I’m Never Going to Be That: Ashlee Simpson Reflects on sister Jessica's '90s Era

On February 20, the singer-songwriter Ashlee Simpson interviewed her sister Jessica Simpson in a cover story interview for The Cut. In this interview, the sisters discussed the early days of their careers and the challenges they faced.

During the interview, Ashlee Simpson said, ''I’m never going to be that.'' This was said by her after discussing how her sister, Jessica had to go through personal challenges, experiences with fame, and media scrutiny at the start of her career.

The sisters then also discussed Ashlee's early realization regarding her career, industry pressure, identity crisis, and the process of songwriting.

What made Ashlee Simpson say ''I’m never going to be that.''?

The interview begins with Ashlee asking the Take My Breath Away singer about the time when she got her first music contract during the 1990s. At that time Ashlee was at the School of American Ballet. They also shared a fun memory of how Ashlee would be using Kool-Aid to dye her hair.

Then Ashlee said:

''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.''

She continued:

"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.''

Following this statement by Ashlee Simpson, Jessica appreciated her for knowing what she wanted to do with her career from the very beginning. Then the sisters spoke about how difficult it was for Jessica to deal with public criticism. Adding to that, Jessica also spoke about how "so many men" in "suits" told her who she was supposed to be.

Jessica then went ahead to describe how she felt trapped in the music industry, where labels took control of her career and image. She said:

''I had to be a pop star because I signed on to be a pop star. 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.''

She also mentioned the incident when she was dropped by her record label in 2008 or 09, even though she had a No. 1 country album. She then said that she felt most like herself when she made country music, and hence, after Do You Know, when she was offered 360 deals, she turned them down.

Following this, she said:

''That was the first time I stood up for myself. But I was always defined by having a record deal.''

She continued:

''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 wrapped up this topic by saying:

''It took me a while to realize that I deserved to work for myself."

The sisters also discussed whether they should collaborate again, mentioning their Christmas collaboration The Little Drummer Boy. Jessica mentioned how their voices are similar to the band Heart because their tones blend well as siblings.

They agreed that a joint album would be possible in the future if their timings worked out. Jessica is currently working on releasing her new project Nashville Canyon Part 1 on March 21, 2025.