The up and down transformation of Jessica Simpson


A rocky road

Most of us struggle with our weight, and that goes double for women. Celebrities, meanwhile, spend their lives in the public eye, and are constantly being judged – not just for their talent, but also for their appearance. Singer Jessica Simpson, for example, has been front and center publicly since she was a teenager, and we’ve watched her grow up and mature. However, her road has been far from easy, as she’s often been judged harshly by the media for how she looked, causing her to completely transform her appearance.

Starting out young

Jessica Simpson’s life has been full of ups and downs. From selling millions of albums to getting dropped by record labels, the star has had to fight a lot throughout her career, but she’s never given up. It all started when she was 11 and hopeful of making it big as a singer. After nearly starring on the variety series “The Mickey Mouse Club” and getting close to releasing a Christian album, Simpson finally struck lucky when she was signed to Columbia Records by Tommy Mottola.

Standing out from the crowd

The label saw a lot of promise in Simpson and hoped she would prove worthy competition against growing artists like Britney Spears and Christina Aguilera. While those girls weren’t afraid to appear promiscuous to sell records, Columbia wanted Simpson to have a safer image that listeners could relate to. They hoped that with many other female singers using their bodies as tools for their music, Simpson would stand out from the crowd and go on to sell millions. Whether or not that would work all depended on her debut album.

Not good enough

Although it only peaked at 25 on the Billboard 200, the singer’s debut was far from a failure. The album, “Sweet Kisses,” went on to sell two million units in the U.S., ultimately doubling that total in worldwide sale. Four million copies is an excellent start for someone taking their first steps in the music industry, but it wasn’t good enough for Columbia records. They expected her sales to be stronger, especially with artists like Britney Spears shifting 25 million units for their debut effort. Something had to change.

Changing her image

Despite what they’d asked of her previously, Columbia now wanted Simpson to follow in the footsteps of her contemporaries. The buttoned-up image clearly wasn’t enough to sell music, so they asked her to become more mature in both her look and lyrical content. “Irresistible,” the follow-up to “Sweet Kisses,” was released in 2001 and showed off a more adult side of Simpson. However, it didn’t have the desired effect. While the album did peak within the top 10 of the U.S. charts, its worldwide sales were only two million.

Doing it for the fame

Many of Simpson’s fans weren’t impressed by the change in her image. They felt that she’d sold out to the label in the hopes of becoming rich and famous, and it had all blown back in her face. Rather than helping her to emulate the success of rising stars like Britney, it had just delivered a devastating blow to her popularity. Luckily, although her sophomore album had hurt her career, Simpson wasn’t down and out yet. The label was determined to make a success of her, no matter what.

Waiting until marriage

Although Simpson had distanced herself from her formerly conservative image, she hadn’t completely changed her ways. When she’d been working on her debut album, she’d announced her intention to remain chaste until she tied the knot. That was something that she stayed devoted to until she walked down the aisle with beau Nick Lachey. The two wed in October 2002 and saw the formation of one of pop culture’s most memorable marriages. People were so crazy about the couple that the pair were even awarded their own TV show.

Path to stardom

Titled “Newlyweds: Nick and Jessica,” the series followed the duo around as Simpson worked on her third album. The show was her father’s idea for maintaining her popularity after her single “Sweetest Sin” was a commercial failure. With her career starting to take a nosedive, Simpson desperately needed the reality show to succeed because she was running out of options. Luckily, viewers saw the appeal of the series, and her third album became her most successful yet. It hit number two in the charts and sold seven million copies worldwide.

The next big thing

Having her own show was the best thing that Simpson could have done. The star saw her popularity soar, and there was no sign of it dropping anytime soon. The singer was receiving deals for a cosmetics line, clothing line, and even being asked to perform at the Super Bowl halftime show. People loved the ‘ditzy blonde’ personality that she showcased on the series, and it made them fall in love with her. Unfortunately, what goes up must go down, and trouble was brewing on the horizon.

Coming to an end

Although her marriage to Nick Lachey had helped her achieve phenomenal success, it was a relationship that wasn’t meant to be. At the end of 2005, the couple announced they were separating, with the pair finalizing their divorce in the June of the following year. The split was a painful one for Simpson, but not just because she was losing her husband. She was forced to pay out $12 million in the settlement, leading the singer to refer to her marriage as her “biggest financial mistake.”

The Dukes of Hazzard

There was a light at the end of the tunnel, though. Although her relationship with Lachey dissolved, she wasn’t about to disappear off the radar. Before their split, Simpson featured as Daisy Duke in the comedy film “The Dukes of Hazzard.” The movie further emphasized just how much the star’s image had changed since her debut, with her character notorious for wearing tiny, denim shorts. For several years after the film’s release, Simpson continued to appear as Daisy Duke in various commercials, keeping herself firmly in the public eye.

Causing controversy

Simpson’s penchant for wearing more revealing clothing might have helped her sell records, but it also caused a lot of controversy. Most notably, people took offense to the way she dressed and acted in her video for “These Boots Are Made For Walkin’.” A Christian group said she should be ashamed of herself and demanded she alter the video to something more appropriate. Given Simpson’s upbringing in a Christian family, the group felt she was supposed to be a role model to kids who were once in her position.

Center of attention

Starring as Daisy Duke did a lot for Simpson’s image, with the star appearing in Maxim’s Hot 100 list for several years after the film’s release. She was no longer the conservative girl that people had known her as back when she was growing up, but Simpson wasn’t upset about that. She felt comfortable in her skin, and she appreciated the level of success that she was getting. Her music career mattered to her more than anything, and this new image was helping to take it to exciting new places.

Having the tables turned

Unfortunately, Simpson soon discovered just how damaging it can be when the media focus on your looks. After putting on a little bit of weight in 2007, people started taking notice of the changes in her body. Rather than commending her for being slim, they were suggesting that she’d let herself go. This came as a shock to the star given she was still a perfectly healthy size, and things only grew worse. The media began to crucify her for putting on some weight, and it affected her badly.

An ‘unflattering’ outfit

Everything came to a head when Simpson was accused of wearing an “unflattering’” outfit during a concert in 2009. After several years of people putting her down for the changes in her body, the star decided that enough was enough. She had no reason to feel bad about the way that she looked, and stated that she felt “confident” in her figure. However, the constant criticism made her very conscious about her size, and it planted the fear in her mind that she’d one day gain too much weight.

Defending her sister

Simpson wasn’t alone throughout all this, though. After the comments were made about her “unflattering” look, the star’s younger sister spoke out on the matter. Ashlee, who owed her big break to Jessica’s reality series, was disgusted that her sister’s weight was considered news given everything else going on in the world. She stated that “all women come in different shapes, sizes and forms,” and that being a celebrity didn’t mean that Jessica deserved to be seen through a different lens. There was nothing wrong with her size.

After Defending her sister

Ashlee knew what she was talking about when it came to struggling with your weight, although hers was quite the opposite problem. At 11 years old, she became the youngest child to ever be accepted into the prestigious School of American Ballet in New York City. She found it extremely hard to make it in the ultra-competitive world of ballet, and so struggled with an eating disorder, anorexia, for six months. She got through it, however, with help from her family – and was possibly now returning the favor.

Losing the crowd

The controversy around Simpson’s weight coincided with the star’s move into country music. Her sixth album, “Do You Know,” was her attempt at crossing over into a new genre, but it didn’t receive the best reception from critics and fans. Although the release charted at four on the Billboard 200, it received relatively low scores in reviews. The singer was even booed by a crowd when she performed some of her songs back in 2009. This was one experiment that Simpson’s career could likely have done without.

The price of beauty

Considering all the talk that had surrounded her weight, Simpson was prompted to appear in a new reality series that looked into perceptions of beauty around the world. She traveled to countries like Thailand, Morocco, and Japan to explore how the people there express themselves through fashion and beauty regimes. “The Price of Beauty” marked a welcome return to the genre that had made Simpson a star, and it sent out an important message to everyone watching at home. Even if we all look and act differently, we’re still beautiful.

Shopping for diets

The first diet Simpson ever tried out was the famous Atkins diet, the controversial low-carbohydrate weight loss fad named after physician Robert Atkins that has the dieter eat mostly eggs, meat, and cheese. While initially succeeding to shed pounds, Simpsons later found it “really messed (her) up mentally,” while also causing her to feel bloated. She later gained back all the weight she’d lost, but found a new approach in the process – and a new outlook on life to boot.

‘Curves are in’

After discarding the Atkins diet, Simpson formulated her own far less severe eating plan, which helped her stay at a healthy weight for a woman her age. As is often the case, this newfound stability in weight also got her a new lease on life. Her entire perspective had shifted, and she learned to accept herself for who she was. “I feel like curves are in,” she said. “They make your outfit look better, and I like having something to pinch.” You and us both, sister.

A new blessing

Shortly after The Price of Beauty aired on MTV, Simpson started up a relationship with former NFL player Eric Johnson. Within a matter of months, the two got engaged, eventually tying the knot in 2014. Before they became husband and wife, though, the pair welcomed two children into the world. Their daughter, Maxwell, was born in May 2012, while their son, Ace, followed in June 2013. Simpson’s size once again became a topic in the media given the pregnancy weight she put on, and it pushed her to make a big decision.

Going to extremes

While she was pregnant with baby girl Maxwell, Simpson said her weight had reached an all-time high – 170 pounds! After the birth, she was itching to shed all that weight, and may have gone to a solution most of us would consider to be extreme. Simpson went on a diet that had her drinking nothing but smoothies for a full 15 days! “Being pregnant for two years took a toll,” she told USA Today, and apparently wasn’t kidding about reversing the situation.

‘Is this chicken…’

Somehow, and you knew this was coming, Simpson’s most iconic food-related moment had nothing to do with her weight. In a Newlyweds episode, she and then-husband Nick were having dinner when she stopped, contemplated, and asked, “Is this chicken, or is this fish? I know it’s tuna, but it says ‘Chicken of the Sea.’” A perplexed Nick could only stare. Last year, retailer Whole Foods got into trouble for having tuna in their chicken salads. Simpson tweeted a screenshot of the story and added, “It happens to the best of us.”

Denying dumbness

On top of her most infamous moment, Simpson once gave a performance in 2009 in which she forgot the lyrics to one of her songs. She decided to perform another one instead, only to forget the lyrics to the second song as well. Ouch. Nevertheless, she vehemently denies the “dumb blonde” label she’s been saddled with. She did admit to being ditzy and clumsy, saying, “I will walk into a room and fall on my face.” But stressed in no uncertain terms: “I’m not dumb.” She certainly has some weird habits, though.

Curious personal habits

In a 2010 interview with Ellen DeGeneres on her successful talk show, Simpson revealed she only brushed her teeth around three times a week. Yikes. What’d she do on those other days? Used a T-shirt to wipe them down, naturally, as she said she didn’t like it when they felt slippery. Her rationale for doing so was pretty ironclad. She reasoned she’d lose all her teeth anyway by the time she turned 60, so why bother brushing? She also claimed they were naturally strong and didn’t require brushing.

The Weight Watchers endorsement

Having figured out tuna, Simpson felt she was qualified to serve as a spokesperson for Weight Watchers – now known as WW – and the company seemed to agree in 2012, paying her a reported $4 million for being their public face. To paraphrase the old infomercial, she wasn’t just a spokesperson – she was also a client, and went on the company’s fabled points system herself, where each food is assigned a point value based on its nutritional values.

Shedding the pounds

Simpson’s collaboration with Weight Watchers was a complete success, and she finally managed to shed those pesky pounds. However, she was forced to put the diet on hold when she became pregnant with her second child Ace. Working alongside the company helped her to feel more comfortable about her body following the birth of her children, although it didn’t push her to lose more than she needed to. Her only focus was returning to a healthy weight.

‘The best version of myself’

Simpson outlined her philosophy in her first television ad for Weight Watchers, in which she said she felt a lot of pressure to lose weight. “But I’m not a supermodel,” she protested, “I’m just Jessica trying to eat real food in the real world.” Her only goal? To stay healthy for her daughter. She signed off by addressing the reason she chose the company to begin with – to become the best version of herself, and it certainly seemed as if she had finally found it.

Business pursuits

The Weight Watchers deal was far from Simpson’s only business endeavor, however. In fact, the singer also founded the Jessica Simpson Collection, which designs and markets a line of handbags, shoes, and boots. Her line is probably the most successful celebrity apparel brand in history, as it was the first to achieve more than $1 billion in annual sales. It’s not surprise, really, as it’s carried by 650 department stores nationwide, including the high-class Lord & Taylor and Macy’s. Her own personal net worth, however, is somewhat more modest.

Crunching the numbers

Simpson’s career in the entertainment industry and her outside business ventures have led her to amass quite a sizeable net worth. She is not worth a billion dollars, as some newspaper and magazine headlines reported, though – that’s just her company’s sales. No, Simpson herself is worth $150 million. It’s not quite a billion, but it’s far cry from being broke. Sadly, her two biggest rivals from back in the day – Britney Spears and Christina Aguilera – once again have her beat, with net worths of $215 million and $160 million respectively.

Tackles over Tony

Simpson faced down controversy before – one that has to do with her love life. Simpsons dated former Dallas Cowboys quarterback Tony Romo for two odd years, breaking up the night before her 29th birthday, incidentally. Before linking up with Simpson, however, Romo was involved with fellow singer Carrie Underwood, who later said she still spoke to him even as he was dating Simpson. Simpson quashed rumors of any feud, however, saying she’d definitely come up to underwood to “say hi.”

Tough decision to make

Simpson announced in September 2018 that she was pregnant once again. Although this was cause for celebration, she’d had to think a lot about whether or not she wanted to go through another pregnancy. It wasn’t the prospect of having a third child to look after that gave her food for thought, but rather the fear of putting on weight again. In the past, she’d allegedly struggled to control her eating habits while pregnant, and she was afraid of facing more criticism in the media because of her size.

An ongoing battle

Luckily, the singer decided that a child mattered more than anything the media had to say about her weight. While she waits for the baby to arrive, she’s continuing to work on her eighth album, the follow-up to the unsuccessful “Happy Christmas” that she released in 2010. Adding to that, Simpson certainly has a lot in the works right now, including the clothing lines that she continues to work on. Despite all the downs she’s had over the years, she’s on the up right now, and that’s hopefully where she’ll stay.

Announcing the arrival

Seemingly not letting anything else affect her, Simpson took to Instagram to announce the pregnancy. Posting a snap of her two kids, Max and Ace, with two large black balloons with white dots, she left fans wondering what was up as she merely captioned the post “SURPRISE…” The first post, which got nearly 134,000 likes, had fans gushing at the possible news, as Jessica had kept coy up to that point and never officially announced the pregnancy.

Speaking her truth

The second post showed another photo of the two kids, possibly taken seconds after the first. This one showed them looking at countless pink balloons, and the accompanying text left nothing to the imagination. “This little baby girl will make us a family of five,” Simpson wrote. “We couldn’t be happier to announce this precious blessing of life.” Her fans were no less ecstatic, liking the post more than 436,000 times and posting thousands of comments congratulating her. For her next trick, she stepped in front of the camera herself.

Showing the baby bump

In the post, titled “My Baby Love,” Simpson looked stunning in a dress that showed her belly. From behind chic sunglasses, the singer placed her hands on her tummy and announced to the entire world that she was expecting a brand new child. It seemed like her days of hiding, or feeling self-conscious, about the way she looked were finally over. At 39 years old, and pregnant for the first time, she was done feeling bad.