Jessica Simpson opens up about underconfidence as a 2000s pop star

Jessica Simpson says she never felt “perfect” as a 2000s pop star.

The singer made the entrance during her season on December 7 at Foxwoods Resort Casino. Speaking on stage, she said she had already spent the early 2000s trying to fit the mold of a soft-spoken star but rarely felt she had measured up.

“When you’re young, you never feel good enough, and it’s okay to feel good,” she told the crowd.

Simpson returned to music after a 15-year hiatus, releasing two EPs in 2025, including Nashville canyon part I and II.

She said that recording in Nashville helped her to keep her sense of integration during the difficult period. She brought me home, to myself, she said, adding that she had to trust her feelings and focus on the “light” before.

Earlier this year, she performed publicly for the first time in 15 years at the Austin Academy at the Austin Station SXSW Party, saying that she gets up because she sings and forgets “who told me.”

Simpson was dropped by her label after her 2008 album You know. She later said she was “mad about music” and needed some distance. Now, eight years sober, she feels ready for a comeback.

She explained that giving up alcohol lifted her fear of dealing with things while writing, allowing her work to feel real again.