Jennifer Aniston Vs Angelina Jolie: 20 Photos That'll Make Brad Pitt Sad

First, there was Bennifer. Then there was Brangelina. And while Bennifer and Brangelina may not have lasted, there is definitely a common denominator between the two of them. And that common denominator is none other than Brad Pitt. However, since Jen and Angelina out of the picture, seeing them again can get Brad wondering what could’ve been.

Whether it involves wearing a French maid outfit, setting records on IG, or jet skiing in a bikini, there are certain photos of Jen and Angelina that might happen to elicit a not-so-nice response from Brad. More specifically, these photos might get the movie star just a little bit upset because there is no denying these two ladies are looking great.

While Brad Pitt may have starred in The Curious Case of Benjamin Button, it looks like Jennifer and Angelina are actually living it. So without much further ado, here are 20 photos of Jennifer Aniston and Angelina Jolie that’ll make Brad Pitt sad.

20 New Phone, Who Dis?


You see this? This is what Jen likes to call her “you’re going to regret ever leaving me” outfit. And to be honest, can you blame her? Can you imagine how many calls and texts from exes she must get after stepping out and looking this good? Brad must really be sad.

19 Setting a Record on the 'gram


What better way to show that you are on the top of the world than by breaking a Guinness World Record for reaching one million followers on Instagram in the fastest recorded time. It only took Jen a little of five hours to accomplish this incredible feat. Take that Brad Pitt.

18 Beach Beauty


I don’t know if I’m more jealous of how Jen looks or how she is able to lounge on such a comfortable chair in the middle of the ocean. However, if you were to ask Brad, I’m sure it would be the former. Are people even supposed to look this good? Asking for a friend.

17 Award Winner


“Roses are red, violets are blue, I look amazing, and I have more awards than you.” This little poem for Jen is of course in reference to Brad Pitt. So now, not only does Brad have to contend with Jen looking this gorgeous, he also has to live with Jen having won more awards than him.

16 Intermittent Fasting


Wow! Where to even begin? That glow. Those arms. Those legs. Whatever Jen is doing, it is working. But what’s her secret? According to People.com, Jen does intermittent fasting. I guess going without food for so long is the secret to looking that good. Now I’m kind of getting hungry though.

15 French Maid


Bonjour mademoiselle. Well, that’s about as much French as I know. However, I have a sneaking suspicion that Brad would be more well-versed in the French language had he seen Jennifer Aniston in her French maid outfit. I’m sure Brad just downloaded Duolingo in the app store. Très bien.

14 Ms. Aniston May See You Now


At least we now know that if they were to ever make a female version of 50 Shades of Grey, Jennifer Aniston would make the perfect lead. Now if only there were a comparable male lead… I would say Brad Pitt but he’s probably too sad from seeing Jen look this good.

13 All Smiles


The best way to make an ex jealous is not only to look good, but to show you’re happy. And Jen pretty much has the looking good part down pat. But what’s even more important is how happy she looks. That million-dollar smile shows that she’s in a better place now than ever before.

12 Netflix Queen


Sure, Brad may be starring in Ad Astra, but Jen is breaking records. Specifically, Netflix records. Jen broke the Netflix viewing record starring alongside Adam Sandler in Murder Mystery. According to engadet.com, Murder Mystery was streamed by over 30 million accounts on the first weekend. That is no small feat.

11 Cover Girl


Well, if Brad wasn’t upset before, seeing Jen on the cover of Bazaar ought to do the trick. I mean come on, let’s be real about this. I think if anyone saw their ex on the cover of one of the biggest magazines in the world, and looking this fabulous at the same time, they’d be sad too.

10 Mrs. Smith


Please excuse us while we pick up our jaws from the ground. I can definitely see why Brad Pitt started seeing Angelina Jolie while filming Mr. & Mrs. Smith. I mean come on. Just look at that outfit. All that’s missing are the whips and chains. Brad must love his leather-clad women.

9 Blonde Bombshell


Let me ask you a question. What’s better than Angelina Jolie? A blonde Angelina Jolie. Sure, this blonde look was back in 2002 from the movie Life or Something Like It, but I doubt that matters to Brad. Angelina as a blonde can definitely give Marilyn Monroe a run for her money.

8 Queen Of The Ocean


Angelina Jolie, smiling in a bikini, while riding a jet ski is the ultimate summer vibe. Then again, I’ve never seen someone ride a jet ski and not smile, but still… I can’t imagine Brad Pitt seeing this and not getting a little sad. He must miss those summers together.

7 Red Carpet Ready


Wow! Who could forget that famous Academy Awards dress where Angelina showed just the perfect amount of leg all the way back in 2012? We were so innocent back then. And I know one person who can’t forget. Mostly because he was with her that night. And that person is Brad Pitt.

6 By The Sea


I would venture to guess that if there were one movie that would make Brad sad, it would have to be By the Sea. By the Sea was written and directed by Jolie and this was the last movie that she and Brad will most likely ever star in together. In fact, I’m getting a little choked up myself.

5 How Bazaar


Angelina Jolie was pretty much made for magazine covers. And I think Harper’s Bazaar definitely made the right choice. Then again, any magazine would make the right choice by having Angelina on the cover. It must be hard for Brad to pick up a magazine with Angelina’s face on it and not be a little sad.

4 Queen Of The Nerds


Angelina Jolie is absolutely crushing it with fantasy movies. She just starred in Disney’s Maleficent: Mistress of Evil, which of course was the sequel to Maleficent. And now, Angelina is going to be starring in the upcoming Marvel Studios movie, Eternals. If Brad doesn’t want to get sad, he may want to avoid movie theaters for the coming months.

3 Girl’s Night Out


As a recently divorced man, there is probably nothing that would make Brad Pitt sadder than seeing a picture of his ex-wife and their kids having a great time at a red-carpet event without him. And that’s just what happened as Shiloh and Zahara were all smiles while being out and about with their movie star mom.

2 Purple Goddess


When Angelina isn’t sporting her unnaturally large cheekbones from Maleficent: Mistress of Evil, she’s conducting press tours for the film. And the thing about press tours is that you are meant to promote your film as much as possible. Therefore, there is no doubt that Brad has been seeing these gorgeous photos of Angelina everywhere.

1 Natural Beauty


To be quite honest, any picture of Angelina would make someone sad because she’s just so stunning. It’s as if a mad scientist concocted her in a laboratory. From her eyes to her lips, to her cheekbones, she is a goddess. And when Brad sees a picture of her eating strawberries like this, there’s no doubt he’s going to be sad too.

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