With a combined net worth of close to $500 million, there may not have been a bigger power couple in Hollywood than Brad Pitt and Angelina Jolie. The two have both been considered to be some of the sexiest people in Hollywood, but news dropped in September that this romance has come to an end.
Many people recommend when you go through a breakup to try and go "no contact" and not look at photos of your ex or think of your time together. Much harder when not only do you have kids together, but there are tons of photos out there that will pull at your heartstrings. Whether they're sexy photos, photos of their children together or photos from their first (and last) time on the red carpet, we're sure Pitt wouldn't be able to make it through this list without shedding at least one tear.
Remember that outfit she wore in Mr. and Mrs. Smith? If you don't know what we're talking about, be prepared to see something that you can imagine Pitt won't easily forget.
All that and more when you check out 15 Photos That Will Make Brad Really Miss Angelina.
15 Can't Keep Off That Booty
There may not be many men out there who are going to blame Brad Pitt for grabbing a hold of Jolie's booty, as he is clearly doing in both photos. But c'mon man, you need to understand that there are going to be cameras everywhere and there is no way you're going to be able to do that subtly!
The first photo on the left comes from the premiere of Ocean's Thirteen. The movie was honestly disappointing, but it's clear that Pitt was not disappointed in Jolie's decision to wear that yellow dress.
The one on the right came several years later, during the premiere of The Tourist. Perhaps Pitt just wanted to remind Johnny Depp, who starred in the movie, who she was going home with!
14 The Twin Baby Photos
There are a lot of photos on this list that are going to be enough to leave Pitt up at night wondering how he let the gorgeous Jolie slip away. But no photo may tug on his heart strings harder than the above photos which were sold to People magazine for a record $9.7 million. It was the first photos of their newborn twins, Kox Leon and Vivienne Marcheline.
When talking about the pictures, one of the magazine insiders was quoted as saying "Brad and Angelina are the dream couple of the glossy magazine world and we expect to triple our circulation because of the public's fascination and interest in the couple and their children."
Looks like that dream couple turned into a nightmare eventually!
13 Proving She Was Sexy Before Pitt
Angelina Jolie definitely was still one of the sexiest women in the world after she got hitched to Brad Pitt, but looking at a younger photo like the one above is proof as to why she was such a catch! The photo shoot, while not dated, clearly looks to be done long before Jolie made it big in Hollywood. It's clear that purple is her color, and having a sheer tearaway like you see on the bottom makes it perfect for some fun photos; as seen in the 2nd photo in which it's used to cover up her entire body.
It's clear no matter how she chooses to wear it, Jolie pulls off the look. Call us crazy, but doesn't she look super similar to Mila Kunis?
12 Showing Off For Her 32nd Birthday
How do you plan on celebrating your 32nd birthday? For Jolie, she decided why not spread out for the talented photographers at Esquire. The photos were taken back for the 2007 issue, so you can imagine Pitt had plenty of enjoyment looking at all the photos and the outtakes from the day.
As a fun bit of hindsight, during the interview for the magazine she was asked how she balances life with her children and Pitt, responding with "Some people have their lives together and then they have their children. Brad and I are starting with the children and are planning to have our time together in our later years.”
Guess she didn't see this divorce coming!
11 Showing Off The Value Of Mirrors
George Holz is one of the most talented photographers out there, but when you get to shoot gorgeous models like Angelina Jolie, you can imagine that makes your day all the easier. When talking about his experiences working with Jolie, Holz said "No huge entourage. It was just one of those monumental shoots where you really feel you’ve connected. You hope to have those days.”
Holz even admitted that Jolie invited him to take part in a cross-country trip she was doing with the Hell's Angels, but the trip never turned into a reality. We'll be honest, the back tattoo is definitely not the sexiest thing in the world, but kudos to the photo shoot for finding a clever way to utilize the mirror!
10 Photos From The Movie The Met On: Mr. and Mrs. Smith
You need to hope that in your relationship you have some fun photos from when your relationship was just getting started. For Pitt and Jolie, they had the good fortune of starting their relationship after they were working on the movie Mr. and Mrs. Smith together. Considering they were two of the sexiest people in Hollywood, you can imagine the movie was full of plenty steamy moments. While the above photo on the left is not the steamiest, there's something about the loving look and holding each other close aspect, that you can imagine will pull extra hard at Pitt's heartstrings.
Plus you know, there's definitely nothing wrong with taking a look at Jolie as she stands there looking like a dominatrix, as in the photo on the right!
9 Their Wedding Photos
How are you going to be able to complete a list on photos that will cause some heartache, and not include a photo of their wedding that occurred back in 2014. It was a smaller affair, with only 20 guests present, and the focal point being on involving their six children in a variety of roles. This included Pax, who is now 12, baking the cake.
When talking to People about their wedding, Pitt said "It was important to us that the day was relaxed and full of laughter. It was such a special day to share with our children and a very happy time for our family."
Even though things aren't ending the way they had planned, at least you need to hope that's a happy memory!
8 Their First Time On The Red Carpet Together
Angelina Jolie and Brad Pitt were hush-hush about the start of their relationship, but by the time the red carpet came around for The Good Shephard, the word was out. The movie starred Jolie, and it was in December 2006 that the two first stepped out on the red carpet as an official couple.
The photo on the right features the two exchanging words during one of the first premiers for their movie Mr. and Mrs. Smith. It was there they started their romance, but still did not want to broadcast that to the world (you know, due to the whole being married to Jennifer Aniston thing!)
7 Their Last Time On The Red Carpet Together
Nothing makes the pain of a relationship sink in quite like looking at photos from when you and your partner were still happy. You now have to wonder if back in November 2015 when Pitt and Jolie made their last public appearance on a red carpet if the cracks were already forming.
The two were promoting the movie By The Sea which starred both of them, so kind of hard to get out of promotional duties! In case you're curious, Jolie was wearing an Atelier Versace gown and was decked out in Swarovski crystals.
6 Their 2015 Photoshoot For Vanity Fair
There is no shortage of sexy photo shoots where it's just Jolie standing there, but in 2015, Vanity Fair decided to try and take photos showing off the both of them. Easy decision when you consider they're still two of the sexiest people in the world, and just look how genuinely happy they look in the photo!
The photos were done as part of a promotion for By the Sea which was the first movie that Pitt and Jolie had teamed up on since becoming a couple. Jolie said she wrote the movie following the death of her mother, and that the two agreed to try and turn it into a movie after they got married.
The movie got ripped by critics, earning only 33% on Rotten Tomatoes, but you can hope they at least had fun filming the movie?
5 Jolie's 2007 Photoshoot For Vogue
In 2007, Vogue came calling for Angelina Jolie and when you see the beautiful photos above, you can understand why they were insistent on hiring her. The photo on the left features her looking stunning in an elegant red dress but of course she looks good in a dress! The same issue of Vogue also published photos like the one on the right, showing off a black and white and more classic look to Jolie. As an added bonus, Jolie was on the cover of the issue, which also had the caption "Angelina Jolie: Why Her Real Life Is More Romantic than Any Movie."
I guess that romance had a twist ending.
4 Eating Food In Bed
If you're going to get into the practical nature of the photo above, you'd wonder why on earth it looks like she has a gigantic red pepper in the bowl. After all, when it comes to sexy foods to bring into the bedroom, I don't think that's going to be at the top of many people's lists. But you'd be crazy if Brad Pitt didn't take one look at that above photoshoot that appears to be pre-Jolie, and instantly make sure his kitchen had strawberries on hand!
The fact that Jolie is able to look so elegant and beautiful in such a simple and classic white dress, makes her all the more appealing. Just don't get on her bad side because it looks like that ring could pack a punch.
3 Wallstreet Journal Photo shoot
Angelina Jolie is typically a pretty private person, but the release of her movie By The Sea, which you've now read about several times, saw her sit down with several companies for promotional work or photo shoots. One of them was The Wallstreet Journal, who also asked Jolie about her penchant to play action-hero type characters. Jolie responded "I did Wanted after my mother died, and I did Salt after I had twins. I don’t think it’s a coincidence that I go through these moments where I just want to pull the covers over my head, so I go get aggressive instead.”
You can only imagine the fuel she'll be feeling if she gets cast in an action movie again in the very near future. Cast Brad Pitt as the main antagonist and you've got a box office hit!
2 Her Right Leg At The 2012 Academy Awards
At the end of every major award show, the internet goes crazy debating which star pulled off the best look from the night. In 2012 after the Academy Awards, it was clear that Jolie (or shall we say, her right leg) was the clear winner of the night. Her dress, which was done by Atelier Versace, clearly left Jolie feeling pretty sexy all night long.
Though when you consider Jolie was presenting an award for Best Adapted Screenplay, can you blame her for pulling out all the stops? You also can't blame the audience who reacted with wolf whistles when she stepped out onto the stage.
1 The Family Vacation To Thailand
Wouldn't it be nice if you and your family wanted to go on a vacation and money just wasn't a factor? While Pitt won't be hurting for money, you can imagine his vacations are about to get a heck of a lot lonelier. The above photo was taken back in 2015 and shows Jolie heading to the airport along with the group of children.
Pitt and Jolie took the children on a vacation to Southeast Asia, including Vietnam, Cambodia, and Thailand. Photos that also emerged from the trip showed Jolie and Pitt enjoying a romantic kayak trip while in Vietnam. Let's hope he will be able to find someone else to help paddle the boat!
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