Jessica Simpson says she never felt “good enough” as a 2000s pop star.
The singer made the confession during her December 7 concert at Foxwoods Resort Casino. From the stage, she said she tried to fit into the image of a pop star in the early 2000s, but rarely felt like she fit the bill.
“When you’re younger, you never feel good enough, and it’s okay to not feel good enough,” she told the audience.
Simpson has returned to music after a fifteen-year hiatus, releasing two EPs in 2025, including Nashville Canyon parts I and II.
She said shooting in Nashville helped her rebalance her sense of self during a difficult time. “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 had 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 “loved music” and needed distance. Now, after eight years of sobriety, she feels ready to return.
She explained that giving up alcohol took away the anxiety she once felt while writing, making her work feel authentic again.
