One of the most popular actresses in the world for decades at this point, from the time that Jennifer Aniston became a superstar due to her involvement in the show Friends, people have liked her. That is partially due to the fact that she can be very charismatic and amusing when she appears in a movie or show, but it also has a lot to do with her looks. We say that because she is a beautiful woman, for sure, but also carries herself like she isn’t overtly egotistical too.
Still a big deal to this day, her career has shifted as of late since she is taking on more outrageous comedic roles in movies like Horrible Bosses, We’re the Millers, and Office Christmas Party. We totally support her efforts to extend her image but it does make us think back to a time when her roles were more innocent for the most part. Realizing that is what inspired us to put together this list of twenty must-see photos of Jennifer Aniston prior to middle age.
In order for a photo to be considered for inclusion here, the first prerequisite is that Jennifer Aniston can be seen and looks great. That means that the inclusion of people other than this popular actress will have zero effect on the placement of a photograph on the list. Screengrabs of her from shows, movies, or other media appearances are fair game as she has a history of looking incredible wherever she goes, and we’d be fools to exclude them. Of course, for the purposes of this list, we’ll be excluding any shots of her that were taken once she was middle-aged. Everyone’s definition of what that consists of is going to be different but we’ve opted to choose turning forty as the line of demarcation, so we tried to ensure that every photo listed here was taken before Feb 11th, 2009.
20 That Look
A shot from the time period in which Jennifer Aniston had only been a huge star for a short period of time, in this image, she is even sporting the “Rachel” look, the haircut her character in Friends made famous. While there were millions of people that looked at her and wanted to emulate her image–which we can’t blame them for since she looks great–in our book, we’re more than happy to just enjoy the view. Also wearing a top that exposes much of her midriff and her arms, as well as looking wonderful on her, there is still another aspect of her that we’re most bowled over by. We say that because the look in her eye here is amazing since it communicates the idea that she sees the person looking at the photo as someone she wants to spend time alone with.
19 Rolling Stone Cover
An actress that is no stranger to courting attention, Jennifer Aniston has appeared on many magazine covers which has helped to ensure that she remains the talk of the town with some regularity. Perhaps her best-known appearances involve Rolling Stone Magazine whose front page she has adorned many times over the years, including once without a stitch of clothing on while laying on her stomach. As great as that was, in this case, we’re including this shot of her from a 2001 issue in which she wore an elaborate top with jeans. The reason this shot stands out so much is the awe-inspiring view of her midriff that is on display. Always an attractive woman on the face of it, it is marvelous to see how tight her stomach is.
18 Exquisite Beauty
An actress that seems to be able to pull off practically any look it seems, we’ve already touched on the fact that Jennifer became well-known for a specific hairdo. Still, she has been around for more than one decade at this point, and during that time, the world has seen her sporting a number of different cuts to varying degrees of success. For instance, here she is sporting bangs which we have to admit is a style of cut that doesn’t always appeal to us. That said, on a woman like Jennifer, it seems like her hair can do almost no wrong, and we love this shot for sure. Of course, the fact that we get to check out the rest of her here helps a lot, especially when it comes to her lovely legs.
17 2004 Golden Globes
During her career, Jennifer Aniston has been up for a lot of awards and is an entertainment personality which has led her to be a mainstay of red carpet events, much to the enjoyment of those in attendance. Nominated for Golden Globe Awards three different times in the past, her work on Friends saw her in the running in both 2002 and 2003, and she won in the latter case. Seen here at the 2004 Golden Globes event, it seems obvious that she wanted to own the night and decided to dress in a way that would make that possible. Wearing a dress that is absolutely exquisite on her, we love the way its cut looks on her, as well as the view of her cleavage it provides us.
16 French Maid
We’re going to try to be as up front as possible with this image. Obviously, we have no problem at all with enjoying the human form and think you shouldn’t either. But at the same time, there are some cultural tropes in that area that don’t always make sense to us. For instance, there are a lot of instances in which the whole French maid thing just doesn’t work for us, in part because it often feels like they are trying too hard. Then, we see a shot of someone we think is hot sporting it, and we totally understand the appeal once again, even if they don’t seem to be totally committed to the outfit. Here, we have a screengrab of Jennifer from the film Friends with Money. We haven’t seen the movie in question but knowing that she looks this good in it makes us want to.
15 2003 Emmys Dress
The second and last shot of Jennifer on a red carpet at an awards show, in this case, the 2003 Emmys, she seems to be totally relaxed but she is an actress and we have to imagine that that isn’t entirely the case. First off, she was in the running for a trophy that night and must have been at least a little bit nervous about whether or not she’d win and have to give a speech. Secondly, the fact that these events are a huge deal for celebrities whose careers rely heavily on attention to continue, means that someone like her must do what they can to turn heads. In the latter case, it makes sense that she could breathe at least a little bit easier since she looks so great in that dress that she knew all eyes would be on her.
14 White Outfit
Once you become an actress of Jennifer’s caliber, there is a huge part of your job that has nothing to do with actually playing a part while on set. Most of them have to do with promoting themselves and the projects they are part of, including the likes of interviews and photoshoots. When it comes to the latter of those two, this is one of the best images of Jennifer from a photoshoot in our view. One of the major reason why we like this image so much is that it seems far simpler than others, especially when you take a look at her simple white outfit and her slightly disheveled hair. Seeming far more natural than many shots of her, including those on this list, we love seeing proof that she doesn’t need anything overly elaborate to look fantastic.
13 Yellow Dress
Going from one extreme to another, in the last shot, we appreciate her simple look but she looks quite the opposite here and it is still a thing of beauty. Wearing far more makeup than we are used to seeing her have on her face and a dress that fits that feel too, due to the extreme cut of its plunging neckline, there is an obvious theme here. Yet, somehow in our mind, the over-the-top aspects of this shot serve to drive our attention to her natural body since her beautiful face completely stands out here. On top of that, there is no doubt that the perspective of her chest here is bound to drive a lot of viewers’ minds wild with appreciation.
12 Friends Outfit
A screengrab from the show that made Jennifer a star, prior to Friends, she had been working in movies like Leprechaun or shows like Ferris Bueller, but she was largely unknown to the masses. Cast as her popular role, Rachel, a spoiled rich kid that is thrust into the world of independence she was not prepared for, fans got to watch her character mature into a strong woman. On top of that, it was a joy for millions to witness her love life and watch her on screen since she was such a desirable person. Notable for wearing outfits in the series that were emblazoned into the minds of her fans since they were so alluring, we had an endless array of screengrabs like this one to potentially include here. Yet, we chose an image of her wearing a turtleneck of all things because we were instantly enthralled by the way it fits her chest.
11 White Tank Top
One of many images of Jennifer that you may find on websites that are set up to host wallpapers, we can totally imagine why someone may choose to download this one in particular. If you are unfamiliar with the concept, these photos are meant to serve as the background on your computer’s desktop that come up whenever you turn your computer on. As such, it makes total sense that someone would want to be met with this shot whenever he/she has the computer boot up. Wearing a tank top that is tight to her body aside from a few wrinkles, that alone is enough to make this shot worth employing in our view, but we enjoy the knowing look on her face too.
10 Sleek Dress
A picture of Jennifer that looks like it could have been taken during the golden age of Hollywood, this image was actually taken for publication in a 2004 issue of Vogue Magazine. Wearing a dress that seems like a total throwback, it really makes us appreciate the idea that fashion is cyclical since we’d love it if it was cool for gorgeous women to choose to look like this. A sleek-looking ensemble that is cut to perfection to cradle every aspect of her body above her hips, that means that all of her curves are strongly hinted at. The final aspect of this image that we enjoy so much is the posing of her arms as we adore the view of her running her hand through her hair, as well as the way it accentuates her chest.
9 Open Jacket
A photo that seems like it was set up to communicate an expression of surprise, there is one thing everyone should have come to expect by now—Jennifer Aniston looks splendid. Seemingly a play on flashing you a view of their body, if you are anything like us–and we assume you are since you’re here–the idea of her showing up on your doorstep like this is a dream come true. Wearing a long jacket that is the length of some dresses in this image, if she hadn’t opened it up, this may be somewhat pedestrian. But, this is all about the tease. We say that because we’re not actually seeing all that much here–aside from part of her bra and a small portion of her flesh that we typically don’t see–but the implication is more than enough to make us happy.
8 Vanity Fair Cover
Earlier, we touched on the idea that Jennifer is strongly connected with the cover of Rolling Stone magazine, but that doesn’t mean that she doesn’t have a lot of strong relationships in that industry. Clearly a photo that was seen on the front page of Vanity Fair, this magazine was released to the public in 2004, and we have to assume that it was quickly gobbled up. Looking like she is totally at peace with her body and image here, it is hugely attractive to us that she seems like someone who knows exactly who she is and what she wants in this shot for some reason. That is to say nothing of how great of a vantage point we’re getting of her cleavage, which has (even more) to do with the ranking of this picture on this list.
7 Movie Booty
The last screengrab of Jennifer from the many movies and shows that she has been seen on over the years, you may be expecting us to have chosen a project that was a big deal for her career. Sorry to disappoint you if that is the case but that isn’t what we’ve done at all since this originated from Along Came Polly, a movie that was a mid-level success for her at best. Still, when putting together a list like this one, that doesn’t matter in the slightest since how she looks in the image is the only consideration in the criteria we’ve set up. With that in mind, this rare view of her booty is worth our weight in gold since she has a rear end that deserves a lot more praise, as is very evident here.
6 2009 Vogue Cover
A lot has been made of the changes that seem inevitable when it comes to the print industry, for good reason. But, we here at TheRichest.com aren’t too worried since we know it will continue in some form. We believe that because there will always be a demand for gorgeous shots of stunning women, and magazines are a perfect forum for that whether they are released digitally or in paper form. For instance, this image of Jennifer from the February 2009 issue of Vogue would inspire us to fork over our hard-earned money. Clearly taken at least in the previous month when she wasn’t yet forty years old, it is one of the best images of her cleavage and body as a whole we’ve ever seen.
A picture that seems a little bit pretentious on the face of it, here we see Jennifer in a dress someone seems to have worked very hard to perfect and on a couch someone must have dragged outside. On top of that, we can’t know for sure since this photo is relatively tight, but there does seem to be hints of the locale this was taken in being somewhat opulent as well. As such, it seems like a lot of work was put into the end results we’re looking at but we’re guessing that those that sweated the details are satisfied. After all, their work resulted in a rather bewitching image that features a loved star with her legs and cleavage on display and positioned in a manner that seems somewhat suggestive too.
4 Red One-Piece Cover Shot
There aren’t the tell-tale fonts on display here, which makes this look like a slightly more ordinary shot of Jennifer Aniston. But this actually is the last image on this list that adorned the cover of a magazine. Appearing on the front page of the March 1999 issue of Rolling Stone, this is another example of why that publication and this actress seem to have so much love for one another. Wearing a one-piece red outfit that reminds us of a swimsuit aside from its extensive decorative parts here, in addition to seeming fancy, it shows off as much of her as swimwear of that style does. That is a wonderful thing since we enjoy seeing as much of her as possible and this is another delightful example of why we feel that way.
If it isn’t painfully evident at this point, we here at TheRichest.com enjoy the career and looks of Jennifer Aniston a great deal. That is why we didn’t find it hard at all to populate this list with pictures of her but instead struggled to leave so many ravishing shots of her off. As such, even we are somewhat aghast to realize that we’ve only included a single photograph of her in a bikini. But at least we can rest easy because we found the best one out there. A picture that was taken of her by a paparazzo in 2004, we could go on and on about what makes it so steamy. But looking at it, we realize that we don’t have to, so let’s take a moment to enjoy it.
2 Tight Top
If you ask us, this photo of Jennifer actually serves as something of a Rorschach test since the viewer can see so much in it. For instance, at first blush, it seems like quite the innocent image as she is almost entirely covered from head to toe. However, once you look a little bit closer, there is so much to be attracted to here that it practically blows our mind. If you don’t know what we mean, then we suggest that you start out by enjoying the look on her face which exudes confidence but, more importantly, seems rather inviting, if you know what we mean. Next, the fit of her pants is so on point that it almost feels more revealing than some images where they aren’t covered at all, since it really drives the imagination into overdrive. Finally, if you’ve somehow managed to miss it, the top she is wearing is so tight to her chest that some may find it nearly impossible to look away.
1 Back View
We here at TheRichest.com have followed the career of Jennifer Aniston for a number of years, which led us to believe that we were aware of the best shots of her out there. Then, we were working on putting together this list and we came across this image, and we were totally gobsmacked that it had somehow escaped our attention in the past. Once we saw it, however, we knew instantly that we’d come across the top shot on this list, as it is a total feast for the eyes. If you question that at all, then you have to sit back and take in the glorious look at her mostly uncovered back and the look on her face as she looks back at the camera. Our favorite aspect, though, has to be the view of her chest from the side here, which is so hot that it is hard to describe in words.