We’ve Got A File On You features interviews in which artists share the stories behind the extracurricular activities that dot their careers: acting gigs, guest appearances, random internet ephemera, etc.

It would be an understatement to say 2004 was an explosion of pop culture. The Razr phone was all the rage, meticulously curating your MySpace Top 8 was a full-time job, the final season of Friends broke millions of hearts, and #Nipplegate became a national debate. And when it came to music, there was a certain pop-punk newcomer who was ready to make history. That’s right: Ashlee Simpson.

Simpson, with her jet black shag and edgy style, emerged as the antithesis to her blonde-haired pop-princess sister, Jessica. With the release of her 2004 debut, Autobiography, Simpson proved she was “moody and messy,” harnessing a grittier sound that evoked Avril Lavigne, Gwen Stefani, Hole and Joan Jett. And the making of the project was captured by the MTV reality series The Ashlee Simpson Show, which helped turn Simpson into even more of a star.

Autobiography, which Simpson largely wrote with Kara DioGuardi and producer John Shanks, was an angsty, 12-track diary entry that was emblematic of the teen girl experience: melodrama, heartbreak, love, and jealousy. Ahead of The Ashlee Simpson Show, the singer shared her lovestruck debut single “Pieces Of Me,” which was followed by the power ballad “Shadow” and the defiant anthem “La La.” During that time, a lip sync incident on Saturday Night Live, notably overshadowed her star turn, an unfair development given how widespread the practice was and continues to be.

Simpson only released two more albums following Autobiography — 2005’s I Am Me and 2008’s Bittersweet World — and made a comeback in 2018 with Ashlee + Evan, a collaborative EP with her husband Evan Ross.

But Simpson and her music have remained revered by many — and with the pop-punk resurgence in recent years, it’s been impossible to ignore her palpable influence, how newer artists like Olivia Rodrigo, Meet Me @ The Altar, WILLOW, and Chloe Moriondo have embraced the defining sonic palette Simpson helped shape in the early aughts.

Just days before Saturday’s 20th anniversary of Autobiography — and Friday’s release of an expanded edition — Simpson is Zooming from Malibu, where she’s trying to escape the heat. It’s been a long time since she’s rocked her dark hair (she’s been varying shades of copper and strawberry blonde for some years now), but her unbridled enthusiasm for her debut album hasn’t wavered.

In an interview with Stereogum, Simpson opens up about the expanded edition of Autobiography, an album she was working on with Jenny Lewis, and making new music.

Growing Up In Texas, Discovering Lilith Fair, And 7th Heaven

Growing up in Texas and alongside your sister who went the more traditional pop star route, how did you get more into alternative music?

ASHLEE SIMPSON: When I was younger, third grade was all Lauryn Hill, all Erykah Badu. I did like Green Day and Nirvana. And then comes Alanis Morissette, Fiona Apple and Jewel. And I remember going to Lilith Fair, and I saw Joan Osborne and all these women being so amazing and so strong, and I was like, “That’s what I want to do.” That was the moment when I realized that’s really what I wanted to do. I wanted to be up there. It moved me. It changed me. I mean, we need a Lilith Fair reunion.

Who would be on your ideal Lilith Fair lineup today?

SIMPSON: Chappell [Roan]. She’s incredible. I like her songs and her whole vibe. It’s so cool. I’d love to see her live. There’s so many amazing women artists out right now that I would love to see, but I’d love to see the Jewels and everyone as well because Jewel and Sarah McLachlan are what started such a beautiful, amazing sound. And I play that for my daughter [Jagger], too. I got to see Alanis two years ago, and I felt like a child again. It was actually a cute moment because when I was in fifth grade, my mom wouldn’t let me go because she said certain swear words. And then it was my birthday and my mom took me.

You were a ballet dancer and backup dancer for your sister. How did you fall in love with dance?

SIMPSON: I’ve danced since I was a baby, and I was a ballerina. I did School of American Ballet, and I always wanted to do theater. There was a moment I was like, okay, I think I’m done with ballet, although it still lives in my bones at almost 40. I still love a little ballet moment with my daughter or just listening to music to do modern dance to. But then when my sister was going on tour, a lot of it was either I could go stay at ballet school and do that or I could go with my sister on tour and dance. That was funny for me because I’m not really a hip-hop dancer, so I was really learning to get down, get low. It was actually so much fun and getting to have that experience of growing up on tour. I lived a different life, but it was a unique and very cool life. I think I realized always in doing that, “Oh, this isn’t forever for me.” So, the next year when I was 15 on tour with her, I had my guitar player come be the guitar tech so I could write songs as well.

You played Cecilia, who dated Simon (David Gallagher), on 7th Heaven for 40 episodes. In recent years, the show has been reevaluated by many TikTokers. Have you ever rewatched it or yourself playing Cecilia, and how do you look back on the show now?

SIMPSON: I haven’t rewatched it, but I did an interview with Beverley [Mitchell], Mackenzie [Rosman] and David [for a new rewatch podcast], and it was so funny reliving those memories. I didn’t even realize I had done [so many] episodes of that show. That was such a fun set, and they were like, “We remember you’d go to your trailer, and you’d be writing songs.” I loved everyone on that set, and Beverley was my good buddy. They would come in and listen to what I was writing or I’d be like, “Listen to this song.” But it’s definitely funny looking at Cecilia and the memories of 7th Heaven. They were saying to me, “We didn’t even know that you were a janitor.” I was like, “Yeah, I was the janitor’s daughter and I would clean the school floors.”

I feel like TikTok revealed it was way more religious than I remembered it being.

SIMPSON: I know. It’s funny because I think you don’t even realize it. When I was on set, I don’t know that I was taking it to heart with the message — or how I would not be parenting some of the certain topics. But all that being said, it was a cute show.

Right before you signed to Geffen, your song appeared on the Freaky Friday soundtrack. You and Lindsay Lohan and Pink Slip had a very similar sound on the soundtrack. Was there ever any talk of collaboration?

SIMPSON: No, we never collaborated, but I watched that movie with my daughter and I was like, “I forgot that my song was in it.” And I was like, “That’s my song. They’re in the car.” So, that was cute. We had another moment like that, and she was like, “Mom, your song ‘Nothing New’ was on Hannah Montana.” It’s fun to see her discover those moments. I didn’t know my song was on Hannah Montana.

The Ashlee Simpson Show (2004)

You and Jessica were two of the earliest reality TV stars. After starring in a reality TV show in the early aughts and again in 2018, how did those experiences differ?

SIMPSON: I think there was such a big change in reality TV. I actually just saw Matt Anderson, who did my first show with me, and we had dinner the other night and we were laughing about good old memories. But I think that there was just something back in the day that was just so organic and winging it. Now, it feels like it’s changed a lot, but back then it was just like, “Okay, I’m going to the studio today. I’ll be there at this time.” And then they’re like, “Okay, we’ll be at your house.” There was this moment of just going with me and going with the flow. Also, the difference of when I did it in 2018, I have a family, so it’s so much to protect. It was a different vibe, but we had fun doing both.

Would you say that your dad was the OG Kris Jenner — a “dadager”?

SIMPSON: He definitely was the “dadager,” and looking back, I see how he fought for us in a different way, which you navigate through changes in life. But you see that he was definitely on your side and fighting for you in a way of a strong love.

What do you feel like is the legacy of The Ashlee Simpson Show in the context of series about artists being made like Making The Band or Popstars?

SIMPSON: I never really watched those shows, but for me, it was just a time of taking everyone on my journey. And I mean, we’ve had some very funny moments. They were with me through everything: my 21st birthday, the studio, there was moments where I locked myself out of my car, and I drove to Orange County. It was such a journey, and I think that the point of that show was to take everyone along with me on that — and finding myself as an artist, finding myself on tour and whatnot. We were laughing about the day that I dyed my hair dark. [Matt] was like, “Oh my gosh, what are we going to do? How are we going to do her interviews?” I was like, “We’re just going to do them with dark hair. That’s how it’s going to go.”

On the topic of dyeing your hair, was that really a decision made by you, or was it made by the label?

SIMPSON: No, they [the label] were all shocked. I dyed my hair the day I wrapped on 7th Heaven, and I had been making my album while I was on that show. You had to have, for continuity, the same hair. So the day I finished, I went to Ralph’s, got a hair box, and dyed my hair. Then, the next day I had the video shoot for “Pieces Of Me,” so I had to call everyone that night and be like, “Warning, I have dark hair, I have brown hair at this moment.” And then it got darker and darker into a black.

Your sense of style on the show and during the Autobiography era became so definitive of the time and the pop punk aesthetic. Is there any look you particularly regret from either the reality show or your music videos and appearances?

SIMPSON: There’s definitely looks where you’re like, “Wow, what was that?” But looking back, I’m kind of happy I did it, because, man, I don’t know that I’d ever wear wrestling boots and a skirt with a tank top and a T-shirt under it ever again. But this is what the moment was, and I feel like that’s what’s so fun about it. And those tutus, my fans would come out wearing those long skirts with their Converse. I feel like I don’t regret it because that’s kind of the fun about it.

There is a scene in episode 3 where an A&R guy says that Jordan Schur, the then-president of Geffen, says one of your songs sounds like “garbage.” You looked like you wanted to cry, but he was really referring to the band Garbage. At the time, did you know who Garbage was?

SIMPSON: Oh my God, yes. I’ve always been such a Shirley Manson fan, and I knew even when I signed to Geffen that they were over there. I wonder if they did that in editing because I definitely have always been a huge Garbage fan. [Shirley] was definitely somebody I looked up to.

During episode 8, you meet Jay-Z and rap-sang “99 Problems” to him on TRL. How do you look back on that interaction?

SIMPSON: I do remember it. I need to go back and catch that moment. But I was always a Jay-Z fan. And I think there’s a fun moment of innocence, as well. You’re meeting people that you’re like, “Wow, here I am at MTV and there’s Jay-Z.” And what do I do? I just sing a song. Now it’s kind of funny because people are like, “Oh, it’s Ashlee. Oh, ‘Pieces Of Me.'”

There was a lot of sexism that surfaced on The Ashlee Simpson Show from older men including John Shanks and Carson Daly. Have you gone back and watched some of the comments that were made?

SIMPSON: I haven’t gone back and watched that, but I am interested to. I think you go through those moments, and now it’s so beautiful because everyone has such a voice for themselves. But I haven’t really watched those moments, but [those guys] were great and I think that they probably wouldn’t be saying anything like that now.

“On The Way Down” (2004)

Your and Ryan Cabrera’s careers really kicked off at the same time — you starred in the “On The Way Down” music video around the same time “Pieces Of Me” was released — what was that experience like for you?

SIMPSON: We were such good friends. We were always friends first and friends after [dating]. So I think that it was kind of actually just nice to have somebody go through that moment of success at the same time. We could understand each other, and that was nice. But “On The Way Down,” when I shot that with Ryan, he wasn’t my boyfriend. We were just friends.

How high was Ryan’s hair at the time?

SIMPSON: So funny. Very, very high and straight up. Like Sonic.

Autobiography (2004)

Your career began taking off around the same time as Paramore really came out. Do you think the success of Autobiography had an influence on Paramore getting signed to Atlantic?

SIMPSON: Oh, I have no idea. I mean, [Hayley Williams] is amazing and continues to be so amazing. I think that maybe it was just a fun time in life and music and girls really getting to express themselves. [We were able] to have a voice, be rock and be punk and be like, “I don’t care.” And that’s really how I felt at that time.

Was “La La” always meant to be a single?

SIMPSON: I never wrote songs saying, “Oh, this is the single,” but I think as we were writing that one, it felt like, “Oh, this is something that is special and fun, and I wonder what this is.” For me, “La La” is an anthemy fun song. We need a 2.0 “La La.”

The lyrics in “La La” are still so wild (i.e. “I’m like an alley cat/ Drink the milk up, I want more”). Tell me about how you came up with them.

SIMPSON: Well, Kara and I got boas. We were going as far as we could with that, and her and I were having the best girly party time. We were at the Henson studio. We would go outside and come up with crazy words, and then we’d come back in. There were actually lyrics that I had to take off of there, too. So there was a switch up in some of them. But I think we were trying to go as far as we could with it all.

You’ll be releasing an expanded edition of Autobiography on Friday. Are these never-before-released tracks?

SIMPSON: Well, the extended version is just songs that I didn’t release in the States.
It’s songs that I would perform [like] “Harder Everyday.” I wished that was on Autobiography. I loved that song. I wrote that with John Feldman years ago, actually, and the Madden brothers, so it’s going to be that and a few of the other songs that I wrote a while ago. But I am in the studio making new music…so that will be coming.

Are you working on an album or just singles?

SIMPSON: Right now I’m working song by song, and then we’ll see. I’m sure it’ll end up turning into an album. But [I’m] just enjoying the process, getting back to the studio and enjoying writing again.

Does the new music still have a pop-punk vibe to it? Obviously Ashlee + Evan went in a bit of a different direction.

SIMPSON: I’ve grown up now, so it’s a little bit more grown, and at the moment, it’s been more with live music, so I feel like the direction can always turn, but I’m really happy with where we’re at right now. [It’s] more of the fun, rocky vibe.

Will you be doing any live shows or touring for the Autobiography anniversary?

SIMPSON: Yeah, we are hoping to. Right now I’m doing a fun club performance on July 20 [in Los Angeles]. I want to celebrate and have a good time with the fans. That is not a show. It’s more just for fun, and maybe I’ll sing “Pieces Of Me” and “La La,” but I wanted to celebrate and sing with everyone. I’m looking to do some actual shows coming in November, December, coming in the new year.

Who do you dream of collaborating with these days?

SIMPSON: For me, there’s so many people that I would love to work with. I like the good old classics, Alanis, Fiona Apple, Jewel. But then right now, I really love Chappell. She’s amazing. I really love her whole album.

Who are your favorite alternative artists right now?

Oh man, I don’t know, My son Bronx listens to such a wide variety of music, but he’s really brought back lately MGMT, and I’m like, “This needs to be right now. It’s so good.” But who am I obsessed with right now? I don’t know all the new artists. I still go back to my classics. I like Father John Misty. I like that “Real Love [Baby]” song a lot.

The SNL Lip-Sync Incident

Back in the day, you received a ton of criticism for lip-syncing on SNL, and you’ve spoken out about how you had vocal issues that day. In retrospect, how do you feel about the backlash you received?

SIMPSON: There was a lot of backlash, and I think that what I mostly experienced was discovering my strength in myself and also in my fans because they were so loyal to me — the fact that I got to get up, fight, and they all watched me do that and come to my shows. So, I think I learned a lot about strength and speaking up for yourself. But there was definitely backlash, but I think that comes with the territory, and it was definitely a heightened time of craziness for that. I personally think it was a bit ridiculous, but also, shit happens. You’ve got to learn from it.

I Am Me (2005), Miley Cyrus’ Cover Of “Kicking And Screaming,” And Writing with Pete Wentz

“Boyfriend” was the lead single of I Am Me, and back in 2018, you essentially confirmed on Watch What Happens Live that the “I didn’t steal your boyfriend” lyric was about ex-boyfriend Wilmer Valderrama and Lindsay Lohan. Did they ever reach out to you and respond to the song?

SIMPSON: We’re all friendly. I mean, at that point you’re just kind of writing about things that you’re going through daily. So no, nobody was offended on certain things like that. I feel like that’s just writing, expressing and also taking things to a severe level, too.

“Kicking And Screaming” was featured as an international bonus track on I Am Me, and Miley Cyrus ended up covering it a couple years later on her The Time Of Our Lives EP.

SIMPSON: Which I now know because my daughter was like, “Listen to this, Mom.” I was like, “I wrote that.” [She heard it] from listening to Hannah Montana Spotify.

The song was co-written by you, but you didn’t get a writing credit on the EP. Did you push back on that at all?

SIMPSON: No, I didn’t push back.

Did you and your ex-husband Pete Wentz make music together? Is there a secret pop punk collab out there?

SIMPSON: We definitely wrote together. We definitely wrote lullabies.

Working With Timbaland, Bittersweet World (2008)

On Bittersweet World, you worked with Timbaland. How did that happen, and what kind of artist did you want to be or did the label want you to be at that point?

SIMPSON: It was actually interesting because, at the time, I was writing two separate albums. At first I was working with some of the people I really looked up to, like Beth Hart and Jenny Lewis, and doing more of probably what I would do today. And then I think I just was in this place where I wanted to do something fun, and the song “Outta My Head (Ay Ya Ya)” was [written with] Santigold, who I’m obsessed with. It was more of “let’s let loose and make a fun, quirky album.” I was influenced by that ’80s kind of a vibe.

Do you feel like that record was ahead of it’s time?

SIMPSON: Yeah. I had a lot of fun making that album, and then I got pregnant, and then that decision for me was to really focus on that part of my life. But I had so much fun making that album, and I do feel like that kind of sound came right after it.

Why was Bittersweet World the last album that you released?

SIMPSON: Oh, I don’t know. I just think I’ve been in this place so much of parenting that every time I’ve been like, “Okay, I’m going to do this,” or I have another baby, or this one’s going through this. For me, [parenting] is my first priority, and that’s always been my first priority and will always be. Now, I feel like I’m at a time where my daughter wants me to [do music] so much as well, and I feel like I’m at a place where it feels like it would feel organic and right. There’s nothing that I’m expecting from it. And my daughter wants to get up and sing with me on stage, so I’m definitely going to get out there and do some shows.

Ashlee + Evan, Playing Her Music For Diana Ross (2018)

On your reality TV show Ashlee + Evan, you and Evan played your song “I Do” for your mother-in-law, Diana. What was it like having her listen to your song right in front of you?

SIMPSON: Look, it’s my mother-in-law, so I feel like playing a new song for her or, honestly my mom too, or your friends, you’re like, “Oh my God, is it okay?” It wasn’t as nerve-wracking as maybe it came off as, but it’s always nerve wracking playing a new song.

Has she listened to any of your solo work and is she a fan of any of your songs from over the years?

SIMPSON: Yeah, she’s definitely listened to it. I’ve definitely sang her songs that I didn’t put out. I mean, I think she’s a fan of me. I think she loves me a lot — I’m her daughter-in-law!

Is she rocking out to “La La” like the rest of us?

SIMPSON: She’s been to the shows and seen me do the melody of it and everything.

Performing “La La” With Demi Lovato (2022)

Two years ago, you were a surprise guest at Demi Lovato’s show in Los Angeles where you performed “La La” together. How did that come about?

SIMPSON: Well, I had heard that [they were] doing it on tour, and when she was coming to LA, she just asked if I would jump on with her. So I was honored to do that. I love her, great artist. [Their] voice is incredible, and she puts a great show on, so it was super fun to jump on there.

What was it like for you being on stage for the first time in a couple years?

SIMPSON: It was fun. I feel like the energy was amazing, and it was such a fun moment of being like, “Oh, this feels so good. I miss this.”

The expanded edition of Autobiography is out 7/19. Pre-save it here.