Jessica Simpson's Winning History of Making the Most Out of Every Opportunity

Let us count the times that Jessica Simpson, who's celebrating her 40th birthday, has turned lemons into sweet, sweet lemonade

By Natalie Finn 10 Jul, 2020 2:00 PMTags
Watch: Jessica Simpson Talks New Book's Success & Not Being Perfect

Jessica Simpson has spent half of her life being inordinately famous, for one thing or another.

Many a time, as it tends to work it, the headlines were for something that had nothing to do with what she was achieving on the creative side of life, and those achievements have been considerable.

Even when her name became synonymous with the best possible outcome when it comes to a celebrity brand, the fact that women of all ages have at least one pair of Jessica Simpson shoes in their closet tended to take a back seat to an ex spilling salacious details, or how much she weighed or why she seemed out of sorts in an interview.

But Simpson herself was never deterred by the noise, or at least not to a point where she strayed irreversibly off course.

Rather, the "I Wanna Love You Forever" singer and Daisy Dukes-rockin' Dukes of Hazzard star always ended up righting the ship—and, after years of letting people waste as much time as they wanted guessing what was going on behind the scenes, she took us on an unvarnished tour of her life in her New York Times No. 1 best seller Open Book (which came out in February, just weeks before the whole world was knocked off course).

While it was full of never-before-heard stories, including the truth about an alcohol and pill addiction that almost took her down, and the revelation that she was sexually abused as a child, the memoir (written in collaboration with Kevin Carr O'Leary) was also a reminder of all the times that Simpson has proved to be infinitely more than the skeptics who thought she was more comic relief than conscientious businesswoman could've imagined.

So in honor of the pop singer and reality-TV star turned billion-dollar business mogul and blissfully busy mother of three's 40th birthday, we're celebrating her triumphs:

Everything Happens for a Reason

"I'm happy I did the show. I'm happy I was married. I'm happy that he was in my life," Simpson confidently told Elle in 2007, a year after her divorce from her Newlyweds: Nick and Jessica co-star Nick Lachey was finalized. "I have no regrets. And I will look you in the eye and tell you that I have no regrets about that. Not one."

Even the massive divorce settlement she paid out: Worth it to close that chapter of her life for good, she divulged in Open Book.

High Road

Simpson was blindsided when, several years after she rebounded with John Mayer following her split from Lachey, the singer sang her praises in intimate fashion in an interview with Playboy that soon became infamous for his explosive turns of phrase.

But Simpson was super cool about it, admitting that she was surprised but, hey, his loss.

"He did apologize, but I mean, at this point it doesn't really matter," she revealed on The View. "I mean, I only thought he was stupid for breaking up with me."

Let's Make a Deal

Word got out Simpson wanted to lose weight, and Weight Watchers had her back, signing her to an endorsement deal in 2012 after she gave birth to her first child, daughter Maxwell

Fashion Star

Simpson's weight has been the subject of countless headlines, some mean-spirited, many admiring, and plenty of them self-generated—but she knows that her own experiences going up and down in size (her journals from 1999 are littered with self-ridicule about "how fat I was," she wrote in Open Book) with her winning approach to selling women's clothing and accessories, which she does to the tune of $1 billion a year.

"I want to make every woman feel confident in what they're wearing," she said at the Forbes Power Women summit in 2014. "I do feel like we're very fashion-forward, but we also listen to the consumer."

Simpson continued, "I have been every size on the planet and I understand women. And I just know how to dress them. I know there's all different kinds. There's life in the whole world beyond L.A. and New York. I understand Middle America and their mindset." 

The Real Deal

Her candor has been known to make people laugh, raise their eyebrows, gasp, etc. But her guilelessness is at the core of who Simpson is—and she knows that's helped her in business along the way, too.

"I'm always a Southern girl at heart," Simpson told WWD.com in 2015. "My friends and family are my everything. They influence all that I do. I feel like I'm a relatable person. I'm completely open and honest with everyone. Whether that's too much openness or honesty, it makes me nonjudgmental. I'm one of those girls you would hopefully want to hang out with. When you have a lot of judgment in the world of design, it keeps you from being as creative as you can be….I'm a risk-taker."

Another Football Player?!

That may have been what some folks were thinking when Simpson, who logged time as Dallas Cowboy fans' favorite scapegoat when she dated Tony Romo, stepped out with retired NFL player Eric Johnson, but it was soon obvious that their relationship wasn't cursed in any way.

Woman of Letters

Simpson had been journaling since she was a teenager for a variety of reasons—"a black one for the end of my first marriage, red for the hope of a love affair, blue for when I wanted to focus on my career and song lyrics"—and Johnson, a big reader, encouraged her to get back into it early in their relationship, a way to purge in the morning whatever thoughts might be preventing her from tackling each day with gusto.

All of those thoughts, feelings and anecdotes became fodder for her best-selling memoir.

Life's Natural Curves

Simpson's journey to attain the fallacy that is the so-called perfect shape couldn't be more relatable. In 2019, she revealed that after Birdie was born she'd dropped 100 pounds the old-fashioned way: by working out, eating clean (though not so restrictively she drove herself mad) and not taking no (from herself) for an answer.

"It's been a lot of hard work," she shared on a Sept. 26, 2019, appearance on HSN. "I have to say that I have worked very hard. Everything that I've been eating is mostly made with cauliflower."

Clearing Away the Cobwebs

In her book, she pinpointed the day where she realized she needed to get clean to Halloween, 2017, when there was just too much activity taking place at her often-busy house on what felt like an overwhelmingly busy day, and—addled by her growing reliance on alcohol and Ambien to make it through most days—she collapsed into tears. 

The next day, her friends had an intervention for her and, thanks to therapy and the support of her devoted inner circle, Simpson has been sober ever since.

In February 2019, finding a moment to herself after yet another hectic day, Simpson—then pregnant with daughter Birdie—wrote in what became the prologue to her book that she was physically pretty uncomfortable, but, "Still, I was present. I kept a promise I made to myself a little over a year before to show up in my own life. To feel things, whether they were the result of bad memories, or good ones in the making...I had to strip away all the self-medicating to feel the pain and figure out what was wrong...Knowing what I had to face was a good sign for me."

Knowing now, thanks to her book, that Simpson was in danger of ending up a mere spectator to her own life, it's especially heartening to learn that she sought help—and that it did, indeed, help.

Because, what a life. It would have been a shame if she wasn't able to truly experience it.