Ashlee Simpson is looking back at the challenges her older sister, Jessica Simpson, faced in the ’90s—and how those tough moments helped shape her own journey.
In a candid cover story interview with The Cut on Thursday, February 20, the Simpson sisters opened up about the early days of their careers and the pressures Jessica experienced as she broke into the music scene.
“Let’s go back to you when you were signed. We’re in the ’90s. I was at the School of American Ballet,” Ashlee, 40, reminisced, recalling a time when she was just a young ballerina. “I had braces, and I was just a little ballerina. You and Dad came to New York; you got signed. People were d—s back then. It was like, ‘You should be skinny; you should look like this; you should sound like this person.’ I saw so much of that, and I was like, ‘Oh no, f— that. I’m never going to be that.'”
Jessica, 44, nodded, acknowledging the difficult world her younger sister witnessed. “Only because I watched you going through it,” Ashlee said, before Jessica added, “Yeah, you watched me going through it—you watched me getting booed onstage.”
The conversation shifted to the many men in “suits” who tried to dictate who they should be. Both sisters agreed that the industry was built around expectations that didn’t always align with their true selves.
“I had to be a pop star because I signed on to be a pop star,” Jessica explained. “No matter what, there was never going to be enough sales, there was never going to be recouping, because they would put so much into me trying to win. You’re a by-product of this company that’s making them money.”
Jessica went on to explain how the realization of her situation hit home after she was dropped by her country-music label in 2008 or ’09, despite the success of her No. 1 country album Do You Know. “My country record was written in Nashville, and that’s where I felt very much myself,” she shared.
Jessica then reflected on the moment she stood up for herself by refusing to sign “360 deals”—a decision that marked her first act of independence in the industry. “That was the first time I stood up for myself. But I was always defined by having a record deal. I had a record deal since I was 14 years old, so to be at the age of 28, 29 not having a record deal, I didn’t know where I was or what I was or who I was, and I didn’t know who I was working for,” she said.
It was a journey of self-discovery, and Jessica concluded, “It took me a while to realize that I deserved to work for myself.”
Now, Jessica is preparing to release her upcoming EP Nashville Canyon Part 1 on March 21, with the single “Use My Heart Against Me” dropping on February 21.
In an exclusive chat with PEOPLE in February, Jessica described the process behind the new music: “I’d wake up in the morning and write down poetry, lucid dreaming style. And then bring that to the songwriting sessions.” For the track “Use My Heart Against Me,” she revealed, “I woke up with that lyric in my head.”
The song explores the vulnerability of craving someone you can’t have, and Jessica shared, “It’s kind of craving someone that you want again and you don’t care if your heart is used against you—if it’s just for one night. Like, give it over, just for the experience again.”
As Jessica prepares for a new chapter in her music career, it’s clear that both sisters have learned from the past—and are ready to embrace who they are on their own terms.
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