Jessica Simpson at the "All's Fair" Los Angeles series premiere held at DGA (Photo by JC Olivera/Variety via Getty Images)
Jessica Simpson opened up to fans during her December 7 concert at Foxwoods Resort Casino, sharing that she often felt “never good enough” during her years as a pop star in the early 2000s. Speaking candidly between songs, she described what it was like to navigate an industry that expected her to fit a narrow mold, and how those pressures shaped her sense of self.
“When you’re younger, you never feel good enough, and it’s okay to not feel good enough,” she said, reflecting on the emotional weight she carried at the height of her fame. Simpson explained that much of her early career was spent trying to live up to an idea of what a pop star was supposed to be, only to feel as if she constantly fell short.
Now, after a 15-year break from releasing music, Simpson has returned with two new EPs in 2025, Nashville Canyon Part I and Part II. She told the crowd that recording in Nashville played a pivotal role in helping her rediscover her voice and identity. “It brought me home, to myself,” she said. She added that the process forced her to trust her instincts again and focus on “the light” ahead of her instead of the expectations that once controlled her career.
Her return to performing began earlier this year when she took the stage at the Recording Academy’s Austin Chapter Block Party during SXSW. That marked her first public performance in 15 years. At the time, she said she needed to remember why she loved singing in the first place and let go of “who they told me to be.” For Simpson, reclaiming her artistry meant stepping away from the versions of herself the industry had crafted and reconnecting with the creative impulses that first drew her to music.
Simpson’s long hiatus began after she was dropped by her label following the release of her 2008 album Do You Know. She later admitted she was “mad at music” and needed time and distance to process years of exhaustion and frustration. The break allowed her to build a life outside the spotlight, confront personal struggles, and eventually find her way back.
A significant part of that journey included getting sober. Now eight years into sobriety, Simpson said the clarity that followed helped her overcome the fear she once felt whenever she sat down to write. Without alcohol, she explained, her creativity no longer felt clouded or forced. She could finally be honest in her music again, something she considers essential to her return.
As Simpson continues to perform and release new material, she’s leaning into the lessons she wished she had understood two decades ago. Her message to fans was clear: self-worth isn’t defined by an industry standard, and returning to your true self can often be the most meaningful work of all.
Jessica Simpson’s Career
Jessica Simpson released her debut album as a teenager in 1999. The 44-year-old singer has recorded Take My Breath Away, With You, and I Wanna Love You Forever and appeared in several films.
She developed a fashion company from her successful singing career in Texas. Her career and relationships have made headlines, from her marriage to Nick Lachey to their divorce to finding love with former NFL player Eric Johnson and creating a family before their shocking breakup.
Jessica Simpson’s Marriage and Kids
February 2002 saw Jessica Simpson and Nick Lachey’s engagement. Austin hosted their October 26 wedding. Jessica began her third album in 2002. On July 14, 2003, she released “Sweetest Sin, the album’s first single, which failed. Nick and Jessica debuted on MTV in 2003. The show premiered on August 19, 2003. The couple married, and Jessica recorded her new album. The program got popular soon. On-air, Jessica’s levity made them renowned. The MTV hit aired for three seasons till 2005.
Jessica Simpson’s Music and Movies
Jessica began her fifth album in 2005. She revealed her Epic Records signing on March 28, 2006. She quit Columbia Records after seven years. Jessica and stylist Ken Pavés established a hair and beauty collection in 2006. Jessica released “A Public Affair” on June 29, 2006. It peaked at #14 on the Hot 100. The sale of over 500,000 copies earned it gold certification. The day before her divorce from Lachey, she released this uplifting tune.
On August 26, 2006, Jessica released her fifth album, A Public Affair. First on the Billboard 200 at number five. It’s first week sold 101,000 copies. Album sales were lower than those of In This Skin (2003). The U.S. sold little over 500,000 copies. Not a success was the album’s second song, “I Belong to Me. Employee of the Month was Jessica’s comedic film alongside Dane Cook and Dax Shepard. This was released in October. It was poorly reviewed and performed poorly at the box office. In December 2006, Jessica celebrated Dolly Parton by covering “9 to 5.
