15 Jessica Simpson Pics From When She Was In Her Prime

Coming from a fairly unremarkable, middle class background, Jessica Simpson is a great show business story of how just about anyone can end up worth an estimated net worth of $150 million. That's righ

Coming from a fairly unremarkable, middle class background, Jessica Simpson is a great show business story of how just about anyone can end up worth an estimated net worth of $150 million. That's right, the sexy blonde who got famous looking cute and singing pop songs in the late 1990s and early 2000s is worth somewhere around that. Of course, she had everything necessary to make it happen. She had a solid support structure, some definite talent and the kind of face-body combination that could be marketed.

There's no question, while she's not a complete dud in terms of songwriting, singing and performing (okay it's pop music, so it sucks, but her voice was decent), if she didn't look the way she looks, she wouldn't have made it as high up as she did. The eyes, the smile, and of course the body were virtually flawless. Now in her mid 30s, Simpson is still looking good, but two marriages and a pair of kids later, she doesn't look like she did at 19, that's for sure.

A couple of years ago she put on some weight (in her defense, she had just had a kid and didn't look bad considering what the tabloids and trolls were saying) but kids and just aging in general have taken their toll. But of course, we'll never forget the good ol' days when she was every man's dream girl and one of the sexiest women in show business. We're happy to bring you fifteen pictures of this beautiful woman back when she was in her prime.

15 You're Missing Some Shirt, But It's Cool

We're not sure what happened to that shirt. There are a few possibilities, though: maybe she was attacked by a jungle cat on the way to this shoot. Perhaps this was actually workout attire (the shorts look like they might be gym shorts) and her top got caught in an exercise machine. We're willing to bet, however, that this picture was snapped back in the early or mid 2000s when that trend of paying extra for ripped clothing was what all the cool kids were doing. No matter what the cause, she looked fantastic, showing off her incredible figure and smoking hot eyes.

14 Those Legs

This was back in 2006 when she was celebrating the release of her album A Public Affair. Jessica Simpson isn't one of the taller, more statue-looking ladies in show business, but still, standing just about 5'3, she had an unbelievable set of toned legs. There really aren't many pictures out there that show off this fact much better. In fact, if that dress got any shorter, we would likely not be able to show this shot at all. Thankfully though, it shows off just enough but not too much (walking a very fine line) demonstrating toned, slim legs that are something special and definitely worth talking about.

13 Irresistible

Back in April 2001, the former Yugoslavian President Slobodan Milosevic was arrested prior to his trial for brutal war crimes, and the Netherlands legalized gay marriage. More importantly though (not really, but for our purposes...) Jessica Simpson's single Irresistible was officially released. The album of the same name was released a month later. Both the single and the album were nothing special, and if you're reading this, we're willing to assume that you're not a fan of her music so you could care less about anything other than the dolled-up stunner on the cover of the track.

12 Daisy Duke

The Dukes of Hazzard took place in Georgia, and obviously Warner Bros. were looking for a sexy southern gal to play Daisy, and had to look no further than this hottie. She looked fantastic in those shorts and actually in everything she wore in that film. Come to think of it, she may have been the only good thing about the movie. The star-studded cast including then-Jackass creator/star Johnny Knoxville, Sean William Scott, Burt Reynolds and a few others weren't bad, but the movie was. A rare miss for Broken Lizard's Jay Chandrasekhar, whose other works include the wacky classic Super Troopers and the catastrophically underrated The Slammin' Salmon. 

But back to what matters, and one thing you should take away from this list: Jessica Simpson looked fantastic in movies and television.

11 Troop Support

If you had to name a celebrity that best embodies what an "American girl" is, it might be Jessica Simpson. Okay, we should clarify, if you like the United States and think of an American girl as blonde, sexy, sweet, classy and just a bit innocent, then that's her to a tee. Of course, if you're not a fan of the U.S. of A, then your picture of an all-American woman might be a 250 lb hog, sitting on a couch, yelling at Dr. Phil on an old TV while wolfing down a quarter-pounder.

But back to the issue at hand, if you're a star from the Southern States, there is no way to endear yourself to your people quite like wearing a Stars and Stripes bikini with some Camo pants. Don't step on the flag or burn it, but by all means, use it to cover your privates, that's always cool.

10 We Couldn't Live Without Cleavage

This is a look that many women cannot pull off and would not even dare to try. We aren't talking about the hair (although a bit shorter looks nice and is outside of her usual routine) or the earrings, nor are we talking about the makeup or the white blazer, but of course, we're not complaining about either. We're talking about the decision to leave the bra at home and let the twins air out a bit. It's daring, awesome, looks fantastic, and of course: it's really, really sexy. Bras help to keep boobs high and looking perky, but in Jessica's case, she didn't need much help in that department (for obvious reasons).

9 Nice... Everything

Now we don't want to go out on a limb here, but that dress she's wearing looks a little like something a lady would wear to bed, but everything else about the picture looks like it took hours to put together.What are you trying to pull here, Jessica?

The straight hair, dark eyes and of course the shoulders, legs, cleavage and all the rest look fantastic, but this is an absurdly beautiful picture. We actually don't know where this picture is from, but when you're looking at something like this, does it really even matter? We'll go with no.

8 Small Red Dress Is Fine By Us

Here, in her natural habitat, we see the magnificent Jessica Simpson looking out of this world. This may well be what a real Goddess looks like. Not one of the Charlie Sheen "Goddesses" though, because those "Goddesses" were a totally different breed who just liked having access to an unending sea of cocaine, and while those model/adult actresses participated in a memorable show business mess, Jessica Simpson looks like a different type of deity in this picture. Just her smile alone is enough to prove why Jessica Simpson was one of the hottest celebrities in her prime. The red dress is just the cherry on top. And we like the cherry.

7 That Carpet Is Living The Dream

This is a monumentally unappreciated look on a woman. It's really nothing special to the untrained eye, and looks like a girl who just rolled out of bed, and wound up on the floor. Now she's giggling, and still on the floor and just enjoying how silly she looks. This is obviously just a photoshoot for MTV, regardless, the whole "panties and an undersized t-shirt" look is a good one and looks really sexy on a woman who is as fit as Jessica Simpson is. You see some curves, a really cute smile, and the fact that she's playing with her slightly messy looking (but likely made to look that way) hair is just the icing on the already very hot cake.

6 One Daisy Duke Shot Wasn't Enough


We have to start this entry off with one, simple word: wow. Just wow. There is not much else to say about this photo. We all know that Daisy works as a waitress, and this is the kind of look and outfit that would garner a large tip from even the stingiest and most demanding of customers. For the 2005 film, the crew really sexed up Daisy (shorter shorts, more boob, less shirt, and so on), and we're fine with that. As stunning as she looks, the expression on her face does not look too pleasant, as if her already demanding customer has asked for a gluten free, vegan item that isn't even on the menu.

5 Showing Off Some Leg

Looking at this shot, we are imagining walking into a room with Jessica Simpson reclined on a couch like this and hearing her say, "hey big guy, how about giving a lady an upper-thigh massage?" While our fantasy would end one way (a good way), most dudes would probably start drooling, babble for a second (or maybe more like an entire minute) and then just pass out in such a set of circumstances. The dress she is wearing is really nothing special, but it does show off a great amount of leg (and as we've said in previous entries, Jessica Simpson has got a sexy set of legs). The high heel boots along with the hair and the sexy look on her face also look like something out of a dream.

4 Hey, You With The Camera, Back Up A Few Feet!

This was the cover of Jessica Simpson's first studio album Sweet Kisses. We can think of some things we'd like her to do to us, but they aren't kisses and there would be nothing sweet about any of it (not even close). This is some of the most shameless and outstanding sexualization of a 19 year old woman we've ever seen by the music business of the late 1990s. She's done up like some kind of perfection and we can't see any clothes so we just have to assume that she's completely naked (likely more or less totally clothed but showing off shoulders and wearing a strapless bra). But no matter what she is actually wearing, the imagination is a powerful thing and we use ours to its full potential with this picture. We know you do too.

3 That's a Nice Dress... But It Would Look Better On The Floor

To be honest, most dresses worn by decent looking women would look better on the floor. Many people don't realize (it's shocking, we know) that the woman makes the dress, not the other way around. You could dress Jessica Simpson in a tarp covered in dirt and she'd still look like a ten. This was at the Met Gala in 2001: the theme was Jacqueline Kennedy: The White House Years. We doubt anyone would have shown up in a pink suit covered in blood, but that would have been tastelessly fitting.

Yes, that's a joke about the wife of a President who was killed in office. Get over it.

But moving away from potentially treasonous (I'm Canadian, come get me) jokes, this dress and the woman underneath it are just fantastic together.

2 Short Hair

Much like her picture from the cover of Sweet Kisses, this great shot leaves much of what she's wearing up to the mind of the viewer. But even if you don't bother imagining what all the bits and pieces look like, her face, shoulders and top of her chest are phenomenal all on their own. This pic gives us a great close up look at her magnificent face, which features brilliant eyes, pouty lips (almost a natural duckface, without looking like an idiot), and an intense sexiness one would expect from a preacher's daughter. Yes, you read that right, her dad is a minister, and yes, we think that makes her a bit sexier (no, we don't think she waited until marriage). Next question please.

1 Nobody Get That Woman A Towel

We repeat: nobody should, by any means, hand a woman a towel if she looks this sexy while soaking wet. Okay, if she's accidentally fallen into a semi-frozen river, give her a towel, but if her health isn't in question, leave her be and watch the clothes cling to the body and check out what's getting hard.

Keep in mind that this was the kind of the thing Tony Romo and Nick Lachey used to get to see whenever they wanted. It really makes you think about the things some men walk away from. We're still not exactly sure what makes a soaked woman so sexy, but we're also not spending too much time worrying about that. We actually wanted to end this article with a sexy picture of her and her sister Ashlee, but no pictures of the two of them were particularly hot, and most definitely nowhere near this one.

Sources:  Yahoo, Biography, IMDB

Give TheRichest a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheRichest?

Get Your Free Access Now!

More in Entertainment

15 Jessica Simpson Pics From When She Was In Her Prime