Why Ashlee Simpson might be ‘the Pat Benatar of the older ladies’

Ashlee Simpson has a cold, and thank goodness for that.

With three children ages 4 to 16, the singer and actor accepts the certainty that she’ll come down with something every now and again.

“As you can hear, I’m getting through it,” she says slightly stuffily on a recent afternoon amid what she calls the “organized chaos” of her art-filled Encino home. “But it was good timing. Before the show? Look, I’ll take it.”

Simpson, 40, is counting down the days until the opening this weekend of a new residency at the Venetian resort in Las Vegas — a return to the stage after a long stretch away from the pop music career she launched in the early 2000s as the rebellious younger sister of the teen-pop glamazon Jessica Simpson.

As exhaustively documented on MTV’s “The Ashlee Simpson Show” — a spinoff of the trailblazing “Newlyweds” about Jessica’s marriage to Nick Lachey of 98 Degrees — Ashlee released her debut album, “Autobiography,” at age 19 in 2004, topping the Billboard 200 on her first try before watching it all seem to crash down around her when she was caught trying to lip-sync on “Saturday Night Live.” (She later said that acid reflux had left her unable to sing.)

Simpson released two more albums — “I Am Me” in 2005 and the synthed-up “Bittersweet World” in 2008 — then largely left music to concentrate on raising a family. In 2008, she and her then-husband, Pete Wentz of Fall Out Boy, welcomed a son; she and Wentz divorced three years later, after which she married actor and musician Evan Ross, with whom she has a daughter and a son.

Yet while “life happened,” as Simpson puts it, the serrated guitars and snotty-sweet vocals of her early music emerged as a key influence on younger artists making new connections between pop, rock and punk. To look now at “Autobiography” and “I Am Me,” both of which Simpson made in close collaboration with songwriter Kara DioGuardi and producer John Shanks, is to see a point in a line that extends through Miley Cyrus, Paramore and Olivia Rodrigo.

Last year, Simpson celebrated the 20th anniversary of “Autobiography” with a brief nightclub performance in West Hollywood. But the Venetian gig, which kicks off Friday and has dates scheduled through Sept. 27, will feature her first full shows in years. When I visit her, she’s just come from rehearsal with her six-piece band, which includes four women.

“God, it’s been so much fun,” she says as her French bulldog, Banksy, yips at her feet.

You’re doing songs from all three albums?
Yep. Going back and looking at those songs — looking at myself 20 years ago — I’m like, whoa, Ash — I wish I could go back in time and give you a hug.

Why was now the time to do this?
When I did the 20th anniversary last year, I was like, this feels good. It was only three songs, but I felt like I was supposed to keep going. Vegas seemed ideal because it’s close to home, so I can still be there for the kids and I can actually see: Is this right for me?

It’s a test case.
It’s a test, but it’s also something I need. I’ve been needing this. I grew up performing as a ballerina and then dancing for my sister, and I’ve missed it. I miss performing and I miss music and I miss writing — I miss the grind of it. I just want to have fun and throw my hair around and rock out. My band sounds so great.

Was it important to you that the band consist mostly of women?
Yeah, I wanted to use girls because these albums have such a voice of standing up for yourself as a young lady. Writing those records was fully like therapy. Every bridge was like my healing moment.

Which song of yours has the best bridge?
“Shadow”? “Love Me for Me”? That one takes you to this whole different place: “I’ve been waiting all my life to finally find you / Just so I can push you away.” This is about a first relationship, and it still resonates to me as a 40-year-old woman.

The singing on “Autobiography” has real grit. You’re pushing your voice to extremes.
Oh, I’m very aware as I’m redoing it. I’m like, God, I was really ripping there. I loved Courtney Love and Shirley Manson and Fiona Apple. And when I was younger, I loved Debbie Harry and Pat Benatar and Chrissie Hynde.

I was struck going back to “La La.” Pretty racy.
We went there.

“I’ll be a French maid when I meet you at the door / I’m like an alley cat — drink the milk up, I want more.”
I remember being at Henson Studios, and me and Kara were like, “John, leave us alone.” We went out back and put boas on and we had our moment. Kara was like a big sister to me — really helping me find myself and listening to me.

Did she make you feel safe?
She made me feel safe, but she also let the beast out. And she trusted the beast. Finding your right producers and your right writers — it was just us three, and it was just so real and so special. John was strict on me in good ways. He’s like, “OK, little teenage Ashlee — time to focus.” And I loved that because it felt like it was a real teacher.

Ashlee Simpson and her husband, Evan Ross, with their children Ziggy, left, Jagger, center, and Bronx, right, in Los Angeles in 2024.

(Michael Tran / AFP via Getty Images)

It’s clear in retrospect that your first two albums helped clear a path for someone like Olivia Rodrigo. Do you hear the influence?
OK, listen: Yes, I do — thousand percent. But do I think these girls are more talented? Absolutely. Also, I was inspired by the ones before me. Maybe I’m the Pat Benatar of the older ladies. My daughter and her friends, they have the Olivias and the Paramores — to them, I’m like an ’80s singer was in my time, you know what I’m saying?

I was a young girl just letting it out. I’d seen a lot, and I had so much to say from watching my sister get signed, what the label wanted her to be, how fans reacted. So I felt very defensive and strong — like, “Don’t talk about my sister that way.” I think a lot of that fed into who I got to be as an artist because I was like, I won’t do that. You won’t talk to me like that.

But let me be clear — I had a super-high and then I had a super-low at “SNL.” For me, it was such a lesson: You hate me so much because I lost my voice? It was such a dehumanizing feeling that I had to remember who I was and why I was doing this. People’s perception of you is not who you are. Learning that at a young age was — whew! It was intense.

Does “I Am Me” turn out differently if “SNL” doesn’t happen?
I don’t think it would have been as raw. But I’m happy it was because it got deeper. It got darker too — thicker skin yet very vulnerable. When you’re faced with something so traumatic, where the world is looking at a young girl this way, you either hide or you fight and keep going. And I just kept going.

Seems safe to say that the second-most-iconic “SNL” fail was Lana Del Rey’s in 2012. When you saw that —
I can promise you I’ve never seen hers.

Wait, what?
I don’t go and watch people’s bad stuff — I’ve been through enough myself. I mean, I love her as an artist. But I don’t ever harp on things like that or watch people’s failures because I’ve had one. I don’t do that.

Ashlee Simpson at home in Encino.

(Annie Noelker / For The Times)

Why is your third album such a different vibe from the first two?
The third album, I feel like it was so ahead of its time. I’m making it in 2007 — we didn’t have those artists out yet doing the ’80s thing. I was loving Missing Persons and Talking Heads. But I don’t think I was sure where I was going, because I did two different versions. The other version I was writing with Jenny Lewis from Rilo Kiley and Beth Hart. I go back and listen to some of the songs I was doing with them, and I’m like, “Really wish those were in there.”

What’s that version sound like?
More singer-songwriter-y. Then I flipped it and went the other way. I was in this lighter, just-want-to-have-fun place of my life. Some of it feels incomplete as I listen to it now.

I’d love to hear the stuff you did with Jenny Lewis.
She’s, like, my favorite. And Beth Hart — I wrote with both of them. And John Legend! We had three songs we wrote together. I was evolving, right? I was trying to say, “OK, I’m gonna leave that part of me behind.” You have to imagine, I was 23 — no, 22. I got pregnant with my son at 23. There’s so many lyrics I’m still proud of on that record.

Give me an example.
Listen to the words of “Bittersweet World”: “Everybody trying to hide all of those habits / It’s kind of bizarre when it’s who you are / It’s tragic that it’s come to this / I bury all of my vices trying to keep my head up over it when everything’s whatever.” That lyric was saying that everyone has this facade, and I’m seeing life in a different way. I’d been on tour since I was 14, and I wanted to be a mom.

“The Ashlee Simpson Show” was one of the finest reality series of its day — agree or disagree?
The idea that it wasn’t a making-of-the-band but was this insight into what I was doing — it was such a special tool that I didn’t even know. The producers, Matt [Anderson] and Nate [Green], saw me go through everything: My album’s out, it’s No. 1, we’re at Tower Records where now I go to the movies with my kids [at the Sherman Oaks Galleria], they’re with me in New York, “SNL” is happening, I’m going back on tour — they were with me in those moments. And what was so beautiful is that they understood me. I loved them.

Twenty years later, we as viewers are much more cynical about reality TV because we know how much of it is —
Not real.

I can’t say whether your show was truly real or not. But it felt real.
It was real real [laughs]. There were times where I was mean and mad at them and like, “Get out of my face,” because something bad had just happened. And they’d be like, “But we love you and we have to do this right now.” We had this mutual friendship and love, no matter what, and I think the outcome for me was worth it at that time.

You and your husband did a reality show for E! in 2018. How would you compare the truthfulness of that show to “The Ashlee Simpson Show”?
Doing that show was a fun moment to document — making music together was so nice. But having the cameras in our house with our growing family — it didn’t feel as raw or real. And I didn’t want to fully give that either. Evan and I, we’re very protective of our lives and our families. So having somebody in the room with my kids playing wasn’t gonna be right for me.

Sounds like a nightmare, to be honest.
A nightmare as a parent. As a young girl, it’s so different: “Oh, come into my apartment — I don’t know how to mop. Welcome!” The truth is: We tried it, and it wasn’t for us. I won’t be on reality TV again.

Do you regret it?
I don’t because it was a lesson learned: This is not what we want to do.

In 2020 your sister published “Open Book,” which is one of the frankest celebrity memoirs I’ve read.
That’s Jess.

Jessica Simpson, left, and Ashlee Simpson in Los Angeles in 2024.

(Jesse Grant / Getty Images for Janie’s Fund)

I wondered whether her approach made you think about how you tell your story.
She lays it out there, and I think that’s healing for her. She knows it’s healing for other people too — telling your truth does help others. I think we do that in different ways.

She writes that her older daughter reminds her of you.
Max, yeah. Having that sister bond, then having your first daughter — there’s something about it that’s like that. For me, it’s so fun because I’m the aunt that’ll teach the kids to do front handsprings on the trampoline out there. I’m like the gymnastics coach. I might break my back one day, but it’s still rocking for now.

What can you say about new Ashlee Simpson music?
I’ve always been writing. Hearing my old songs come to life in 2025, I feel like it opens these doors of different inspiration for me.

Do the grungy guitars of your first two records still feel relevant to you?
Yes, but I feel like I have such a country thing in all of it too. I’m not saying I would go country — I’m not gonna put a country album out. But I love blues and soul and rock and roll.

The Vegas show is scheduled to run through late September. Is the limited nature of this gig part of why it appealed to you?
Yes at the beginning, but maybe no after rehearsals. I don’t know that I see an end date now. I think it opens a door: Do I want to play shows here? Do I want to try out new material, and what does that lead to? I don’t have an exact pinpoint of what that is, but my heart is open.