Jessica Simpson opens up about under confidence as a 2000s pop star

Jessica Simpson says she never felt "good enough" as a 2000s pop star.

The singer made the admission during her December 7 concert at Foxwoods Resort Casino. Speaking from the stage, she said she spent the early 2000s trying to fit the mold of a pop star but rarely felt she measured up. 

“When you’re younger, you never feel good enough, and it’s okay to not feel good enough,” she told the crowd.

Simpson has returned to music after a 15-year break, releasing two EPs in 2025, including Nashville Canyon Part I and II. 

She said recording in Nashville helped realign her sense of self during a difficult period. “It brought me home, to myself,” she said, adding that she had to trust her intuition and focus on “the light” ahead of her.

Earlier this year, she performed publicly for the first time in 15 years at the Recording Academy’s Austin Chapter Block Party at SXSW, saying she needed to reconnect with why she wanted to sing and forget “who they told me to be.”

Simpson was dropped by her label after her 2008 album Do You Know. She later said she was “mad at music” and needed distance. Now, after eight years of sobriety, she feels ready to return. 

She explained that giving up alcohol lifted the fear she once felt when writing, allowing her work to feel authentic again.