Jessica Simpson Says She Felt Like She Was ‘Constantly Letting People Down’ in the Early Days of Her Music Career

While she’s back with new music, the 44-year-old singer said she often felt it was hard to compete in the early 2000s when she was up against the likes of pop phenoms like Britney Spears and Christina Aguilera.

“I was never gonna win, because I had someone like Britney and Christina ahead of me, who were selling so many more records,” Simpson told Rolling Stone in a new interview published Friday.

“I didn’t want to dance, I didn’t want to wear a head mic. But I agreed to do it, because I worked for Sony, and I didn’t want to let them down, and I felt like I was constantly letting people down,” she continued. “Even myself, probably, because I wasn’t singing words I wrote.”

Things all changed for Simpson when she started actually putting pen to paper, earning her her first number one single, “With You,” in 2004.

Her new music has taken her to Nashville, with the newly single mother of three drawing on inspirations like Brandi Carlile and Patty Griffin, as well as Alabama Shakes and Rosetta Stone to create a whole new sound that really set her apart from who she was in the early aughts.

And while Simpson has a close relationship with singer-songwriter JD McPherson, who she teamed up with when she moved to Nashville, he told Rolling Stone he was skeptical of working with the one-time pop star at first.

“It wasn’t judgment,” he said. “Because if you put me in a studio with everything available and said, ‘Make music that sounds like what she’d done up to that point,’ I would have no idea how to do it. I wouldn’t know what plug-in to use, what microphone to use, who to hire. And then she sent me her inspiration playlist. I was like, ‘Now we’re talking.'”

The track that they created out of that is Simpson’s latest release, “Nashville Canyon,” which was recorded at home in the city with live musicians — a first for Simpson.

“I’d only worn headphones and had a track in my ear,” she explained. “I’d never got to feel the unearthing of a song and breaking it down.”

The track very much draws on Simpson’s evolving personal life — her move to Nashville and the public breakdown of her marriage with Eric Johnson.

Though the pair had quietly separated last year, Simpson announced the end of the former couple’s marriage in January 2025.

“Eric and I have been living separately navigating a painful situation in our marriage,” she said in a January 13 statement. Simpson did not elaborate on the “painful situation” that led to the split.

“Our children come first, and we are focusing on what is best for them,” she added. “We are grateful for all of the love and support that has been coming our way, and appreciate privacy right now as we work through this as a family.”

Simpson first sparked split rumors in November 2024 while teasing her new music, telling her followers, “Interviews in my Nashville music room where I unearthed my singular magic. This comeback is personal, it’s an apology to myself for putting up with everything I did not deserve 🎶 🎼 🤍🖤.”

As she channels her emotion from the split into her new music, Simpson said frustration is a major throughline in the soulful new songs.

“I’m not comfortable with anger, so you won’t hear much anger in any of my music,” Simpson told the outlet. “You’ll hear frustration, but it’s strong. I deserve to love the way I love, and I love so deeply and so fully and in a committed way. Maybe there are others out there like that. Who knows?”

It’s also earned her a level of recognition she maybe didn’t have in the pop world.

“A lot of people are like, ‘I didn’t really listen to your music in the past, but I respected you as a singer, and I feel like this is the most you you’ve ever been,'” she said. “To me, that is success.”