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Jessica Simpson is opening up about her experience as a pop star in the early 2000s.
The singer and mogul recalled experiencing feelings of inadequacy at the beginning of her career in the music industry as she spoke to the audience from the stage at her Sunday, Dec. 7 concert at the Foxwoods Resort Casino in Mashantucket, Conn.
“My whole music career, I had a job, and that was to be a pop star, and I tried,” the singer said. “You see. when you’re younger, you never feel good enough, and it’s okay to not feel good enough.”
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In 2025, Simpson released a pair of EPs, Nashville Canyon Part I and II, marking her comeback to music after a 15-year hiatus. The “With You” singer, who recorded the album in Nashville, spoke about how the city transformed her.
“I do love Nashville,” Simpson noted. “It brought me home, to myself. It brought me inside of my heart in a really hard time of my life.”
She added, “I just kind of had to surrender myself to my intuition, to the light that was in front of me. I just focused on that.”
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Earlier this year, Simpson performed on stage for the first time in 15 years at the Recording Academy’s Austin Chapter Block Party at SXSW in Austin, Texas.
“This time, I needed to remember who I was and why I wanted to sing in the first place and all the music that inspires me,” she told the crowd, according to Rolling Stone. “And I needed to forget who they told me to be.”
Simpson was dropped from her label after the release of her 2008 country album, Do You Know. In conversation with Trailblazers Radio, Simpson revealed she was “mad at music” and needed to take a break.
After a 15-year break and eight years of sobriety, Simpson is ready to take on music again.
Speaking with The Cut in February, Simpson opened up about how her songwriting has changed since giving up alcohol.
“I have songs from those times (before her sobriety) that I never released because they just didn’t feel like me,” she explained. “Every time I would write, I was a little afraid of myself. It was almost too much, especially because I was drinking at the time.”
She added, “But once I gave up the alcohol, the fears just diminished. They went away.”
