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15 Hottest Jennifer Aniston vs. Angelina Jolie Side-by-Sides

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15 Hottest Jennifer Aniston vs. Angelina Jolie Side-by-Sides

When it comes to love in Hollywood, Brad Pitt is arguably one of the luckiest men, if not the luckiest. He was married to both Jennifer Aniston and Angelina Jolie, who are two of the finest women in the world. But somehow, he also lost them both. When he fell in love with Angelina Jolie during the making of their movie, Mr. and Mrs. Smith, in 2005, it led to the end of his marriage with Jen. Then, after 11 years with Angelina, their marriage, too, was over. Although the reasons for Brad’s second divorce are slightly vaguer, there have been reports that it was due to his drinking, various fights about parenting and politics, and their conflicting schedules. Either way, both Brad and Angie have said that their children come first, and Angelina was granted full custody of all six of them.

But let’s take a minute to fully appreciate what a total d-bag Brad must have been to let himself lose these two amazing women that most men would kill to be with. When you see the following 15 side-by-sides of Jen and Angie, it’ll become even more apparent that Brad is a pretty big idiot for losing out on them both. Keep reading to see what I mean (and to revel in the sight of Jen and Angie looking oh-so-gorgeous, as always).

15. Brad’s Brides

Let’s start with the thing that began all of the drama and all of the never-ending comparisons between Jen and Angie: their weddings to Brad. Both of his brides look so beautiful and neither in an over-the-top, gaudy, bridezilla sort of way. His two brides are the picture of elegance and happiness in these photos and look so at peace on the day of their nuptials. It’s almost bittersweet to look back and know that both women would end up divorced from him, the man they both loved. But it’s probably hardest for Brad to see these images, knowing better than anyone what he lost. If anything, the pictures will hammer it home. Jennifer was quoted as saying, “Marriage is wonderful.” And Angelina said, “It’s weird to be married; you kind of lose your identity. You’re suddenly somebody’s wife. And you’re like, ‘Oh, I’m half of a couple now. I’ve lost me.'”

14. Hot Wives

Obviously taken for a photo shoot are these stunning photographs of both of Brad Pitt’s ex-wives. Both have been featured on countless magazine covers, in magazine spreads, and in advertisements for various products, promotions, shows, and films. But I’m willing to bet these photos are among the most beautiful. They both look a bit younger than they do now, so these were probably taken a few years back. They were probably taken, in fact, when Brad was still with one or the other, making him even more the idiot. What kind of man lets himself lose out on either of these perfect women? Unless a woman is a complete b*tch or horrible partner — which I doubt either Jen or Angie was — he would have to be nuts to let either of them slip through his fingers.

13. Goddesses in White

Here, Brad’s exes wow in white. Both are a picture of elegance, almost goddess-like, in flowing white gowns. They even pose the same way, exposing quite a bit of their left legs with sexy slits in the dresses. Angelina’s ensemble is a bit more conservative, with the long sleeves and less of her chest exposed, while Jen bears more cleavage and has spaghetti straps. Both looks are eloquent, however, and this is a great side-by-side to show that even though Jennifer and Angelina are very different people, they share more than just an ex-husband; they share a sexy elegance. Sometimes, like in these photos, they even share the same exact stance and smile. Maybe they’re not so different after all, and maybe that’s why they both wound up with Mr. Pitt.

12. Babes in Black

Jen and Angie look just as great in black as they do in white as evidenced by these photos. Both wearing little makeup and with their hair worn casually down, they give off a whole different vibe here. And once again, they prove that just maybe, they’re not all that different. They seem to often have similar styles, after all! With Angie’s exposed tattoo, black leather strapless top, and slightly messier hair than Jen’s, it appears that she’s out and about and not doing anything too important. But the nicer fabric of Jen’s top and the fact that she’s wearing fancy earrings lead me to believe she could be at some formal event. Still, despite the fact that Angie is much more casual than Jen in these photos, the two women still manage to look quite similar.

11. They Smolder

Eat your heart out, Brad! He must be kicking himself looking at these hot photos. These photos of Jen in a tight black leather bustier and Angie in a black, Grecian-style top with flames behind her are both very sexy images of the ones he let get away. Both Jen and Angie bring it in these photos, making it easy to see why they’ve both consistently been ranked the hottest, most beautiful, etc. by charts around the world for years. Perhaps, part of it has to do with the fact that they’re both so damn good at that smoldering stare and those tough but pretty smiles. In these photos, Jen rocks some tousled, wind-blown locks, and Angie works that pout she’s so well known for. Both women do their thing, and good ol’ Brad is probably dying inside knowing that once, he had them both, and now, he has neither.

10. Cover Girls

As we know, Jen and Angie have graced the covers of so many magazines over the years and for good reason. Whether it’s the cover of some silly gossip magazine with rumors of their love lives, or a more classy magazine like Vogue, for which they both posed for above, Jennifer Aniston and Angelina Jolie have always been favorites to sell magazines with. Vogue had them both in a sexy red, posing for their individual covers. Jen wows sitting on a rocky beach wearing a long, fitted, scarlet dress and natural makeup. Angie poses in a deep red, off-the-shoulder gown in the desert — an image that lends itself to her reputation of being a citizen of the world. Angie loves to travel the globe, especially to exotic locations like the Middle East, Africa, and Southeast Asia. Since Jen loves the beach (and has her own fragrance line made up of beachy scents) and Angelina loves exotic locales, Vogue did a good job picking the backgrounds for these cover shoots.

9. Candid Comparison

Even something as simple as stepping up onto the curb from the street can get Jen and Angie compared in a side-by-side. The fact that they were both married to Brad Pitt, who was once Hollywood’s biggest heartthrob, makes them a target for being compared for pretty much anything –– including walking down the street. And so we’ll compare. Yet again, these two very different actresses look remarkably similar — not in their facial features, of course, but in their outfit choice, stance, and hair and makeup choices. Both wear earthy-colored, tight midi dresses, natural-colored heels, and their hair (which, I might add, is the same length and similar shades of light brown) is styled the same. The only real differences are Angelina’s large purse and sunglasses and that Jen is holding a drink.

8. The Sex Symbols Face Off

If Brad wasn’t kicking himself already, he will be now at the sight of his two ex-wives in these photos. This side-by-side is a case of candid photo versus professional photo, obviously, but both women still look stunning. Both also look topless, only adding to the sex appeal. Both have been praised for their extraordinary bodies, and both have thoughts on being thought of as uber sexy. Jen says, “Nobody thinks of themselves as sexy, really. Some days you go, ‘Hey I’m not doing too bad today.’ But if you try and be sexy, you’ll never be sexy.” For her part, Angelina says, “I don’t see myself as beautiful because I can see a lot of flaws. People have really odd opinions. They tell me I’m skinny as if that’s supposed to make me happy.”

7. Black Ball Gowns

Brad’s ladies in black once again work the leg slit, this time in their flattering black ball gowns at different formal events. Jen just looks like her usual sexy self, but Angelina, always fairer-skinned than the tan Jennifer, almost looks like she’s channeling her inner Maleficent with that red lipstick. Of the character she played in the 2014 movie Maleficent, Angelina says, “Maleficent has suffered abuse in the past, and there’s a reason why she is now as furious as she is. And I think that children who have been outcast and abused in any way will relate to her. She has all these facets. And that is interesting.”

6. Jen and Angie Talk Looks

In bed is definitely one way that Brad Pitt was used to seeing these two, and although in real life, they weren’t all photoshoot-ready like they are here, there’s no doubt that Jennifer Aniston and Angelina Jolie looked just as pretty without makeup just crawling into bed for the night or just waking up in the morning. Sometimes, natural and vulnerable is the prettiest look of all. But even they aren’t immune from feeling self-conscious or less than thrilled with their looks — looks that every other woman in the world would kill to have. Jen says,” You know, I’ve got wrinkles on my forehead and smile lines… I’m sprouting more than one wonderful grey hair.” And Angelina admits, “I am odd-looking. I sometimes think I look like a funny Muppet.”

5. Class Acts

Looking classy in pantsuits, Jen and Angie go head-to-head in yet another side-by-side comparing them. But there is no comparison, really, because they both stun. Angie keeps it simple with a low-cut white jacket and matching pants. She wears natural makeup, pulls her hair up, and wears no jewelry. The less-is-more look works for her of course, only drawing more attention to her beautiful face. Slightly fancier, Jen also works the pantsuit, dressing it up with layered gold necklaces and a clutch. But her makeup is light, too, and her hair is also pulled back. Altogether, these looks are both different and similar and neither woman looks better than the other. I wonder which Brad would prefer?

4. Ample Assets

In this photo, Jen and Angie show off their assets. Both have ample cleavage, although as of 2013, Angelina underwent a double mastectomy after a genetic test revealed she had an 87% chance of developing breast cancer at some point in her life. She then had reconstructive surgery to have a more natural-looking chest. Obviously, this photo of her was taken when she was quite a bit younger as was this photo of Jen. Cancer has touched both women’s lives and taken loved ones from them both. Angie says, “I do not feel any less of a woman. I feel empowered that I made a strong choice that in no way diminishes my femininity.” Jennifer says, “Cancer affects all of us, whether you’re a daughter, mother, sister, friend, coworker, doctor, patient.”

3. Opposites

Now, here’s a side-by-side comparison of Brad’s two ex-wives that actually highlights their differences. Angelina is known around the world for being a sex symbol; in fact, she oozes sex appeal. She’s quieter and takes on more serious roles and when compared to Jen, seems darker somehow. Jennifer, who became famous playing the ditzy character of Rachel on Friends, is lighter, funnier, and seems to not take life as seriously as Angelina might. Jen usually plays comical roles like those in Horrible Bosses, The Switch, and We’re the Millers (however, she has given some surprisingly great “dark” performances in movies like Cake and The Good Girl). Angelina typically plays a serious character such as Mariane Pearl in A Mighty Heart, but she does a lot of action films too.

2. Their Beginnings

In these photos, both Jen and Angie were in their prime, and their careers were only beginning to take form. Neither probably knew just how successful they would become. Angelina started her road to stardom in the mid-nineties in smaller films, and her major break was playing Amelia Donaghy in 1999’s The Bone Collector alongside Denzel Washington. The same year, she starred with Winona Ryder in Girl, Interrupted. And the rest, for Angelina, was history. Before Friends, Jennifer had recurring roles on the shows Molloy and The Edge. When she auditioned for the role of Monica on Friends, she had no idea it would change her life. She wound up playing Rachel, and we couldn’t imagine it any other way.

1. Avoidance At All Costs

This is Angelina Jolie and Jennifer Aniston now. They’ve aged, but they’ve done so gracefully, and Brad (or any man, for that matter) would’ve still been pretty damn lucky to have called either of them his. Both looking more mature and elegant in their recent years, they were both at the 2015 Critics Choice Awards when these photos were taken. Several articles noted that the two obviously avoided one another on the Red Carpet and sat on opposite sides of the ballroom. One article said, “The duo have not been at the same awards show in six years and famously have never spoken publicly since Jolie and Aniston’s then-husband Pitt filmed Mr. & Mrs. Smith together in 2004 and fell in love… each actress’[s] team made a concerted effort to keep them apart — but the pair almost bumped into each other a few times.”

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