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Jessica Simpson Says Pop Stardom 'Never Felt Good Enough'

Jessica Simpson acknowledged her struggles with self-worth during her pop career and marked a comeback with two Nashville Canyon EPs after a 15-year break.

  • On Dec. 7, Jessica Simpson told the crowd at Foxwoods Resort Casino in Mashantucket, Conn., she never felt `good enough` during her pop career.
  • Simpson stepped away because she was `mad at music`, took a long break and later reached eight years of sobriety during a roughly 15-year hiatus after being dropped by her former record label following her 2008 country album Do You Know.
  • Recording in Nashville, Simpson described how it `brought me home, to myself` during a hard time as she journals and says sobriety of eight years diminished fears in her songwriting.
  • Simpson also returned to live shows on March 12 at the Recording Academy's Austin Chapter Block Party during SXSW and released Nashville Canyon Part I and II in 2025.
  • Her pivot to country follows her separation and a Nashville trip with Maxwell, daughter, inspiring roots; she released `Use My Heart Against Me` on February 21 and worked with JD McPherson and Sista Strings.
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Jessica Simpson reveals why she 'never felt good enough' as a pop star

Jessica Simpson opens up about overcoming one of the hardest moments of her life.

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Page Six broke the news in on Tuesday, December 9, 2025.
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