Ashlee Simpson is underrated and she knows it. The younger, scrappier Simpson sister has never had the glossier career of her older sibling Jessica. In fact, for someone who grew up on stage, had a successful acting career, an MTV reality show and is now married to one of Diana Ross’s children, Evan Ross, Ashlee Simpson has always been an underdog.
In 2004, aged 19, she released her brilliant debut album Autobiography. The process of writing and recording the album was documented on The Ashlee Simpson Show, a reality TV show that attempted to replicate the success of her sister’s show with her then-husband Nick Lachey, Newlyweds. Ashlee, however, isn’t Jessica, and while the show depicted a young woman going through heartbreak and hanging out with her friends, it also offered a rare glimpse into the inner workings of the major label mechanics. Early on in the show, Ashlee meets with her label as they clash over the direction her music is taking. Her label want her to be more like Hilary Duff; Ashlee just wants to be herself.
The show also took viewers behind the headlines. Ashlee’s now iconic and infamous Saturday Night Live lipsync fuck up was a plot device on the show. It was also the grenade that blew apart any chance she had of escaping her underdog status. At the time she was eviscerated in the media, critics and audiences blasting her as a talentless hack who couldn’t sing and who was famous for no reason. “The world hated me,” she said during a recent confessional for her latest E! docu-series she stars in with her husband, Ashlee + Evan.
What many people don’t know is that following the SNL snafu, Ashlee released two more records and toured America relentlessly. Her second, darker album, I Am Me, debuted at Number 1 in America and featured the infectious single Boyfriend. Then there was her final album, released 10 years ago this year: Bittersweet World. Working with Timbaland and Chad Hugo on the record, she blended pop rock with the scuzzy futuristic R&B sound that Timbaland had popularised with Nelly Furtado and Justin Timberlake, creating a unique sound that blurred bratty with brooding. “I do feel Bittersweet World was a little before it’s time,” she says to i-D when we meet. She’s not wrong.
In fact, over the last decade, pop music fans and critics alike have begun to look back fondly on Ashlee Simpson’s discography. Earlier this year, the New York Times dedicated two episodes of its music podcast to Ashlee where they attempted to re-write the negativity surrounding her career. Likewise, Nylon and Buzzfeed have both written pieces praising her, acknowledging how underappreciated she is. When she announced that she would be returning with a new show with her husband, she also announced that she’d be releasing new music with him, too.
Still, with the rewriting of Ashlee’s story, no one has revisited the past with the singer herself. So, during a brief visit to London, i-D sat down with Ashlee Simpson to dive into her colourful career. “Okay, let me get in diving mode,” she says with a laugh, reaching for a Red Bull. “It’s funny, I haven’t had a Red Bull since 2004. Let’s really go back there.”
Re-watching The Ashlee Simpson Show it’s amazing how you held on to your creative vision for Autobiography and stood up to the record label executives. What was that experience like?
Even when I danced with my sister on tour, I had my guitar player come be the guitar tech. I was writing songs at 15. I was into rock and I was this girl figuring myself out. I knew what I wanted the album to sound like. I think it’s an interesting thing with labels and whatnot. I had a great insight because I had an older sister [in the industry] and so I was able to see how labels run and dictate how a person should act or look or sound. I was able to see Jessica be strong and I was able to say exactly how I saw myself.
When you look back are you surprised by how assured you were standing up to the record executives?
For sure! When I look back on my career I’m like, ‘God, I had something to say and I was able to be vulnerable, tough and stand up for who I was.’ Even when the world was crazy and sometimes it felt that people were hard on me, I had the most amazing fans. I was able to be so strong.
One of my favourite bits is when you say you don’t want to be Hilary Duff.
And I love Hilary — she’s, like, my dear friend.
But it’s when you say that if that’s what the label want, you don’t want to make a record.
I definitely didn’t want to be told what to do, how to be or what I should sound or look like. And now it’s interesting because you can now not be with a label and put music out. But when I look back I’m like, ‘High-five Ashlee!’
The album really started to take shape when you met producer John Shanks and songwriter Kara DioGuardi. You had such chemistry.
Yeah. I was talking to John the other day because Evan and I are getting ready to go on tour and I’m getting ready to sing Pieces of Me for everyone. But I had been writing with other people. I had worked with The Matrix on a song. And then I met John and Kara; it was obvious that’s where I was meant to be. It was magic.
What do you remember about writing Pieces of Me ?
I was in the studio when that hook came up. You know, when you write a song like that you know it’s going to be a good one. Kara, John and I all looked at each other like, ‘This is the one.’
It’s amazing how Autobiography hasn’t aged. How do you view it now?
It was my first album! When we were making it I was in the studio every day. It was a magical moment. I’m very proud of it.
I don’t want to linger on SNL.
Oh, I literally don’t care.
But the time it felt that there was an obsession with “authenticity” and “real music” and an opinion that female pop stars weren’t artists. How much do you think the backlash stemmed from that misogyny and mentality?
I think, for me, that was something that just happened. I had vocal nodes and I couldn’t talk. I had done the rehearsal the night before and just didn’t want to go on. Looking back now I wish I had insisted on not doing it. But moments like that made me stronger. When the world questions you, you have to realise who you are as an artist. For me, I had to pick myself up, go on tour and be there for my fans. I had to keep going. There was a fight. I think that it was unfair. Nowadays, I think it’d quickly become old news.
Right?
Yeah. It’s like, this poor 19-year-old girl, let’s rip her apart! Now I look back and want to give myself a hug. And especially because I had been in the studio and written that record.
And it’s personal.
Definitely. I kept writing and wrote my second album. It was one of those things where we have those moments in our lives and it’s how you react to it that defines you. For me it was a fight or flight and I chose to fight.
It secured your underdog status. And when your second album went to number 1 it felt like a win.
Totally. And I even went back to SNL and sang again. No one gave a fuck.
What was your mentality when you were recording I Am Me?
I was definitely in a place where I did feel a bit broken. There were moments where I was searching for that on songs like Beautifully Broken.
Boyfriend is amazing. How did that song come about?
John started playing the riff. That was another of those, ‘What is happening?’ moments. John is amazing.
Would you work on another record with him?
I would! After we’ve done the second EP, Evan and I are going to be working on our own songs and I’m going to bring that sound back but in my own new way, which I guess I have to now discover.
Bittersweet World was a total departure, though.
Yeah. But you know, before I did that album, I had written a song with John Legend and I had written a song Beth Hart and Jenny Lewis. I was writing with all these different people and it was really amazing — in fact, maybe with my new album I need to go back and revisit those songs. But then I took a departure. I was like, ‘I want to have fun’, which is when I went to Timbaland and Chad Hugo. The fun thing was that Bittersweet World was ahead of its time.
Outta My Head and What I’ve Become would work now.
It’s so hard because I got pregnant on that album. Then I go back and listen to it and realise how fun they are.
There’s a bit in the docu-series where you say that you don’t think that people realise that you had a second number one album and toured a lot. Is that frustrating for you?
I don’t take myself that seriously. I’m grown up. I think the people that recognised it are my fans, and they still are. It’s cool to have a certain fanbase that were waiting for me to come. It’s not frustrating. People see people in different ways. Also, it wasn’t frustrating because it was a great tour; I had fun!
Artists like Charli XCX and Haim have said they’re fans of your music. What’s it like hearing those artists are inspired by you?
That’s like… I’m old and it’s amazing. Definitely, that’s amazing to hear. It warms my heart. That’s what I had always wanted. I wanted to make music that was relatable.
Is there anything from that time that sticks out to you now that you can look back retrospectively?
It is hard. When you’re in that moment you’re just going and going. But I look back and listen to those albums and I watch myself and how strong I was when I was younger and how I kept being creative. I’m proud of myself.
Ashlee + Evan – EP is out now. Ashlee + Evan airs on E! UK from 13 January 2019.