The 15 Hottest Women Brad Pitt Dated Before Angelina Jolie

So by now everybody and their mother knows about Angelina Jolie and Brad Pitt's divorce. The couple got married two years ago but have been together for the past 12 years. Together they have six kids and have traveled the world and lived as a family. A lot of fans are torn about the news, while some people believe it to be karma for how the relationship started. Others are simply devastated by the thought that true love in Hollywood probably does not exist.

It has been years since Pitt has been on the market and before his back to back marriages, Pitt was quite the player. We at TheRichest thought it would be a great idea to take a walk down memory lane and see who were the hottest women Brad Pitt was linked to before he tied the knot with Jolie. This list goes back to before Pitt became the heartthrob sex symbol he is today and let us be the first to say, he has had quite the interesting dating resume. From tall girls to short girls, blonde girls to brunettes, Pitt is a lover of beauty without a specific type. Though as you'll also learn, that included courting a 15-year-old when he was 25!

These are the fifteen sexiest ladies Brad Pitt has dated and now that he is single we can't wait to see who gets added to the list.


15 Jill Schoelen

Via nypagesix

The first time Brad Pitt proposed to anyone, it was to the actress Jill Schoelen. Schoelen is most recognized for her roles in The Stepfather, Popcorn, and Phantom of The Opera. The two began their romance on in 1989 when the starred in Cutting Class. This was one of Pitt's first big movies and although he went on to reach stardom she never quite got to his level (not many people do). The flame between the two burned out as quickly as it ignited and three months later they called it quits. Believe it or not Schoelen was actually the one that dumped him, for another man to be precise.

Brad Pitt has opened up about his first engagement saying "She called me up in Los Angeles and was crying on the phone. She was lonely and there was a huge drama. At this point, I had $800 to my name and I spent $600 of it getting a ticket from Los Angeles to Hungary to see her." Let's just say we are sure that the actress regrets her choice.

14 Geena Davis

Via blogspot and fashionisto

Before we get too deep into this list, let us just say that Pitt has a bit of a dating pattern, he dates women he makes out with on screen, and Geena Davis was one of those women. Rumor has it that the couple dated for a little over a year and kept it secret the entire time. The pair never walked a red carpet together, or even went public with their relationship. The two worked together in 1991 on the incredible movie Thelma and Louise, which ended up becoming the movie that launched Brad Pitt into being viewed as a sex symbol.

For those of you who have seen the movie, you know exactly which scene we are talking about. Davis went on to have a pretty good career, appearing in shows like Grey's Anatomy and films like In a World. Davis is also part of the cast for the television show The Exorcist, which is currently in post-production. Although Thelma and Louise was considered Pitt's breakout role, the actor was only paid $6,000 for his part. I think it is safe to say since then he has earned quite the raise.

13 Sinitta


Believe it or not, Brad Pitt did not only date actresses. Sometime in the 80s the heartthrob dated British pop star Sinitta. Most of you probably recognize her as being Simon Cowell's ex-girlfriend, but she is, in fact, a pretty talented singer. Her biggest hits include "So Macho," "Toy Boy" and "Match My Broken Heart."

The British superstar was discovered by Cowell, so you can imagine she has had quite the interesting career. The beautiful Sinitta and Brad Pitt had a pretty high profile relationship and dated for more or less two years. The pair had a real relationship, it just came before Brad Pitt reached the levels of fame he has today. Sinitta has spoken openly about her past love saying, “He was beautiful with the most beautiful body, he was fun, he was young and very sweet.”

Looks like Pitt won't be getting any angry breakup songs from her.

12 Shalane McCall

Via dailymail

Brad Pitt had some questionable dating choices, Shalane McCall being one of them. The reason we say that is not because she is not beautiful, because, look at her, she clearly is. We say this because the couple began their love affair when McCall was 15 and Pitt was 25 years old. Brad met the teenager in 1987 while acting together. The show, which was titled Dallas, was a huge success and McCall ended up being Pitt's first on-screen kiss, and as we all know it sure as hell wasn't his last. The relationship was not long-lived and very few details in regard to it have been exposed. However, there is some sort of proof of their relationship. Numerous photos of the two are all over the internet, and even if the ones above appear to be of a promotional nature, it still shows the two getting close.

It is safe to say that McCall hit her career peak at fifteen when she was dating Brad Pitt. The actress has since stepped away from show business, and of course she stepped away from Mr.Pitt as well.

11 Juliette Lewis

Via huffpost

Juliette Lewis was another one of the teenagers Brad Pitt dated in his lifetime. Lewis who was 17 at the time, was ten years younger than Pitt. Lewis and Pitt dated for three years in the 90s. Lewis and Pitt still have an amicable relationship; in 2014, the posted a throwback photo of them and wished a happy birthday to her “Old friend." Since her split with the gorgeous Pitt, Lewis has worked quite a bit in the industry, appearing in films like Natural Born Killer and Due Date. Lewis has a large fan base and for those of you wanting to get a glimpse of her in a more recent project she plays Nancy in the movie Nerve starring Emma Roberts.

Lewis has opened up about her relationship with the sex icon and is surprised people are still interested in their relationship saying, “All these years later, there’s nothing I can say or divulge about Brad Pitt that would be remotely interesting to any intelligent being, I was a teenager at the time. It’s a lifetime away. I was in my high-school years and it was a wonderful, loving relationship with a fun, smart guy. Then it was over and he went on to become incredibly famous.”

10 E.G. Daily


Many of you won't recognize our next ex-girlfriend by her face as much as you would recognize her from her voice. Elizabeth “E.G.” Daily is a voice actress who has been the sound of some pretty epic characters, her most popular role was Tommy Pickles on The Rugrats. Nowadays, the actress is still in the industry, just not quite as famous as her ex Brad Pitt, but then again not many people are. The two dated in 1989 and the affair was short lived and not very public. There is not much information about the pair dating, but we know that they definitely had a fling. There are numerous photos of the young lovers together from the late 80s giving the world a little proof that there was a relationship there. Daily has remained quite quiet about their love, making us wonder what really happened between the two actors.

9 Julia Ormond

Via toutlecine

In 1994, Brad Pitt began dating the talented actress Julia Ormond. The pair obviously starred in a film together, that movie was titled Legends of The Fall. Ormond, who has had a pretty busy career, must always reminisce about those days.

She opened up about that time in her life stating that they were grooming Pitt to be the next “heartthrob” saying, “It was fascinating to me how, at heart, he’s a character actor, who’s very resistant to that [shirtless] stuff, but at the same time, [understood] that that’s what they wanted from him, or that that was what was required.”

Although she speaks more about his dashing good looks than she does about their relationship, the rumors at the time were loud and everyone in the industry knew that these two lovebirds were together. Julia Ormond is now working on some pretty exciting projects including Mary and Tour de Pharmacy, which she is currently filming.


8 Thandie Newton

Via eonline

Thandie Newton is a stunning English actress who is best known for her powerful role in the 2006 tearjerker The Pursuit of Happyness. Since then she has appeared in films like Half the Yellow Sun and Good Deeds. Newton met Pitt in 1994 on the set of the movie Interview with a Vampire. Pitt had quite the year in 1994, dating not only Newton but as previously mentioned Ormond as well. The actress was fairly new to show business at the time and their relationship lasted more or less a year. The reason for their split is still unknown but what is known is that the relationship ended amicably. She may not have been the most significant relationship in Brad Pitt's life, but she sure as hell was one of the prettiest women he has dated. And if you aren't convinced by this point, it's clear that Pitt has dated a lot of pretty women.

7 Robin Givens

Via blick

Surprise, surprise, Brad Pitt dated yet another one of his co-stars. Robin Givens also known as Darlene Merriman was one of the numerous women Pitt dated quickly in the 80s. Although we aren't exactly sure how long they dated for, we can assume it was about a year. At the time, Givens was married to the iconic fighter Mike Tyson. Tyson has opened up about his wife's infidelity with Pitt saying “During our divorce, we were f*cking. And one day, I’m going to her house to bone her again and no one’s home, and I’m leaving and she’s pulling up with Brad Pitt, and I’m sad because I’m not going to get any more...., He wasn’t Brad Pitt back then. He was just some little beach-bum-looking dude. ‘Hey dude’ kind of guy. He was probably selling his body for money or something, I don’t know, he was very pretty.” Now that is a pretty funny scene to picture.

6 Claire Forlani

Via theplace2u and eonline

In 1998, Claire Forlani co-starred with Brad Pitt in the fantasy film Meet Joe Black. The two did not try to make their relationship a secret, showing up to the film's premiere hand in hand. Forlani has a unique beauty and a captivating essence, which is probably what Brad Pitt was attracted to. Currently Forlani is filming a tv movie titled Crystal Inferno and has appeared in films like Another Me and Precious Cargo. The couple dated for more or less a year and it is also said that his ex-wife Jennifer Aniston was his rebound girl after he and Forlani called it quits. Not much besides what was previously mentioned is known about their time together.  That being said, we do know that Forlani is a knockout and worked on set with Pitt, which seems to be his idea of a perfect match.

5 Katja Von Garnier

Via caak

When it comes to beautiful women that Brad Pitt has taken to bed, Katja Von Garnier is without a doubt one of them. After ending a high-profile relationship, Pitt briefly dated the gorgeous and talented german director in the late 90's. In 2009, there names popped up in the press again, this time because they were seen chatting at the premiere of the film Inglourious Basterds. Rumors quickly began circulating that the two were having an affair behind Angelina Jolie's back, but nothing ever came of the rumors. Garnier was not the typical kind of girl that Pitt went for however, they made quite the cute couple. The two parted ways, but as we have learned will always have respect for one another. You can only hope Pitt and Jolie will feel the same way about one another.

4 Demi Moore

Via lifeanddeathprez and laceswan

Sometime in the late 90s, Demi Moore and Brad Pitt were rumored to have been knocking boots. The relationship was never confirmed but rumours ran wild about the two having a steamy love affair. Moore is one of the only women that Pitt dated that was at the same level of fame that he is at. Moore, who is both stunning and talented, has also dated some of Hollywood's most elite men including Ashton Kutcher, Bruce Willis, and Ryan Reynolds. When you consider she has appeared in classic films such as Ghost, G.I Jane and A Few Good Men, it is easy to see why she was such a catch. Moore is a superstar and it comes as no surprise that at one point or another these two actors found one another. The real shock is that they didn't meet on a movie set!

3 Christina Applegate

Via closerweekly

Christina Applegate is one of the most cheeky and adorable women in show business. Appearing in films like Vacation and Anchorman, Applegate is one of those rare people that is super beautiful but also hilarious and down to earth. This year, she was in the film Bad Moms and currently her latest film Crash Pad is in post production. There once was a time, before Brad Pitt was the man he is today, that he and Applegate dated. The year was 1989 and Applegate was a much more popular celebrity at the time. When Pitt took her to the MTV Movie Awards, not many people knew who he was and at the end of the night, Applegate left the award show with another man...ouch. Years later, Applegate opened up and stated that she regretted making that decision. It makes sense that she would. After all, who wouldn't regret giving up a shot at being with Brad Pitt?

2 Gwyneth Paltrow

Via bustle

Of course, in typical Brad Pitt fashion, he met ex-girlfriend Gwyneth Paltrow during the filming of Seven. Paltrow was only 22 years old at the time while Pitt was 32 (clearly he likes younger women). The two had an extremely high profile relationship that lasted about three years. We think that this was one of Brad Pitts best matches both physically and popularity wise. The relationship started in 1994 and Pitt even proposed to the gorgeous actress!

Paltrow opened up about the very public relationship on The Howard Stern Show, saying: “I definitely fell in love with him. He was so gorgeous and sweet. I wasn’t ready, and he was too good for me.”

The two are still friends today, but who knows now that they are both single maybe they will find each other once again. Both Pitt and Paltrow went off to have incredibly big careers, so we are sure they have run into one another on more than one red carpet event.

1 Jennifer Aniston

Via nydailynews

Is anyone surprised that Jennifer Aniston is number 1 on this list? Aniston and Pitt were together for seven years, five of those years they spent as husband and wife. In 2005, the marriage ended when he reportedly left his wife for Angelina Jolie. Pitt claims he was trying to force something to work, that simply was not working. Pitt described his relationship with Aniston, saying “Sitting on a couch, holding a joint, hiding out, I think that my marriage had something to do with it. Trying to pretend the marriage was something that it wasn’t.”

Aniston has also opened up about their very public breakup saying “He just wasn’t there for me.” Courtney Cox, who is Aniston's best friend and co-star on the show Friends opened up about her besties marriage with Brad and has said “I don’t think he started an affair physically, but I think he was attracted to [Jolie]. There was a connection, and he was honest about that with Jen.” Right now, with Brad's divorce made public, the world is dying to hear what ex-wife Aniston has to say about it.


Give TheRichest a Thumbs up!

More in Entertainment