Jessica Simpson felt pressure to lose weight to ‘follow’ Britney Spears, Christina Aguilera: ‘Never good enough’

Key points

• Jessica Simpson said that she had to “follow in [the] footsteps” of Britney Spears and Christina Aguilera.

• The singer said that she was expected to “lose 15 pounds” when she weighed 115 pounds at age 17.

• Simpson said that she “always felt like a failure because I was never good enough.”

Jessica Simpson is reflecting on the pressures of teen stardom.

The “With You” singer candidly discussed the challenges of her early career while addressing the audience at her concert in Bethlehem, Penn., on Thursday.

“So when I first started singing, I was — to everyone at the record label — supposed to be this pop star,” she said in a video shared by Page Six. “You know, there’s Britney Spears, there’s Christina Aguilera, we love them, we support them. I had to, like, follow in their footsteps.”

Simpson said that her label placed certain pressures on her physical appearance. “I really thought that I was signed just because of my voice, and all of a sudden it was like, ‘Okay, you need to lose 15 pounds’ — and by the way, I was 115 pounds, so to tell a 17-year-old that is a lot.”

The “I Wanna Love You Forever” singer said that the expectations became more intense by the time her second album, Irresistible, arrived in 2001. “By the second record, I needed to have a six pack — which was definitely not going to happen,” she said. “I’m just not built that way, you know? I have a belly a little bit.”

Entertainment Weekly has reached out to representatives for Columbia Records, the label that represented Simpson during her early career, for comment.

Simpson explained that maintaining her glossy image was emotionally challenging. “There were just all these things that I had to be to be Jessica Simpson, or the version of Jessica Simpson that they believed I should be, that would be successful,” she said. “And I always felt like a failure because I was never good enough.”

The musician also has some fond memories of her early career, and remains appreciative of the opportunities that she was afforded. “I had fun,” she clarified. “And I know that I was in the right moment in the right time, but I learned a lot.”

The challenges of Simpson’s early career led her to change her priorities and approach when she returned to make her first new music in several years, which was released as two Nashville Canyon EPs in 2025.

“When I went in to make new music to heal over the last three years, I was like, ‘I’m gonna do this my way,'” she recalled. “‘I wanna write the whole thing. I have so many thoughts. I have so much to say.’ But I also have so much to be present for this time around.”

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Simpson will next perform in Waterloo, N.Y., on Saturday, and has another show lined up in Kettering, Ohio, on June 22. The singer returned to the stage for a handful of concerts in 2025, marking her first time performing publicly since 2010.

“It’s good to be back on stage in my 40s,” Simpson said in Bethlehem. “I missed all of my 30s. This really, to me, feels like home again. I feel like walking onstage is almost more comfortable than my living room at home. And it’s such a beautiful feeling. It really is.”

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