People have been in love with Jessica Simpson ever since she appeared on the scene with her debut album in 1999. She went on to earn millions of dollars not only as a musician but also in other areas such as the world of fashion, film, and of course, reality TV. Though when you consider one of the entries on our list is about a movie that went straight to DVD, you may get the impression that her film career didn't exactly live up to her expectations.
But no matter how bad some of her movies were - which we'll make abundantly clear - we'll also make it clear why many people think she was the most beautiful celebrity in Hollywood. And just in case you don't remember how Jessica Simpson looked throughout the early 2000s, we have some of her best outfits to remind you. Proving just how old some of the photos are, we also have fun "cameos" from various celebrities including Jennifer Love Hewitt, Paris Hilton and Nicole Richie, and even Beyoncé from when she was still in Destiny's Child.
And while it wasn't until 2012 that Simpson found herself eating for 2, the world definitely didn't wait until then to start talking about the fluctuations of her weight. Something that we'll also cover. Including her moment back in 2009 when she hit up the stage wearing what became infamous as her "Mom Jeans" look.
Jessica Simpson is still going strong in 2018 and that will make it even more enjoyable as you sit back and see the 25 Photos Of Jessica Simpson From Before She Had Kids.
25 The Record Executives Shaped Her Image
Jessica Simpson knows firsthand that the image that she put forth to the world is one that has been altered by different executives. This was something that Simpson said was especially apparent when her career was first starting out,
"When I signed a record deal, I was always told by execs I needed to be like everybody else, that I had to show my midriff, things that would take away from who I want to be as an artist. I really want to be just a singer-songwriter. That's who I am."
She probably felt confident in how she looked going into the meeting to sign that contract, which means that the demands of the executives may have been all the harder to take. After all, it must have been hard to finally sign a big deal and immediately get told that you need to start making sure you fit into the "mold" of all the other young pop stars.
You just need to hope that Simpson never found herself in a position where she had to agree to a potential photo shoot that left her feeling uncomfortable about what was asked to say, or perhaps more importantly, wear. Especially because we are sure she felt an incredible amount of pressure to just go along with whatever it was that the record executives were saying.
24 At Her 20th Birthday
Jessica Simpson had plenty of reasons to be ecstatic when the time came for her to turn 20 years old. It was that year, 1999, that she achieved one of the biggest goals of her entire life when her debut album "Sweet Kisses" was released. And what better way than to celebrate by having a birthday party that also features a giant version of what your album cover looked like on a cake. Let's just hope the cake was delicious to eat.
It was reported that when all was said and done that over 4 million people had decided that they wanted to buy a copy of Simpson's music.
Though the fact that one of the singles off of her album,"Where You Are" was a debut with her now ex-husband, Nick Lachey, something tells us she may not be a huge fan of going back and listening to her earlier work.
Unfortunately for Simpson, the next time she released an album was in 2001 and saw a much smaller number in the sales game; selling a little over 500,000 copies. Which means that she probably wasn't interested in having a birthday cake in the future with that album cover!
23 She Auditioned For The Mickey Mouse Club
Jessica Simpson definitely shouldn't have too many complaints about how her life has ended up. But that doesn't mean she hasn't had her fair share of disappointments and roles that she didn't get that she wishes she had.
Did you know that her shot at fame could have been a lot sooner if she had been successful in her audition for The New Mickey Mouse Club? Simpson was only 12 years old when she thought that she had the chops to make it on the show. Which, if you're not familiar, helped start the career of many prominent celebrities such as Justin Timberlake and Ryan Gosling, but also fellow female musicians like Britney Spears and Christina Aguilera.
But when Simpson was later interviewed about why she came up short in her attempts to make it on the show, she revealed that she was intimidated by those two very talented female vocalists (though Justin also probably didn't help her nerves). As a result, she suffered from some stage fright when it came for her time to potentially shine.
We are sure that both Spears and Aguilera are also very glad that Simpson ended up flopping and gave them the opportunity to make it on the show and start their journey to fame.
22 She Doesn't Try Things On In Stores
Jessica Simpson has surely had many outfits that she wishes she didn't end up wearing out in public. But when Jessica Simpson was asked about her shopping habits, she perhaps gave some insight as to why she may have had some less than flattering looks over the years.
"I am not a person who tries on in the stores. It drives me crazy. So I buy and take back if I don't like something. I really don't enjoy being in the dressing room. I rather just try it on in my house."
Though if we're being fair, Jessica Simpson going shopping anywhere is surely going to attract some attention from the paparazzi.
Which means that she may find herself with a lot less time to not only go shopping but also to try on different things. And when you look like Simpson does, you can understand why she may feel pretty confident that she'll look good in most outfits.
Even if that confidence has led to some fashion faux pas. Though if she ever gets seen wearing an outfit out in the world by the paparazzi, that definitely may make it a little bit harder for her to then go and return the item at the store and act like she never wore it.
21 She Loves Her Big Rib Cage
Jessica Simpson has made a name for herself in various industries, including releasing several different musical albums over the course of her career. Which means that you may think that Simpson looks her absolute best when she is up on the stage belting out a high note.
When she was discussing what advantage she has that helps her in the world of singing, she replied,
"I have a huge rib cage, which is why I can hold a note out until I'm blue in the face... because I have such a big lung capacity."
Which you can admit is definitely a positive trait to have. And while her singing career has slowed down as she has gotten older, photos like this from her youth are always going to be fantastic to look at. And considering she hasn't exactly struggled to succeed financially in the world, it's hard to imagine she has too many regrets about how her music career has ended up. Even if there have been some missteps on occasion.
Let's just hope that her husband, Eric Johnson, is a fan of her music. If not, it may become extra awkward at home when she comes on their stereo and he quickly reaches for the skip button.
20 She Felt Innocent At The Start
When Jessica Simpson was first making a name for herself in the industry, everyone out there was trying to put a label on how she was as an artist. When Simpson was asked by an interviewer on how she would define her personality, she replied,
"I think that freshness and that innocence is something that is missing from a lot of female singers. I'm certainly not denying that I'm young, but I'm not fluff," replied Simpson to the interviewer.
Simpson has continued to prove that she "isn't fluff" throughout her career as she has embarked on several successful ventures that show how intelligent she is. Even if one of them was appearing on her own reality show with Nick Lachey, which didn't exactly highlight her smarts.
When Simpson was also asked to define what she thinks the difference is between being dumb and ditzy, both labels that have been applied to Simpson in the past, especially at the early stages of her career, she replied,
"I think there's a difference between ditzy and dumb. Dumb is just not knowing. Ditzy is having the courage to ask!"
She is definitely right about that! And there should definitely be no shame in being comfortable enough to ask a question when you don't know the answer.
19 How She Felt At 25
Jessica Simpson has gone through several ups and downs under the public eye. This includes a divorce from Nick Lachey. But when Jessica Simpson sat down for an interview with W Magazine back in 2006, she was very upfront about how she was feeling about living the single life.
"I just feel alive. I feel free. I feel like I can do anything and there’s nobody to answer to but myself. It’s been hard, but I’ve finally come to the realization that it’s okay to not be perfect. I really am in a comfortable place."
At the time, she was 25 years old. While divorce is definitely something that could be very traumatic and forever alter her in a negative way, her fans were happy to hear that this was how she was feeling after. We would also hope that Simpson feels even more secure in her own sense of self now that she is now 37 years old and no longer has to wonder about who it is she is going to spend the rest of her life with. Though if Simpson did ever find herself single and ready to mingle again, something tells us it probably wouldn't take very long before someone came knocking on her door.
18 Hanging Out With Jennifer Love Hewitt
Jennifer Love Hewitt was one of the most successful celebrities of the late '90s. This included appearing in I Know What You Did Last Summer as well as the sequel, I Still Know What You Did Last Summer that came out in 1997 and 1998. This means that Hewitt was also a fantastic candidate to help volunteer at the US Open's Kids' Day that went on back in 2000.
And what better person to help make people even more excited about tennis, than Jessica Simpson! If we really have to think about it, Jessica Simpson may not exactly be the most comfortable on a tennis court. But they didn't exactly get the nod for the event because of their athletic prowess.
Plus, both of these ladies being willing to volunteer for an event is still a good look on both for both of them. As are the outfits that they just so happened to pick out for the day. And while Jessica Simpson doesn't seem to have much of an interest in returning to the world of television/film anytime soon, that isn't the case for Jennifer Love Hewitt. It was announced earlier this year that she is going to be playing a central role on the new hit drama 9-1-1 that is going to be entering its 2nd season.
17 She Was Straight To DVD With Private Valentine
We are sure there were many moments in Jessica Simpson's acting career where she was perhaps not too sure if there was a future for her in the business. But if there was ever a nail in the coffin, it may have been when in 2008 she appeared in the comedy Private Valentine: Blonde & Dangerous. The film follows an actress who finds herself struggling and as a result, decides to join the army.
We don't really know what Simpson would have been thinking when she agreed to sign on to the film. But when the project ended up being skipped over by theaters in North America and instead was released straight to DVD, we wouldn't blame her if it left her thinking she needed to hire a new agent. Because there is no way that signing on for a project like this did any good for her career and took up what was probably some crucial time during one of her biggest peaks.
If there is any positive that comes from the film, it may be that you get to see what Simpson looks like in an army uniform. Though that probably isn't enough to justify you going through the trouble of actually tracking down a copy of the movie and dedicating your night to watching it.
16 Her and Nick On Newlyweds
Jessica Simpson and Nick Lachey's time in the spotlight was at one point best defined by their time on their reality show Newlyweds: Nick and Jessica that ended up lasting for 41 episodes.
But a producer from the show has been very open about the amount of tension that was often present during filming,
"You could feel there was tension between the two of them. They were very different people. He was a blue-collar guy—he did a lot of things himself, like he and his brother would build things. He was frugal, and she had excessive taste. In the end they weren't suited for each other."
The producer didn't stop there, as he went on to say
"The only thing they really had in common was their music. She was really young; I think he's seven years older than her. He wanted a family, and her father thought maybe she was too young. Her father was very involved in her life. "
Though it may make you feel better to hear that when Jessica was asked about the show, she said,
"I'm happy I did the show. I'm happy I was married. I'm happy that he was in my life. I have no regrets. And I will look you in the eye and tell you that I have no regrets about that. Not one."
15 At The Vanity Fair Oscar Party
Eric Johnson definitely had to know he was a lucky guy when he was able to get Jessica Simpson to marry him. Especially because if we're being honest, his career in the NFL definitely didn't have anything flashy about it as he was drafted in the 7th round, battled injuries and scored 9 TD's over the course of his career that went from 2001-2007.
This photo was taken from 2010 which was the same year that he decided to go down on one knee. When Simpson was later asked about the proposal, she replied,
"I actually had to sit on his knee I was so shocked...to really get what was happening. I said 'Yes' and we both definitely were teary-eyed. I didn't even try the ring on until like, five minutes in. I just kind of sat there and cried with him."
She also had plenty of praise for Johnson, saying,
"He's just really thoughtful and he keeps me very centered and always makes me feel like my feet are on the ground. He's probably the most special part of my life."
While the two went on two have two children together before they eventually took that walk down the aisle, we're sure that doesn't make his proposal any less sweet.
14 Jessica With Paris and Nicole
Jessica Simpson was one of the biggest stars of the early 2000s, but she wasn't the only blonde bombshell to make a name for herself during this decade. And just in case you need your memory jogged, this photo can serve as a reminder of two other ladies who became famous during this time period. Paris Hilton and Nicole Richie.
Both of whom skyrocketed to fame due to their reality show The Simple Life which came out in 2003 and lasted until 2007. Considering Simpson's career was also helped by her reality show Newlyweds: Nick and Jessica, we are sure the 3 ladies had plenty of relatable stories. Though if you want the whole picture about the fame of Paris Hilton, she also owes part of her popularity in society to the fact that she was involved in a scandal surrounding the leak of her intimate activities with Rick Salomon. Something that was definitely more real than anything that ever went on during The Simple Life.
We are sure that Jessica Simpson is incredibly grateful that while she has had various scandals in her career, that she has always managed to be able to stay clear of any scandal involving intimate activities.
13 She Was On That '70s Show
Danny Masterson was the face of ugly headlines when rape allegations were made against him back in 2017. But putting that aside, That '70s Show was still a show that benefitted greatly from the chemistry of the main cast.
That being said, that '70s Show also had many fantastic guest stars that helped play a role in the success of the series. Such as Alyson Hannigan who joins the series at one point and pines after Ashton Kutcher's character, Kelso. But she's not the only guest star who has tried to get all up on the business of Kelso. One who was far more successful in her goals was Jessica Simpson, who played the role of Annette for three episodes back in season 5.
While we're sure she wouldn't have minded getting the opportunity to stick around for longer, it was still a great opportunity for her to try and advance her career further. Though unfortunately for Simpson, it ended up being the only significant time she ever landed a role in a television show.
We hope that isn't due to the fact that working on That '70s Show was a bad experience and more that she realized that there were more productive things she could do with her time then trying to make it in the world of acting.
12 She Dated Tony Romo From 2007-2009
Jessica Simpson had a high-profile relationship with Tony Romo that started around Thanksgiving 2007 and ended back in 2009. When Skip Bayless was asked to weigh in on the potential ramifications that the relationship had on Tony, he replied that Simpson almost ended his entire career,
“He had to pay too much attention off-the-field and he was not dedicating himself to the process of playing NFL quarterback.”
Though to be fair, when they were dating, Tony did say,
"She comes to a ton of games. She’s a supportive girlfriend.”
Which means it may be easier to believe that Simpson did everything she could to try and support Tony. And to be fair, it seems pretty ridiculous to blame her for the numerous problems that have plagued the Dallas Cowboys. Though the following year, Tony did post what ended up being one of the statistically best seasons of his career. Which means that at the very least, he may not have been hurting too much from their separation.
When you consider the fact that many of the photos on our list are from 2007-2009, you can also assume that Simpson was ending that day by getting to go home to Tony.
11 Jessica and Beyoncé In 2000
Jessica Simpson must have felt on top of the world back in 2000. It was in 1999 that her first musical album was released and she was definitely one of the most talked about names at the MTV VMA's back in 2000. Even if she wasn't able to come home with any awards. We're sure it didn't damper her mood too much though. And if it did, you definitely can't tell from this photo. And while Simpson may look fantastic in this photo, we still wouldn't blame you if your eyes immediately went to Beyoncé who is standing to her left.
Because let's be honest, Jessica Simpson is an amazing superstar, but there is really only one queen! And we are sure Simpson would not be shy to admit that her musical career definitely didn't reach the same heights as Beyoncé's did. And we're sure if you told both of these ladies what the next decade of their lives ended up looking like that they would have been incredibly surprised. Though hopefully pleased with how things turned out!
Though you may think that Beyoncé looks a lot better in 2018 than she did back in 2000 when she was still working with the girl group, Destiny's Child.
10 Increasing Your Interest In Christmas
There are many tremendous Holidays that are always fun to celebrate. But if we had to guess as to what Holiday is the most beloved by people, it may have to Christmas. Which is really more like an entire season for some people than any Holiday. This love for Christmas is especially apparent for some musicians who take their love of music to the recording studio.
This was the case for Jessica Simpson, who in the past recorded "ReJoyce: The Christmas Album" which came out in 2004. Which you have to imagine still gets some playtime around the Simpson household. The album also helped raise her awareness even more for when she appeared in The Dukes of Hazzard the following year.
Perhaps part of why Jessica loves Christmas as it is partially responsible for how she first met Nick Lachey, as they were at a Christmas party. And while they later divorced, she still loved him deeply at one time.
While we don't know what Eric Johnson is going to be getting Jessica this upcoming Christmas, if she is running around in the middle of December and scrambling on what she should get him, maybe she can just agree to wear this outfit around the house! Something tells us it's definitely not a gift that he would forget anytime soon.
9 She Was In Dukes Of Hazzard
Jessica Simpson has had many moments in her life where you may think she looks her best. But if there was even an emphatic moment in her career that stands out to most people, it's when she agreed to take to the big screen with the film The Dukes of Hazzard. A role that also required Simpson to show off plenty of herself to the audience.
When talking about her reaction to having to display her body in the movie and the training regimen she underwent, she replied,
"Immediately when I found out that I had the part I was like, 'OK, this is it.' It's the best to be able to have something to work towards, otherwise I'll stick to fried food and Taco Bell. But to have a goal is awesome. So I ate my last piece of chocolate cake when I found out, and ever since I've tried to cut sugar out of my diet, except fruit. But pretty much I just eat health and I work out close to two hours every day."
Simpson also went on to describe that she had an influence in the wardrobe,
"Yeah, oh my god! You can't even imagine how many pants and jeans I tried on for this movie. Most of them were jeans that we just cut off and made them as short as we wanted to, which is more than probably I would wear them."
8 She'll Never Drop Her Clothes To The Floor
Jessica Simpson has definitely stepped out for a night on the town wearing outfits that many people would consider to be revealing. Though to be fair when you consider how many people have desired after her, perhaps that helps fuel into her overall sense of confidence and her belief that she can pull off any outfit. She has also been asked to leave little to the imagination with some of her roles in movies and television shows in the past.
But when Jessica Simpson was asked on if she would ever drop the clothes entirely, she was adamant that it wasn't going to happen,
"I don't care how dark and intellectual the role could be, you know. I don't care if I frickin' could get an Oscar for it, I'm not going to do it. Those accolades mean nothing to me. I don't think people deserve to see what's under my clothing."
When you consider the fact that Jessica Simpson is currently seemingly content with not continuing her movie career, with her last project being in 2014, you can also be sure that this isn't an opinion that is going to change anytime soon. Especially because that also means that no Oscar roles are probably coming her way.
7 She Was In Employee Of The Month
Jessica Simpson, Dane Cook, and Dax Shepard came together in 2006 to make the film Employee of the Month. When it came to critics, they definitely were not a huge fan of the film. According to Rotten Tomatoes, it came away with a score of only 20%.
But on a more positive note, the film did manage to do pretty well at the box office. While it had a budget of $12 million, it managed to make close to $40 million at the box office.
When asked what the dumbest thing Simpson said on set, as she had a bit of a reputation for being a bit of an airhead, Dane Cook replied,
"I think she said one day, 'Are we making a movie?!'"
If she was ever confused about what was going on, on set, you can perhaps get a better understanding as to why the movie didn't do so well with critics! Though if it's any consolation, Simpson definitely still looks great in the film. But there is more to being a successful actress in Hollywood than just looking beautiful on the big screen. We are sure that if Simpson was asked about that quote that she would probably end up denying it.
6 Nick's Glad They Didn't Have Kids
A big part of Jessica Simpson's life before she had kids was spent being in a relationship with Nick Lachey who she agreed to marry in 2002. But things didn't end up working out for the two of them and they eventually decided to go their separate ways in 2005. Which may explain his answer, as when Lachey was asked to reflect on his relationship back in 2014, he replied,
"I think in our situation, that was probably the best thing that could have ever happened is that we didn't have kids. All things being equal, it was the best thing probably for the both of us that we went on with our lives and she's obviously happily married with two [kids]. I'm happily married about to have two so it all worked out the way it was supposed to work out."
Lachey has been married to Vanessa Minnillo since 2011. Their relationship has obviously continued to go well as while he was about to have his 2nd kid at the time of this interview, they've since gone on to also add a 3rd one to the party. We are sure that if Simpson was asked the same question that she would also agree that she was probably not at the right stage of her life to have a child with Lachey. Take this as a win for using the proper preventative methods in the bedroom!
5 Her "Weight Gain" Was 10 Pounds
Jessica Simpson is definitely comfortable letting the world know what she looks like on a regular basis due to her Instagram account. But before social media, if the general public was asked about how Jessica Simpson looked before children, she admitted that the public perception at times was still that she was very overweight. Even when that really wasn't the case.
“People wouldn’t stop talking about my weight for an entire year. The fact that I was famous for gaining 10 pounds last year is ridiculous...People really think that I’m 245 pounds. It’s really a hard thing for me to talk about because I celebrate women of all sizes.”
We are sure there are many people out there who can relate to their weight fluctuating like that. Simpson also admitted that part of the reason as to why she feels she was so scrutinized for her body during this time in her life was because she appeared on the MTV reality show Newlyweds: Nick and Jessica.
"I do think that I opened myself up to the world to judgment, people’s opinions. In a lot of my ways, it was my fault."
Though being on a reality show definitely doesn't open her up to the level of abuse that we're sure Simpson has had to endure throughout her career.
4 Sitting On a Swing For a Photoshoot In 2000
If we are being completely honest, we don't exactly know what is going on with this photo. But there is no question that it is at the very least entertaining. And while Jessica Simpson may not be showing off the most skin, that doesn't detract from how beautiful she looks. Even if the idea of having her sit down on the swing and pose for the camera is one that may raise some eyebrows.
This photo was definitely taken long before Jessica Simpson thought about having kids, though her decision to drape her hand over her stomach would be one that we wouldn't be shocked if it had the paparazzi guessing! The idea for the photo shoot was brought about by Stephen Danelian and was done in 2000.
And just in case it made Simpson feel even more relaxed, her partner at the time, Nick Lachey also joined in for a few of the photos. Though we wouldn't be surprised if when they later got married in 2002 if they definitely didn't want to include any photos of Simpson sitting on a swing. Considering the two are also now divorced, we're also sure this isn't a photo that would bring on too many fond memories for either Simpson or Lachey.
3 People Also Thought She Looked Heavy With Eric
Jessica Simpson got engaged to Eric Johnson in 2010 and it wasn't until 2012 that they decided to have their first child. Which means that there is a time period where Simpson and Johnson would go out and have the tabloid media tag along for the date.
And when talking about the controversy around her weight gain at times, she also referred back to a time period of her relationship with Eric where she may have been at some of her heaviest weight and how he made her feel
“I’d been scrutinized about my weight before I got pregnant, so I refused to let anyone steal the joy of my babies. My husband and I were looking at old pictures recently, and I asked him, ‘Babe, why didn’t you tell me to put the brownie down?’ He said, ‘You looked great.’ He’s always loved every curve on my body.”
That is definitely the kind of support that a partner needs to have. Especially if that partner just happens to be Jessica Simpson who is always going to find herself at the source of criticism, but will be able to shake it off a lot more when she has Eric telling her she's beautiful.
2 The Infamous Mom Jeans From 2009
There are many photos on this list that make it abundantly clear just how good looking Jessica Simpson is and why so many people love her. But one of the worst moments of Jessica's life came when she elected to take to the stage wearing the outfit that we have featured for you above.
It wasn't long before the photos went viral as the world dubbed her wearing "Mom jeans". Keep in mind that this happened was back in 2009, which was still years before Simpson had her first child. Simpson was also criticized for apparently looking heavier than usual on this particular day.
If you're in agreeance that she definitely doesn't look overweight, then perhaps you'll also agree that it's ridiculous the level of standards that the tabloid media holds over these celebrities. When Simpson was later asked about the incident and the backlash that she received from wearing this outfit, she replied,
"I would not wish on my worst enemy what I went through."
You need to hope that the situation helped her develop a thicker skin when it comes to her critics. But nobody would also blame her if the razzing from the incident made her hate the paparazzi all the more.
1 Her Most Iconic Photo Ever
We are sure that there were many moments in Jessica Simpsons' career where she felt like she was going to hit rock bottom and that she was one of the ugliest people in the world. But as we end this list, we decided to pick one of the most iconic photos in her career. Even more importantly, it's perhaps only fitting to leave you with the knowledge that things have perhaps never been going better for Simpson. Who has been very open in the past about how much she loves Eric Johnson.
And when you know that this is the man that she is getting to spend every night with, you may be in agreeance that her life is going to do nothing but improve until the day she passes away. Simpson has also been open about the fact that while she and Eric love their two children, that they've taken preventative measures to make sure their family does not gain another addition,
"I have two beautiful children and I’m not having a third. They’re too cute! You can’t top that.”
While it's always possible that opinion may change, we're sure nobody would blame them if they're content to continue living the life they are.
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