It may not seem like it today, but there was a time when it looked like the Simpson sisters were set to take pop culture by storm for many years to come. For her part, younger sister Ashlee Simpson was a burgeoning pop princess who had released several songs that did surprisingly robust sales, even earning placement on the Billboard charts. Also, an actress who was seen in shows like 7th Heaven, Melrose Place, and more, she also had roles in movies like The Hot Chick and Undiscovered. On top of all that, she played Roxie Hart in productions of Chicago that were put on in the Hollywood Bowl, Broadway and The West End over several years.
Clearly the more successful of the two, Jessica Simpson led the way for the pair with an even more successful music career before becoming an actor in her own right. A star of movies like The Dukes of Hazzard, Employee of the Month, and Blonde Ambition, she got the coveted role of playing Daisy Duke on the big screen. However, with all that under her belt, it is arguable that her biggest accomplishment came as part of an insanely popular “reality” show. One of the stars of Newlyweds: Nick and Jessica, the show was beloved mostly because of her lovably naïve nature. Realizing how important these two women were for a time and the fact they were known for their looks, inspired us to put together this list of twenty hot photos of the Simpson sisters in their prime.
In order to be considered for inclusion on this list, a photo first has to include one of the Simpson sisters in one fashion or another. It doesn’t matter if anyone else can be seen in the background, foreground, or beside them, our only consideration is how attractive Ashlee and Jessica look. Additionally, pictures that are screengrabs of their work in TV or movies are okay; thus, any screengrab of their work is fair game. Finally, we put a premium on photos of them from their “prime,” so current images of them were not in the running. So, without any further ado, let’s get to the list.
20 The Hot Chick
A movie that starred Rob Schneider, an actor that isn’t exactly seen as a luminary in the field, The Hot Chick isn’t seen as a classic film in the hearts of most people. Still, it wasn’t without a few charms of its own, and the biggest of the bunch is the inclusion of a few notable and beloved supporting actresses. If you haven’t seen the movie and are wondering what we are talking about, women like Anna Farris, Rachel McAdams, Melora Hardin, and Ashlee Simpson appeared in the movie. Cast as a cheerleader, Ashlee was surrounded by other hotties throughout and in the scene this image is from. Still able to steal all of our attention, it is simply marvelous to see her in that belly shirt looking positively splendid.
19 2003 American Music Awards
Major awards shows are yearly events that attract loads of celebrities, a group that is abnormally attractive; which means that there is a competition for attention. Already a group that relies heavily on the adoration of the masses to remain steadily employed, it makes perfect sense that people would do what they could to rise above other celebs in these shows. Seen here at the 2003 American Music Awards, if that was Jessica Simpson’s intention when she put on that outfit, she totally succeeded. Wearing a slinky outfit that shines and shimmers while hinting at her cleavage and midriff, we can imagine that all eyes were on her that night no matter who else was around.
18 “Melrose Place” Intimate Scene
A remake of a classic show from the ‘90s that was known for steamy scenes and raunchy storylines, when it was decided to give Melrose Place another go around, they had their work cut out for them. Fortunately for the studio behind the production, they were able to cast Ashlee Simpson who looked incredible at the time and was perfectly willing to set viewers hearts racing. Participating in a s*x scene here, we can’t see any of her naughty bits in all of their glory, but even hinting at that possibility is enough to get us going. After all, she doesn’t appear to be wearing a top here, and that state is one that anyone attracted to women is likely to love—us included.
17 “That ‘70s Show”
A sitcom based in the ‘70s that seemed to come out of nowhere to be an overnight hit, That ‘70s Show featured several women hot enough that people were dying to see more of them. While it was ladies like Mila Kunis, Laura Prepon, and Tanya Roberts who worked each week to bring in viewers, guest stars like Jessica appeared as the series progressed. A part of the fifth season of the show, her character became involved with Ashton Kutcher’s Kelso, and in a move that brought pleasure to millions, the pair was shot sunning themselves supposedly on a beach. Wearing nothing but a bikini and a top that has shifted here, her breasts in a bikini are something that all of us should take in with a smile in our hearts while our pulse races.
16 Natural Cleavage
A picture that clearly seems to be a part of a photo shoot Ashlee took part in, it seems like the design of the resulting images was to capture a more relaxed and natural side to her. The results are proof positive that she is a striking woman that doesn’t rely on a lot of theatrics to look good. After all, there may have been a crew working on capturing this photo but she seems right at home in her own body here. Of course, we’d be lying to you if we tried to pretend that a large part of the appeal of the result of all that work is the amount of flesh on display. Showing off a great deal of cleavage which gives us a great idea of what she was working with, her sister may be the one that is better known for large breasts but it clearly runs in the family.
15 Daisy Dukes
If you were alive when The Dukes of Hazzard aired, you’ll know that it was an absolute sensation. Known all over the world for being a fun and entertaining show that was pretty silly but packed with a lot of fun and action, it seemed like everyone wanted to drive a Dodge Charger because of the show. Another thing that has played a part in the series’ immense popularity was how hot the Duke’s cousin, Daisy, was and how much people loved seeing her in her trademark short jean shorts. Fast-forward to the release of a film adaptation of the series, and it was clear that they needed an alluring woman to play the part who looks amazing in her classic outfit. Fortunately for them and us, we can only kneel before an image like this and pay tribute to how amazing Jessica looks in Daisy Dukes.
14 Cracked Photoshoot
We just touched on a picture of Ashlee from a photo shoot where she looks like she is in her own element; and now, we are going to another one, but the results are vastly different. Looking incredibly made-up, it seems like there isn’t a single hair or wrinkle of clothing that is out of place, and we’re quite certain that a liberal amount of Photoshop was at play here. As a result, you may be wondering how we can enjoy both photos so much, and we hate to admit that it comes down to our base instincts. Yet again revealing a lot of cleavage here, we also get the rare opportunity to see her midriff which is an opportunity we would never happily pass up.
13 Employee Of The Month
Employee of the Month was a 2006 movie focused on a pair of employees of a Costco-style box store doing everything in their power to earn the affections of their new co-worker. Not exactly the most original story in the world, this movie was partially buoyed by the inclusion of Jessica, despite her dubious acting abilities. We say that because we found it totally believable that people would work so hard to win her hand, especially when she makes plain Jane clothes like those look great. Seen here in a shirt that on someone else wouldn’t be remarkable, it is the size of her chest that makes her cleavage such an alluring thing to see, as you can see here, if your mind isn’t overrun with lust.
12 Bubbly Cleavage
A photo taken from the era in which Ashlee was at the height of her music efforts, it makes perfect sense to see her here alongside a bunch of bubbles as her career would burst before too long. A picture that is actually the perfect combination of what we enjoyed so much about the previous two images of her we listed here, this somehow seems contrived and natural at the same time. On the one hand, it seems like she is trying really hard to be an edgy artist with her ample eye makeup and clothing choices. However, the opposite is also true, as the highlight of the photo is her body is on display. And, I mean, what could be more natural than that? This time showing off the most cleavage yet and throwing in some leg for good measure, there is no doubt in our minds the results are hot as hell.
11 Rear View
An extremely beautiful woman to be sure, Jessica has it going on. However, there is one thing about her image that is certain—her chest receives the lion’s share of the attention. While we can’t fault that fact, as there is no doubt that we can’t get enough of her chest either, we find it sad that her derriere isn’t given its due. Fortunately, there is an image like this one where her rear end is front and center and looking really good. On top of that, we love the chance to see her chest from the side and get a glance at her back, as there truly is something intimate about the feeling of appreciating an oft-covered part of someone.
10 Arms In The Air
Now, we get to yet another example of why we like to celebrate the front side of this sexy celebrity too. Seemingly dressed in nothing but a pair of panties and a bra, we aren’t getting a great view of her bottoms here, aside from the tops of them. But, seeing any of them is tantalizing, to say the least. We also have to sit in appreciation of whoever was in charge of her makeup that day as she looks stunning here, and we love having our eyes drawn to her succulent lips any time of the day. That said, the best part of this image in our mind is the view of her chest with her arms raised, which makes them all the more appealing.
9 “Invisible” Music Video
We admit that we haven’t spent much attention to the music career of Ashlee Simpson and principally know of it through some of her embarrassing mishaps. You too are probably aware of when her stadium performance was booed or when she was caught lip-syncing on Saturday Night Live, but it seems like many of us were missing out. That isn’t a reference to her singing ability, which could be awful or amazing for all we know. But instead, it is her music video that we feel we should have paid more attention to. Seen here in a still shot from her clip for the song “Invisible,” she can be seen in a ring ready for a fight and looking awesome. Clearly wearing nothing but a sports bra for a top, she may be trying to look like a total bada*s–something she is barely succeeding at–but we can’t help but take note of her looking sexy instead.
8 Onstage Corset
As much as this list is focused on the looks of Jessica Simpson and her little sister, it shouldn’t be forgotten that she has shown her vocal skills, and she deserves a lot of respect for that many times over the years. Seen on stage here, she is clearly in the midst of a performance for her fans, and it is obvious that she knew that people were likely to love it if she showed off the goods a little bit. Sporting a bright-red corset that provides a lot of cleavage while also tantalizing viewers, the women behind her have huge smiles on their faces. We would too, if we had that view.
7 Knit Top
Clearly at a public event here, we have no idea whatsoever where Ashlee was when wearing this knit top, and we didn’t bother to try and figure that out for even a moment. That is because it doesn’t matter at all, as there are so few situations in life when we wouldn’t celebrate her wearing a barely-there top like this. In fact, if we were at the funeral of a loved one and she showed up in that, we’d have a smile on our faces while those around us reacted in disgust. Able to cover up most of her chest, we still love the fact that we get to see her side boob enough in this image.
6 Lady In Red
The song “Lady in Red” is a classic one for a number of reasons, not the least of which are the lyrics’ ability to make listeners envision a gorgeous woman dressed in the color before their eyes. Don’t worry if your imagination isn’t powerful enough to do that, though. We’ve now provided you with a great image you can draw on whenever the song can be heard in your vicinity. Sporting a sincere-looking smile that draws the viewers in and allows them to see her as someone who seems kind, on top of being hot, the appeal of that enticing smile pales in comparison to her body here. Dressed in a tight dress that shows off her body to a very large degree, the opportunity to see her garment rise and fall with her chest is something totally deserving of celebration.
5 All Wet
There is something that we all seem to know on an instinctual level—hot drenched women greatly appeal to us. Maybe it is because we can picture the liquid invading every inch of their body, and it is thrilling to live vicariously through that. Maybe it is because people often disrobe prior to getting in the shower or wear very little while entering a body of water. Whatever the reason, there is no doubt that it brings about a feeling of great lust and passion in us that we are only too happy to experience. A perfect example of that is this photo. Here, we have Jessica all wet, with her clothes clinging to her body, and it is nearly impossible for it to get better than an image like this.
4 Melrose Place Bikini
We’re just going to say it on behalf of everyone around the world who is attracted to beautiful women. Whoever it was that first designed the bikini deserves a humanitarian award of some sort. A type of clothing that results in the opportunity to see women wearing very little fabric at all, they provide a great opportunity to create fantasy fodder. That being said, this picture of Ashlee from Melrose Place where it is delightful to see her tight stomach, impressive legs, and soft skin, which we can’t get enough of.
3 Melrose Place Bra
Our top pick for a photo of Ashlee, you may be surprised to see which image took this hallowed place. We say that because of the fact that you can’t see any of her from the chest down, and it makes no sense that this picture beat her in a bikini out as we got to see much more of her. So, you may be asking yourself, how does that make any sense? It’s quite simple actually. Despite the fact that there isn’t a practical difference between a bra and bikini top, in reality, there is a huge one. Generally speaking, if you go to any beach, then you’re going to see loads of ladies in bikinis. But, if there is something infinitely more intimate about seeing a woman in her bra, here we are with such a chance to see a lady we like to look at with her bra out while sporting a smile no less.
2 On The “Sweetest Sin” Set
Another image of Jessica Simpson related to one of her music videos, in this case, for the song “Sweetest Sin,” that is very apt as we have a lot of sinful thoughts while looking at her here. Not actually from the video released with the song, instead, we got the opportunity here to see what she looked like on set, and it makes us think about the film crew. We have no idea if the people on the set of this music video were well-paid, but one side of us thinks that they deserve to go home rich for providing the world with a picture like this. However, we also think that maybe they should give it all back since they got to hang out while she looked like that, and getting that show in person is worth more than even a sack of cash. In the end, who cares about any of that while looking at a photo of this bombshell blonde in a state that leaves very little to the imagination like this?
1 These Boots Bikini
The second screengrab of Jessica that is related to her portrayal of Daisy Duke in a film adaptation of The Dukes of Hazzard, here, we see her from a music video she recorded for a song on its soundtrack. Also a remake or cover, as it is called in music, Jessica sang “These Boots Are Made For Walkin’” and while she is a talented singer, viewers of the music video weren’t thinking about that. Instead, we sat in stunned appreciation of the footage of her cavorting around in a bikini. Looking mind-bogglingly hot in a bikini that showed off every bounce of her body, even a still image of her in it is more than enough to be included on this list.