his dad to coach.
19. He has a serious dark side
Brad Pitt might have played some dark parts over the years, but everyone knows he’s definitely more of a good guy in real life.
That’s why it’s so surprising that he bought his house from the Queen of Darkness herself, Elvira. Or, more accurately, the woman who plays Elvira.
Pitt bought her California mansion directly from her, with all of her gothic and horror-themed furniture still inside.
He had to do some serious redecorating to make it a place fit for a family with young children, but the big spider web feature window is still visible.
However, even if he disliked the gothic picture window, it’s probably not that much of an upset to him, given how much other property he owns.
18. …But not enough to get Christian Slater’s role in Heathers
Despite this dark side, Brad Pitt was denied the chance to play one of the darkest characters of the late 80s.
Pitt auditioned to play JD in Heathers, the sociopathic love interest who goes from everyone’s dream boyfriend to everyone’s nightmare within less than a year of school.
Pitt had the acting ability to star in Heathers, and had proved that he had the chops to carry a whole movie by himself.
However, casting directors saw Pitt’s handsome looks and blonde hair, and decided he was just too sweet-looking to play the character.
Christian Slater was cast instead, which is a large part of why the movie has such a cult following.
17. He has literally broken records for sexiness
Even though his looks have occasionally stopped him from getting the edgier roles in Hollywood, his handsomeness has also been a serious asset to him at times.
He actually set a record, by being the first person in the world to be named the sexiest man alive twice by People magazine, winning the award first in 1994 and then again in 2000.
Since then, many other actors have had the honour of winning the award twice: from Johnny Depp to George Clooney, to Richard Gere.
In fact, even some non-actors have since received the award, though not many, with Adam Levine and David Beckham being the exceptions.
Brad Pitt has also won some other awards for sexiness, including sexiest dad and one half of sexiest couple.
16. One of Pitt’s fans once snuck into his house and tried his clothes on
Being a celebrity is a blessing, but it can also be a curse, and the negative sides of fame tend to intensify the more successful you get.
One of those negative aspects is stalking, which is something Pitt has had to deal with on a number of occasions.
One stalker in particular took things way too far, when she snuck into his house, dressed in his clothes, and sat hiding in his wardrobe for several hours before the alarms gave her away.
As she was only 19, she was determined not to have been a danger, but she did have a restraining order put on her for several years.
Unfortunately, that’s not even the only creepy run in with a fan Pitt has had to deal with, even if it’s by far the most dramatic.
15. He sold fast food dressed as a giant chicken before he became a star
For most aspiring actors, acting is only ever a side job or a hobby, something that brings in a little extra cash but isn’t usually enough to pay the pills.
In fact, even amongst the ones lucky enough to act full time, second jobs to fill the days between shooting and auditions are pretty common.
Brad Pitt is such a starlet, and has been a big name for so long, that it’s unlikely he will ever have to work a normal job again.
However, it wasn’t always the case that he could rely on acting for his income, as he had to work a few seriously odd jobs to make ends meet during his teenage years.
Not only did he work as a limo driver dedicated exclusively to taking strippers from a to b, but he also had to sell fast food while dressed as a giant chicken, and that was when he wasn’t carrying fridges from truck to warehouse.
14. He does extensive charity work all around the world
Many celebrities try to spend their spare time giving back to communities that need it, but very few people take that work more seriously than Brad Pitt.
Pitt is one of the most dedicated charity workers in the acting world right now, flying all over the world to physically help communities that need it.
After being invited by Richard Branson, the CEO of Virgin, he visited hundreds of orphans affected by HIV and other illnesses, and discussing funding for treatment options.
He was also privileged enough to meet Nelson Mandela and discuss his own personal charity, which aimed to combat the problem of an AIDs epidemic in South Africa.
As if that wasn’t enough, he then flew to Ethiopia to work with the charity DATA, which was created by another musician, Bono from U2.
13. He even went on ‘charity dates’ with his wife
Angelina Jolie is maybe the celebrity most famous for their charitable work, so it makes sense that she involved Pitt when the two of them were an item.
In 2005, the two of them travelled to Pakistan to survey the damage of the Kashmir earthquake, trying to discover the best way to deliver aid.
The two also went to Hati, where they visited several schools and children’s centres affected by natural disasters.
There, they lent their money and time to another musician-created charity, this time created by rapper Wyclef Jean.
That’s not to mention, Pitt throwing his support behind Jolie’s United Nations work.
12. He dropped out of college two weeks before graduating
It’s not unusual for superstar actors to have never attended college and university, as they often have been working in the industry from childhood.
However, it’s more unusual for an actor to attend university for a subject completely unrelated to acting, only to then drop out.
That’s exactly what happened for Brad Pitt however, as he got good enough grades to be admitted to university on a journalism course.
He also joined the fraternity of Sigma Chi, and stayed enrolled in the college for the full three years of the degree.
With that said, he dropped out of college to pursue acting just two weeks before graduation and moved to LA with just a few hundred dollars in his pocket.
11. He sued the company that made his engagement ring
Brad Pitt is famous for a lot of things. He’s famous as a heartthrob, he’s famous as a leading man, and he’s famous for his ability to look awesome in car commercials.
However, if he’s famous for one thing aside from all of that, he’s famous for his marriages. Whether it’s to Jennifer Anniston or Angelina Jolie, his relationships aren’t just newsworthy – they’re front-page news.
Though his decision to propose to Jolie definitely caused a stir all of its own, it was his first marriage to Friends’ alumni Jennifer Anniston that ended in a lawsuit.
He hired a jewellers company to design a bespoke engagement ring for him to pop the question to Anniston with, and stipulated specifically that they could never use the design for another client.
So he felt he had no choice but to take them to court when he discovered that, not only were they selling the design openly on their website, but they were selling it under the name ‘Brad and Jennifer’s engagement ring’.
10. He spent time in a real mental hospital to prepare for Twelve Monkeys
For every role Pitt has played that have required him to be a slick a handsome leading man, he’s also played some roles that required him to get seriously gnarly.
Several of his characters, including Tyler Durden in Fight Club fit this bill, but none so much as the character he plays in Twelve Monkeys.
In Twelve Monkeys, Pitt plays a mental patient who is involved with the release and spread of a deadly virus, which wipes out humanity as we know it.
The character is one of the more grounded and dark elements of the film, and required Pitt to research the role by spending the day in a genuine mental hospital.
Pitt spent the whole day on the psychiatric ward, talking to both patients and doctors, which he used to inspire the more exaggerated elements of the character.
9. His children have some pretty unusual names
Celebrities giving their children odd names is so common nowadays that it’s almost become a meme.
Given that Brangelina were one of the most famous celebrity couples in existence in the early 2000s, it makes sense that they’d choose unique names for their children.
The couple have six children together, some adopted and some biological. The eldest biological child is called Shiloh, while the two younger are twins, called Knox and Vivienne.
As for the adopted children, they are called Maddox, Pax and Zahara.
All the children present were involved in the two’s wedding ceremony, helping to write and even perform the vows.
8. He used to be a bit of a playboy
Most A-List celebrities will say in interviews that dating while in the spotlight is impossible, and there’s no denying that it does have its own unique difficulties.
It’s hard to make it through the opening stages of a relationship when dozens of cameramen are there to capture every tiny step, and it doesn’t really get better for those in longer term relationships either.
However, for all the paparazzi and lack of privacy, some people thrive while attempting to date under the watchful eyes of their fans, and one of those people is apparently Brad Pitt.
Pitt has had a whole slew of girlfriends in the time before he got married, and even switched long-term partners, and all with people who you could easily find in any copy of the TV guide.
First he made a stir by dating Julianne Lewis, who was a controversial match because she was a full decade younger than him, and still a teenager when the two began dating.
Then came Gweneth Paltrow, who he was even briefly engaged too, before the two marriages to Angelina Jolie and Jennifer Aniston that both hit the headlines instantly.
7. He owns an unbelievable amount of property
We’ve already discussed how Brad Pitt purchased a gothic mansion from a Hollywood horror legend, which was only one of several properties he owned.
With that said, it’s kind of hard to understand the scale of all the real estate he owns, especially when you look at what he owned whilst married to Angelina Jolie.
For starters, the two owned a shared country mansion in France worth 60 million dollars, which came with over a thousand acres of land.
The two also owned a vineyard in Italy that was worth 41 million, and also came with a whole slew of land.
That’s not to mention the couple’s former homes in both London and New Orleans, which combined are worth more than 20 million dollars.
6. He angered George Clooney by beating him to the role of JD in Thelma & Louise
By the time Brad Pitt won his first serious part, he was already a veteran of the entertainment industry.
He had worked as an extra for an extended period of time in Hollywood, as well as gaining minor parts here and there.
However, his first major role was in Thelma and Louise, a crime thriller / bff road trip movie starring Susan Sarandon and Greena Davis.
The role was of the character of JD, a handsome but sly thief who double-crossed the two friends after initially seeming to be exactly what they needed.
Pitt got the part despite his relative lack of experience in the industry, and it soon proved to be exactly what he needed to gain mainstream recognition and acclaim.
This angered the older leading man George Clooney, who had gone to round after round of auditions for the part and then eventually lost out to someone green and inexperienced.
5. He has a blink and you’ll miss it Friends cameo
There’s a popular joke in entertainment that no matter what you come up with as the plot for your TV episode, chances are it will have already happened in an episode of The Simpson’s.
In recent years, it seems like it’s gotten even more sinister, as a bunch of truly random real-life events have apparently been predicted by the show.
With that said, the real-life TV equivalent seems to be that if you have a favourite actor who was an up and comer in the nineties, chances are they cameo’d in an episode of Friends.
From Bill Murray and Robin Williams to Reece Witherspoon and Susan Sarandon, it’s hard to imagine a mid-level household name, and even a few genuine superstars, who ended up at Central Perk.
Obviously Brad Pitt made an appearance, playing the role of a childhood friend of Ross’ who completely despises Rachel, but he’s not the only one.
In fact, most of his Ocean’s Eight costars, namely George Clooney, Julia Roberts and Ellie Gould, have all also appeared on the show.
4. He seems to have a thing for numbered movies
Every actor has roles or films that they’re drawn to more than others, and they have different reasons for the kinds of roles they find most captivating.
Some have directors they return to time and time again, like Samuel L. Jackson and Quentin Tarantino, while some are prolific for working with a bunch of different people, but always within the same genre.
As it turns out, Brad Pitt’s own movies have a theme, although it makes far less sense than either genre or the people directing. Instead of either of those things, he seems to gravitate towards movies with numbers in.
Not any old numbers either, as his movies tend to either contain a twelve or a seven. In only a few short decades, he has made his way through Twelve Monkeys, Ocean’s Twelve and 12 Years A Slave.
As for the seven side, he’s worked on Sinbad: Legend Of The Seven Seas, Seven Years In Tibet and, most obviously of all, Se7en.
3. The Jackass movies are some of his favourite films
Brad Pitt has done a whole bunch of things in his acting career, from schlocky action flicks, to gooey romantic comedies, to incredibly high brow dramas.
Given that, you could expect his favourite movies to be in any of those genres, or at the very least some kind of highly cinematic work that actors tend to love.
That’s why it’s pretty surprising that his favourite movies are actually the Jackass films – you know, the ones where a group of guys drink each other’s sweat, force each other to get stung by thousands of bees, and just generally put themselves in mortal peril.
Pitt loved the Jackass guys so much that he essentially begged to work with them, and eventually got his wish when he cameo’d on the show in a gorilla suit.
Not only that, but the Jackass guys did another joke where they kidnapped him, though his action movie training meant it probably wasn’t that much of a problem.
2. His rubbish English accent got him a role in Snatch
Maybe the best thing about being a world-class actor is the ability to pick and choose what parts you get to play, whether that’s reading scripts and knowing you’re almost guaranteed a part, or just calling the director directly.
In fact, some actors are so well respected that they can simply get in touch with the director of a film they deeply admire, and straightforwardly ask if they can appear in their next project.
Thats what happened when Brad Pitt saw Lock, Stock and Two Smoking Barrels. He was obsessed with it, and similarly obsessed with the idea of appearing in a movie directed by Guy Ritchie.
Soon enough, Ritchie had a project in the works called Snatch, and immediately called Pitt to confirm that he’d still be interested in appearing.
Pitt was, but when he auditioned using the English accent Ritchie had envisioned for the movie, they both discovered that Pitt completely sucked at it.
He just couldn’t get it right, but the whole fiasco had a silver lining, as Ritchie created an Irish character for Pitt that he could master the accent for, and it ended up being one of the most iconic parts of the film.
1. He and Jolie were a serious power couple
There have been a lot of superstar power couples to dominate Hollywood over the years, but none even hold a candle to Brangelina.
From the time the two got together until the time they split up, the tabloids were obsessed with documenting every facet of their relationship.
It’s obvious that from a showbiz perspective, Brangelina were a power couple at the top of the food chain, but it’s true financially as well.
At one time, they hit fifth place in the Forbes list of the most financially successful couples of the year, which was predominantly dominated by musicians and those working in tech.
As for what that roughly equates to in terms of money, in their highest earning year as a married couple, they collectively earned 34 million dollars.
Since then, neither Pitt or Jolie have managed to hit those heights, proving that sometimes you really are better together.