Ashlee Simpson Ross Meets World

Summary

Pod Meets World – "Ashlee Simpson Ross Meets World"

Podcast: Pod Meets World (iHeartPodcasts)
Date: August 21, 2025
Hosts: Danielle Fishel, Will Friedle, (Rider Strong absent due to internet issues)
Guest: Ashlee Simpson Ross

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Episode Overview

In this nostalgic and heartfelt episode, Danielle Fishel and Will Friedle sit down with Ashlee Simpson Ross ahead of her Las Vegas residency at the Venetian, reflecting on her music career, her journey from ballet prodigy to pop stardom, and the highs and lows of growing up in the spotlight. The conversation dives deeply into themes of resilience, reinvention, and self-compassion, with candid insights into Ashlee’s family, creative process, and experiences in both the music and acting industries.

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Key Discussion Points and Insights

1. Ashlee's Vegas Residency & Return to Music

• Preparation and Excitement
  Ashlee talks about the emotional and logistical preparation for her upcoming Vegas shows at the Venetian, describing the excitement of revisiting her early songs with a new, more mature perspective, and assembling an increasingly female-led band.
  • "For me to revisit the things I wrote when I was 18, 19, 20—revisiting that has been so much fun for me. And just, like, bringing it to 25 right now…" (21:59)
• Inspiration from Her Children
  Ashlee shares a sweet anecdote about how her daughter and daughter’s friends “discovered” Ashlee’s music, inspiring her to return to performing:
  • "My daughter, like, all of a sudden, her and her friends were like ‘hello, hello.’ Like, I was like, how is this happening? I’m like Pat Benatar to you!" (22:30)

2. Las Vegas Show Origin Story

• Ashlee and her husband discussed returning to the stage following a 20th-anniversary mini-performance that left her wanting more.
  • "When the three songs were over, I was like, that's it. I wanted to keep going." (23:22)
• She notes the “nostalgic and sexy” energy of Vegas and seeing Diana Ross (her mother-in-law) perform as further inspiration.

3. Reflecting on Past Work & Growth

• Revisiting Old Songs
  Ashlee expresses pride and compassion for her younger self, discussing past insecurities and the process of self-acceptance:
  • "You always found it. Even though you were young and going through so much… Like as a 40-year-old woman, I’m still able to connect that and see so much of that and I’m like, ooh, yeah. Girl, you’re proud of young you." (27:09)
  • Danielle adds: "Isn’t it nice too to be able to look back and give that younger version of you that you were so hard on a nice hug?" (27:15)

4. Early Life and Career: Ballet, Family, and Moving to Los Angeles

• Ballet Prodigy
  Ashlee was the youngest ever admitted to the School of American Ballet at age 11. She describes her mother’s support and her early dedication.
  • "By the time I was in third grade, I was on point, so I was like dancing with 17-year-olds by the time I was… very young." (29:14)
• Transition to LA and Music
  After her sister Jessica Simpson was signed to Columbia, the family relocated; Ashlee chose to follow and eventually began backup dancing for Jessica.
  • She recounts feeling protective of Jessica in the media spotlight and learning from observing her sister’s experiences (32:15).

5. Acting and Music Industry Comparisons

• Ashlee discusses both industries’ similarities and challenges, emphasizing the importance of remaining grounded and defining self-worth outside of success or public opinion.
  • "Whether you’re an actress or a singer… it’s not letting people dictate what you are or any failure or this audition or that… but dictating who you are or your self-worth." (35:11)
• She fondly recalls her time on "Seventh Heaven" and the supportive environment on set.

6. Ashlee's Iconic Hair Transformation

• After "Seventh Heaven," Ashlee famously dyed her hair brown with a box from CVS, reclaiming control over her image and marking the beginning of her signature look.
  • "I just want you to know I have brown hair and it’s from a box at CVS." (37:32)

7. The Autobiography Era and Family Dynamics

• "Autobiography" (2004) was described as a raw diary of her life at the time. Recent acknowledgment by media (Rolling Stone, NY Times) is discussed as validating.
  • "It was literally like the diary of my life." (43:47)
• Ashlee and Jessica Simpson’s tight bond and family support are highlighted, giving context to their mutual success and well-being.
  • "It’s this unspoken understanding of everything, everywhere we’ve been… I think just having Jessica has just been a lifeline, honestly." (44:54)

8. The Reality TV Experience

• Ashlee discusses "The Ashlee Simpson Show" as ahead of its time but admits to occasional regret now that her daughter is old enough to watch old episodes.
  • "The only thing that kills me is, like, my voice… but I think for me, though, it was so important because it was such a window to my life and what I was thinking, what was changing." (46:18)

9. Songwriting Process and Creative Teams

• Ashlee describes her creative approach:
  • "You start with the concept, then you get a guitar, and then… melodies… In those sessions, it was me, John [Shanks] and Kara DioGuardi, and we were like an incredible team." (48:13–49:08)
  • Reflects on the organic, almost magical nature of songwriting:
    • "You don’t write a song, like, it’s given to you by some other universe. Like, it just pops in." (50:12)

10. Parenting and Industry Lessons

• Discusses intentionally not pushing her children toward the industry, and instead prioritizing development and personal choice.
  • "I would never push it… the most important thing in this age is developing your craft and deciding what you want with it." (51:06)

11. Acting & Theatre Aspirations

• Ashlee expresses interest in returning to acting, with theatre as a particular love.
  • Recounts playing Roxie Hart in "Chicago" on the West End, Broadway, and the Hollywood Bowl. (52:45–53:19)

12. SNL, Internet Culture, and Resilience

• The hosts bring up the infamous SNL moment as a harbinger of internet bullying and evolving public discourse.
  • Ashlee is candid about the toll: "I think during that time, I mean, the bullying was insane. Insane… But I do think it’s evolved. But also it hasn’t, you know, in some ways..." (54:31)
  • She emphasizes her journey to recognizing her own worth—measured by the connection to fans and her authenticity.

13. "Bittersweet World" Album – Retroactive Praise

• Ashlee discusses her bold sound shift, working with producers like Timbaland and Chad Hugo, and reflects on being ahead of her time as an artist.
  • "It was before—there’s, like, a lot of big artists out that ended up doing that sound. So it was like kind of the beginning again." (56:11)
  • Recent recognition by Rolling Stone and the New York Times as "redeeming" and "a big pat on the shoulder." (58:28)

14. Musical Influences

• She names The Pretenders, Blondie, Debbie Harry, Joan Jett as key influences.
  • "They were like women of strength…so cool and, like, rocking." (59:26)

15. Looking Forward and Advice to Younger Self

• Ashlee hints at new music but is savoring her current moment.
• Her message to her younger self:
  • "You are doing good… to look at yourself and say, wow, like, you are doing so good. Look at yourself." (61:30)

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Notable Quotes & Memorable Moments

• Ashlee, on nostalgia and validation:
  "All those moments led to this, to me to like, be here now and I'm so excited… Now they're all adults—the kids that were like 9 and 11 that came to my show back in the day, they're like grown, grown ups." (27:46)

• On the pressures of fame:
  "No matter what industry you’re in, life just throws [highs and lows] at you. Giving yourself a big hug for the fact you have always remained authentic." (36:37)

• On songwriting and feeling ahead of the curve:
  "There was some songs… when I hear it, I’m like, God, I wish I could have, like, rapped that. Or, like, you know, go back. But I’m so proud of the album because I was taking such chances." (56:54)

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Timestamps for Important Segments

• [21:59] – Ashlee on preparing for Las Vegas shows and the significance of revisiting old music
• [22:30] – How her daughter inspired her to return to performing
• [23:05–23:57] – Origin story of Vegas residency
• [27:09–27:42] – Discussing pride and compassion for her younger self
• [29:07–29:49] – Ballet background and support from her mother
• [32:15–33:24] – Role as Jessica Simpson’s dancer and lessons learned
• [35:11–36:11] – Contrasts between the music and acting industries
• [37:32] – Iconic hair transformation after "Seventh Heaven"
• [43:36] – Creation of "Autobiography": teen angst and authenticity
• [46:18] – Reflections on reality TV experience as a young artist
• [48:13–49:08] – Songwriting process and creative partnerships
• [51:06] – Ashlee on parenting and the industry
• [52:45–53:19] – Love for theatre and “Chicago” roles
• [54:31] – Addressing SNL, bullying, and internet culture
• [56:11] – Creating "Bittersweet World" and being ahead of her time
• [59:26] – Musical influences growing up
• [61:30] – Advice to her younger self before the Vegas shows

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Episode Tone & Takeaways

The tone is warm, supportive, and deeply nostalgic. Ashlee’s groundedness and willingness to openly discuss struggles, healing, and creative evolution make for genuinely inspiring listening. Danielle and Will complement the conversation with personal anecdotes and industry camaraderie. Fans of pop culture, 2000s nostalgia, or “Boy Meets World” will find new appreciation for Ashlee’s legacy and the enduring power of self-acceptance and reinvention.

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Closing Thoughts

Fans—and the hosts themselves—agree: Ashlee Simpson Ross is back in the spotlight on her own terms, with a legacy finally getting its due. Her message of self-compassion, resilience, and living authentically resonates powerfully, whether you're a 2000s kid or not.

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Summary by Pod Meets World Podcast Summarizer – August 2025

Transcript

[Ashley Simpson Ross]

This is an I Heart podcast.

[Danielle Fishel]

Hey parents, quick question. When's the last time you won snack time? Yesterday I packed a granola bar so old Adler asked if it was a dinosaur fossil. So it's been a while. And that's why Mott's no sugar Added applesauce pouches are perfect to keep on hand. Real apples, no added sugar. And the pouch? It's snack times mvp. Minimal mess. Maximum peace. It's even got vitamin C. Kids love it. Parents don't mess it up. Win win Mottz Real apples make real good applesauce. Learn [e-mail] okay, so Amazon prime is the easiest and fastest way to get anything delivered.

[Will Friedle]

But there's so much more. Whatever you love, that's what prime is. Prime helps you get more out of your passions and even discover new ones.

[Danielle Fishel]

Running a household with a four and six year old, I have become a connoisseur of children's toys. And not only can Amazon prime get me what the boys want as quickly as possible, which honestly and save my day, it also suggests new toys, ones I didn't even know existed, sending me down a rabbit hole of robots, ninja hybrids, and happy puppets.

[Will Friedle]

We've all come to know Amazon prime as a lifesaver. It's where I go to stream movies and listen to music. It just keeps on giving. From streaming to shopping, it's on Prime. Visit Amazon.comprime to get more out of whatever you're into.

[Danielle Fishel]

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[Will Friedle]

And if you don't have yours yet, you'll find it on ebay.

[Danielle Fishel]

Putting you on here fashionistas.

[Will Friedle]

Ebay is where you'll find those one Of a kind. Can't stop researching. Stay up. Dreaming about pieces again and again.

[Danielle Fishel]

I'm talking that mew mew off the Runway red leather bomber, the cousteau Barcelona.

[Will Friedle]

Top with the cowboy on it, or that Patagonia fleece in the 2017 colorway. All these finds are on ebay and.

[Danielle Fishel]

They even offer millions of main character pieces backed by authenticity guarantee.

[Will Friedle]

Ebay is the place for pre loved and vintage fashion. EBay, things people love.

[Danielle Fishel]

You can make a difference in someone's.

[Ashley Simpson Ross]

Life, including your own. With a job in home care.

[Danielle Fishel]

These jobs offer flexible schedules, health care.

[Ashley Simpson Ross]

Retirement options, and free training.

[Danielle Fishel]

They also provide paid time off and opportunities for overtime.

[Ashley Simpson Ross]

Visit oregonhomecarejobs.com to learn more and apply.

[Danielle Fishel]

That's oregonhomecarejobs.com.

[Will Friedle]

We used to get this free Pinkberry from this guy all the time. And Danielle and I were like, oh, my God, he's gonna get fired. And when I tell you he would give us free Pinkberry every single time.

[Danielle Fishel]

And we went pink. Well, you're the part you're skipping that's important is we went to Pinkberry seven days a week.

[Will Friedle]

Oh, my God.

[Danielle Fishel]

Every single day.

[Will Friedle]

Which one?

[Danielle Fishel]

At some point. The one on Sunset when we used to live in. In West Hollywood.

[Will Friedle]

Okay.

[Danielle Fishel]

And every single day we would go in there at some point and get Pinkberry. And if he was there, he would just give it to us for free. Every single time.

[Will Friedle]

Every time.

[Danielle Fishel]

I, as you know, don't love free stuff.

[Will Friedle]

No.

[Danielle Fishel]

Because I feel obligated. And a half the time I would only have 20s and I would want. And so then I would end up paying $20 in the tip jar for.

[Will Friedle]

For your free Pinkberry.

[Danielle Fishel]

Than if you just, you please just charge me for the Pinkberry because I'm losing money on the tip in the tip jar.

[Will Friedle]

But yeah. And then we did it. And we'd say, he's going to get fired. And we'd say, he's probably just a huge Boy Meets World fan. Like, this is insane.

[Danielle Fishel]

So weird because he never said anything. Never said, like, I loved you on Boy Meets World. Nothing. And then after about six months of.

[Will Friedle]

Going there, I mean, hundreds of dollars.

[Danielle Fishel]

We get Pinkberry and another person serves it to us and says, no, I'm not allowed to charge you, Josh. Josh would be mad if I charged you.

[Will Friedle]

We were like, oh, my God, now he's involving other people in his scheme.

[Danielle Fishel]

This is so weird. Then the next time we go, Josh is there, and he goes, oh, I heard you met my, my, my co worker Last time. And I'm glad he didn't charge you. He would have been in trouble. And we were like, huh? Yeah. And he goes, this is embarrassing, but I. I have to ask. And I go, what? He goes, were you on a TV show? And I said, yeah, I was on Boy Meets World. He goes, that's so funny. I. I've never seen it, but my co worker told me that. That you were, so I didn't know. I'm so sorry. I didn't know.

[Will Friedle]

He said, that's cool.

[Danielle Fishel]

He said, that's pretty cool. All right, have a good day.

[Will Friedle]

So why is he giving you free? Do you still not know? Is there no end to this story? There's no end to the story.

[Danielle Fishel]

There's no end.

[Will Friedle]

Oh, you're killing me. So you still don't know?

[Danielle Fishel]

No idea.

[Will Friedle]

Hundreds of dollars.

[Danielle Fishel]

Oh, my. Hundreds of dollars of Pinkberry. And we don't get it. And I also got Captain Crunch on it all the time. Totally chewed up the roof of my mouth.

[Will Friedle]

Captain Crunch is amazing. And the only reason I'm upset with having left social media is one of my first tweets was, how has Captain Crunch never been promoted? Because, come on, his guy's been a captain for years. He's obviously doing something wrong. And Captain Crunch himself, from his verified account email, tweeted back and said, because Admiral Crunch makes no sense.

[Danielle Fishel]

Oh.

[Will Friedle]

So I was like, okay, this is why people do social media, because.

[Danielle Fishel]

Right.

[Will Friedle]

Captain Crunch himself.

[Danielle Fishel]

Absolutely.

[Will Friedle]

The real Captain Crunch.

[Danielle Fishel]

Yeah. Yeah. The real. I'm sorry, it's Cap'.

[Will Friedle]

N. Well, it is, but he's a captain. But still, it's captain. I want to know what's going. You know, he's got to have some. Some serious problems to not be promoted to actor.

[Danielle Fishel]

I know. No, you're right. That's been a long time.

[Will Friedle]

Yeah, he's been. Maybe he's giving away free Pinkberry to customers. That could be it. It could be it. He could be Josh's uncle. I'm dying to know what Josh is thinking as he's just giving away. And. And. Cause it's. It would be one thing if it was like, okay, you know, I always give. But to then bring in his co worker to say, I'll be pissed if you charge these people.

[Danielle Fishel]

Yeah.

[Will Friedle]

Also, the co worker definitely knew who she was, so how did you even not have that conversation with the co worker?

[Danielle Fishel]

That's what. Doesn't make any sense, to be honest.

[Will Friedle]

I've always suspected she's you. So it's not that he had a Crush on you? No, I mean, it is, but Jensen's there, so it's not like a pretty girl.

[Danielle Fishel]

No, no. Yeah. I don't know. It's a very. It's a mystery. It was the mysteries of the universe.

[Will Friedle]

It was genuine when he told us. It looked so real.

[Ashley Simpson Ross]

Oh, my God.

[Danielle Fishel]

Mystery of the universe. I don't know what to say about it.

[Will Friedle]

Amelia Earhart. Sean Benet. Joshberry.

[Danielle Fishel]

Joshua Pinkberry. Yeah, those are the things, man. Yeah. Pretty nuts.

[Will Friedle]

Is Pinkberry still a thing?

[Danielle Fishel]

Yeah, there's one in Northridge.

[Ashley Simpson Ross]

Okay.

[Will Friedle]

Never had it in my life.

[Danielle Fishel]

We took Adler to Pinkberry for his first ever frozen yogurt. And I'll never forget it because Adler had never had it before. And so he takes a bite of it and he's like a little hesitant at first, and then he's like, oh, yeah, this is pretty good.

[Will Friedle]

This will work.

[Danielle Fishel]

And then he takes another bite, and he takes another bite. And then all of a sudden Jensen goes, what's happening? And I just look at Adler and Adler's like this.

[Will Friedle]

His eyes are just bulging out. There's like his mouth is shivering.

[Danielle Fishel]

He's like. And I go, oh, God. Oh, wait. He has a brain freeze.

[Will Friedle]

Brain freeze. First ever brain freeze.

[Danielle Fishel]

First ever brain freeze. And I just fully saw it. He was like, what's happening?

[Will Friedle]

What's happening? What's happening? And then when it stopped, he looked at us like I was gonna die.

[Danielle Fishel]

This feels so much better.

[Will Friedle]

That's it.

[Ashley Simpson Ross]

Yeah.

[Will Friedle]

No, the. The first time I ever learned that the way my brother and sister in law raised my nephews, far different than I was raised is we were in Amsterdam and they were little, little kids. And we found one ice cream shop all the way across the city, still open, and the adults wanted to go out, do something. So I said, you know what? I'll take the boys and we'll go and we'll find ice cream. And we walked through the streets of Amsterdam for like an hour to get to this place. And we finally get there and my nephew is probably seven at this time, and he looks up and says, my brother and I will split a small fat free chocolate. And I was like, who the hell are these children? And how do I get them away if my brother and sister in law immediately I'm like, we walked an hour for the two of you to split a small fat free chocolate? Are you kidding me? I was so upset. Too little. I was like, your uncle's here. What do you want the store? You don't even have to finish it.

[Danielle Fishel]

Yep.

[Will Friedle]

They split a small cup, nothing on top. Nothing of fat free frozen yogurt.

[Danielle Fishel]

I was so depressed. I still needed to spend more time with those children.

[Will Friedle]

Oh my God. Just try walking the streets of Amsterdam, by the way, with two little kids. Like, nope, don't look over there. Don't look over there. Don't look over there. What's that smell? Nothing. Nothing. Don't look over there. Oh, it was amazing. Because you'll walk by like a Coca Cola ad and it'll just be a naked woman, like, buy Coke. And it's like, wait a minute. Okay, this is one. Whoa, whoa. Yeah, it's. But yeah, fat free yogurt.

[Danielle Fishel]

Yogurt dish split.

[Will Friedle]

I was so depressed.

[Danielle Fishel]

We'll share one.

[Will Friedle]

I was like, oh my God. Who are you?

[Danielle Fishel]

What did you get?

[Will Friedle]

The double triple Sunday fudge. Whatever the hell it was, where it was like, I'm eating this and winning a shirt. So sit there and watch me.

[Danielle Fishel]

Welcome to Pod Meats World. I'm Danielle Fishel.

[Will Friedle]

I'm Rider Strong. And I'm Will Friedle.

[Danielle Fishel]

You're both.

[Will Friedle]

I'm both today.

[Danielle Fishel]

Oh, Ryder Strong is not with us because he has finicky Internet.

[Will Friedle]

No Internet today. No Internet.

[Danielle Fishel]

He. He tried. He was on for a few minutes. Things were looking good and then he disappeared and he.

[Will Friedle]

Well, first he froze. The free. The freeze was great. Cuz we were like, it was right when he was going to say rider strong. And he froze and we were like, is he contemplating his name?

[Danielle Fishel]

Is he think.

[Ashley Simpson Ross]

Has he forgotten?

[Danielle Fishel]

Yeah, that is what it looked like. What do you think of when you hear Amazon prime delivery trucks outside your home?

[Will Friedle]

Your favorite streaming shows, of course, but.

[Danielle Fishel]

There is so much more. Whatever you love, that's what prime is.

[Will Friedle]

Prime helps you get more out of whatever passions you're into and it helps you discover new ones.

[Danielle Fishel]

Just today I bought a new makeup remover for my brushes and a few collagen masks that I sleep in. And Amazon prime is perfect for my never ending obsession with beauty products. Not only do I get what I need incredibly fast, I can find myself going down a rabbit hole for all new items I didn't even know existed. Nail brightening treatment? Yes, please. Gre. Green tea clay mask. Yes. Add it to the haul and the.

[Will Friedle]

Fact that Amazon prime also puts hundreds of movies and TV shows right at your fingertips. It's more than just same day delivery. It's a place to explore your passions.

[Danielle Fishel]

From streaming to shopping. It's on Prime.

[Will Friedle]

Visit Amazon.comprime to get more out of whatever you're into okay, can we talk.

[Danielle Fishel]

About the power of a go to outfit? Because when you're juggling school, drop off a dog who needs his flea meds bad and a grocery list you started on the back of your hand. Putting on something that can keep up with is key. So picture me at the park, hair in a claw clip, one shoe untied, granola bar crumbs everywhere and my kids treating the jungle gym like the ropes of a wrestling ring. Then someone walks up to you and says, cute dress and you say, thanks, it's from JCPenney. And that's when you see it. The wait, seriously face. Yeah, JCPenney. Totally underrated style destination. It's packed with stylish, affordable finds for the whole family, especially for the one who keeps it all together. And the deals. I mean, finding a dress that looks amazing and fits your budget? That's a mom win. Worth celebrating. I grabbed the Liz Claiborne Sleeveless A line dress. It's light, it moves with me, and I still looked pulled together while sprinting after a juice box and flip flops. And I picked up a few adorable graphic tees for the boys that fit their growing bodies and their adorable personalities. Already a fan? Then you know. If not, consider this your wake up call. Discover it for yourself. Shop [e-mail] yes jcpenney this Labor Day.

[Ashley Simpson Ross]

Say goodbye to spills, stains and overpriced furniture with washablesofas.com featuring Annabe, the only machine washable sofa inside and out where designer quality meets budget friendly pricing. Sofas start at just $699, making it the the perfect time to upgrade your space. Anibe's Pet Friendly Stain resistant and interchangeable slipcovers are made with high performance fabric built for real life. You'll love the cloud like comfort of hypoallergenic high resilience foam that never needs.

[Danielle Fishel]

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[Ashley Simpson Ross]

Stands the test of time with modular pieces you can rearrange anytime. It's a sofa that adapts to your life. Now through Labor Day. Get up to 60% off site [e-mail] Every order comes with a 30 day satisfaction guarantee. If you're not in love, send it back for a full refund. No return shipping, no restocking fees. Every penny back. Shop [e-mail] Offers are subject to change.

[Danielle Fishel]

And certain restrictions may apply.

[Will Friedle]

You can make a difference in someone's life, including your own with a job in home care. These jobs offer flexible schedules, healthcare retirement options and free training. They also provide paid time off and opportunities for overtime. Visit oregonhomecarejobs.com to learn more and apply. That's oregonhomecarejobs.com.

[Danielle Fishel]

Ah yes, it's the season of Back to school. The scent of sharpened pencils fills the air and your child suddenly has very strong opinions about sneakers. Luckily, Famous Footwear has all the big name brands they're obsessed with Nike, Adidas, Jordan, Crocs, Converse, New Balance, Birkenstock. But now without the big time drama. I used to love Back to School shoe shopping. As a kid I'd strut out of that store like I was walking a red carpet. If that red carpet led to a cafeteria that served square pizza. But now I keep it simple. I skip the checkout chaos and order online, pick up in store or get same day delivery with doordash. It's fast. You can easy and no one ends up crying in the clearance aisle. Not even me. They've got over 830 locations plus in store fit experts who help pick the right size because they know kids feet grow every few minutes. Famous Footwear saves you time, money and sanity and still lets your kid feel like the main character on day one. You don't have to overspend to make it famous right now. Buy one pair of shoes. Get one half off at your local famous footwear store or famous.com see store associate for details. Well, Las Vegas week continues and today we have a banger as we Prep for season seven. It marks Boy Meets World's entry into the year 2000. And as prep, we figured it gets no more Y2K than a 20022003 season of say what? Karaoke filmed at MTV Summer house in the Hamptons. Hosted by Danielle Fishel and a guy named Steven from the Real world and judged by this week's very special guest. It was when I first got to know her, spending one of the best summers of my life with an effortlessly cool pop star driving around, sharing secrets and laughing nonstop, all with the backdrop of a pre paparazzi TRL society. Ah, the good old days.

[Will Friedle]

The good old times.

[Danielle Fishel]

She was just about to release Autobiography, her debut album that would hit number one and go on to sell 5 million copies worldwide. And yet there she was, down to earth, funny, beautiful and for some reason posing for pictures, pretending she had pickles for eyebrows. I have that photo. What?

[Ashley Simpson Ross]

What?

[Danielle Fishel]

I have a great picture with her holding two two pickles above her eyebrows.

[Will Friedle]

So cute.

[Danielle Fishel]

Listen, we had fun. Don't ask what we did. Her and her sister Jessica dominated pop culture at an almost once in a generation level. It's experiencing the highs and lows that came with celebrity at the time. Something I think should be examined then condemned in modern day criticism with words like misogyny and bullying. You see kids, the 2000s got very weird, especially for famous women. We were talking to her just weeks before I Am Me a group of seven shows in Las Vegas at the Venetians Voltaire Theater. It's a return to music for the dedicated mom of three, a celebration for her fans. Those of us who consider songs like Pieces of Me, Lala Boyfriend and the entire Bittersweet World album to be wildly underappreciated jams. Oh, don't believe me? Ask Rolling Stone in the New York Times. Both outlets who've recently admitted that we fumbled what we had with her Young Alanis lyrics at first, then later throwback synth pop. All born too early for its proper credit. But today we will give credit where credit is due. Please welcome to POD meets world. The loveliest spirit and a true survivor. It's Ashley Simpson. Ross.

[Ashley Simpson Ross]

Hi. I'm like, am I doing this right?

[Danielle Fishel]

It was not your fault. We were running like two minutes late.

[Ashley Simpson Ross]

Guys, it's me. Also with technology. I'm so bad at it. I mean, this is me too.

[Will Friedle]

Terrible.

[Ashley Simpson Ross]

It's nice having like a 16 year old son because I'm like, but he's not here right now. He's in Japan. Usually I'm like, what do I do?

[Danielle Fishel]

What is Bronx doing in Japan?

[Ashley Simpson Ross]

He's out there with his dad right now. Like just Pat. He's been out there for a bit.

[Danielle Fishel]

Just living life.

[Ashley Simpson Ross]

Summer trip.

[Will Friedle]

Oh, that's awesome. It's a beautiful place too. I'm jealous.

[Ashley Simpson Ross]

I mean, I need him right now. I'm doing technology things.

[Danielle Fishel]

I know. Hello. FaceTime him. I need you. What time is it in Japan?

[Ashley Simpson Ross]

Oh, I'm like, am I doing this Instagram right? Like, yeah.

[Will Friedle]

She's gonna need his help to FaceTime him though. That's the problem.

[Danielle Fishel]

I know exactly.

[Ashley Simpson Ross]

I don't know. But like, that's the nice thing about having a team.

[Danielle Fishel]

Totally.

[Ashley Simpson Ross]

Now, like, we just saw you at the mall. I had this shirt on. I'm rewearing.

[Danielle Fishel]

I was literally planning when we started our interview to talk about how lovely it is to see you for the first time. And then we ran into each other at the Topanga Mall. At our mall. Where's at our mall?

[Ashley Simpson Ross]

My mall too. Guys.

[Will Friedle]

What are we neighbors? Are we all neighbors?

[Ashley Simpson Ross]

That's how we are neighbors.

[Danielle Fishel]

Yep.

[Ashley Simpson Ross]

We are slime plays for the kids. And you know what is so funny? Here's about, like, how funny life is with Jagger. Didn't realize who you were. And then I told her after, and she was like, oh, my. Oh, my God. Mom, she's carpenter. Yeah.

[Danielle Fishel]

Girl Meets World. Of course. That's, like, in her. In her ballpark.

[Ashley Simpson Ross]

Oh, my God. I was dying. She was like, oh, my God. Can we, like, go back and call her? I was like, jack, you can't see her anytime.

[Danielle Fishel]

We'll do lots of get togethers. We'll do lots of hangs.

[Ashley Simpson Ross]

We're at that Topanga Mall.

[Danielle Fishel]

Do your kids like the mall? The same way we all liked them all when we were teens.

[Ashley Simpson Ross]

It's so funny because I feel like even with my husband, he's like, I've never known somebody who likes the mall. Like, why do you like to go to the mall? Like, thank you. You're going to the mall, and, like, that's where you're taking the kids to the mall. And, like, like, yes.

[Danielle Fishel]

That's what we grew up doing.

[Ashley Simpson Ross]

Yeah.

[Danielle Fishel]

So do mine. So my son started his first day of first grade yesterday, and on the little form thing you fill out, you know what his name is, what school he goes to, what his. What are some things he loves. I said, what do you love? And he said, my mom, my dad, the mall, and everyone in my family. And I was like, great.

[Ashley Simpson Ross]

There's so many opportunities. You can go to the movies, you go to the arcade.

[Danielle Fishel]

You can eat some food. If you're not really that hungry, you. You can stop at the food.

[Ashley Simpson Ross]

You can get a snack.

[Will Friedle]

I like that the mall was higher on the list than his brother.

[Danielle Fishel]

Yeah, brother fell into everyone else.

[Will Friedle]

Everyone else in the family. Yeah.

[Ashley Simpson Ross]

Yeah. He didn't get his. I like him, but nice. The mall is my happy place.

[Danielle Fishel]

Mine, too. Absolutely. And, Ashley, I have been so excited to get you on the podcast. Not just so we could catch up, but because you are essentially doing the music equivalent of our podcast in Vegas. You're at the Venetian revisiting your music career, but instead of a podcast, you're doing it with a whole string of shows. And we are talking to you just a few weeks before your first show. How are you feeling about it all?

[Ashley Simpson Ross]

I'm feeling so good. I'm really excited about the show. I mean, honestly, just being in that room, and I have so many, like, female players now too, which is so fun. And just new players. Revisit that music. And for me to revisit and revisit the things like, I wrote when I was 18, 19, 20. Revisiting that has been so much fun for me. And just, like, bringing it to 25 right now. I'm so excited, honestly. And another thing like that really, like, drove me to. It was my daughter, like, all of a sudden, like, her and her friends were like, hello, hello. Like, doing a little ve and like, I was like, how is this, like, happening? I'm like Pat Benatar to you.

[Danielle Fishel]

You know what I mean?

[Ashley Simpson Ross]

Like, there was like a lamb after me and all that. And then there was like, Pat and.

[Danielle Fishel]

Like, yeah, yes, yes, I know.

[Will Friedle]

I love when I understand the musical references.

[Ashley Simpson Ross]

And, you know, I'm like the older tier.

[Will Friedle]

Oh, God, that's awesome.

[Danielle Fishel]

How did it come together? Who approached you? Did you have to be convinced? Was it your brainchild? How did it come about?

[Ashley Simpson Ross]

I think my husband and I were like, oh, God. Like, you know, I've been wanting to play again and I've been wanting to put music out. And I did a 20 year anniversary anniversary of my first album last year, and I did, like, I just played three songs, and when the three songs were over, I was like, that's it.

[Will Friedle]

Not enough.

[Ashley Simpson Ross]

I wanted to keep going. So this just felt like organic and fun. Vegas is, like, so sexy and close, and it just, like, gives you that vibe where you can be nostalgic. I've seen his mother, Diana Ross, play there. She's amazing. And, like, it's just a place where I think Vegas is, like, open to so many fun things. So for me, it was just like, the right opportunity. And for me, I'm like a person who, like, waits for that door. I'm like, okay, here's an open door and this is the moment. And I can't wait to see what this brings.

[Will Friedle]

Yeah, it's interesting because when we started this podcast, we didn't know what was going to happen either. There's just kind of, okay, we're going to talk about what it was like. We were a certain age and we've got, you know, this. Seven years of our life has been captured, and we can. But then it brought up a whole lot of stuff we didn't expect to be churned up. And you're kind of reliving certain things, not all of it great. Have you noticed that you're kind of going through some of the same emotions as you're going back through your catalog?

[Ashley Simpson Ross]

Oh, my God, yeah. And every interview I get to relive everything. But yes, and also, like, a Lot of, like, great. Like, actually, I met Danielle. We were working. What was it?

[Danielle Fishel]

MTV in the Hamptons?

[Ashley Simpson Ross]

Was it spring break or summer beach house?

[Danielle Fishel]

It was summer beach house. Yes. When the year they brought back. Say what? Karaoke.

[Will Friedle]

Oh, my God.

[Danielle Fishel]

Which I think was like, 2002, 2003.

[Ashley Simpson Ross]

It was. Yeah. Because I hadn't come out with my music. I was writing music, but I didn't come out. Yeah. I was on seventh Heaven.

[Danielle Fishel]

Yeah. And we. Honestly, it's one of my most favorite memories of my entire life is the time Ashley and I got to spend together that summer.

[Ashley Simpson Ross]

We had that time. We had the best time.

[Danielle Fishel]

I don't know about anyone else.

[Ashley Simpson Ross]

That's why, like, seeing you at the mall the other day, I was like, oh, no. Like, you're already doing this. But I was like, oh, yes.

[Danielle Fishel]

Yeah. We just. There. We had such a great time. I don't know what anyone else was doing, but the two of us, we really did. It was like every. It was like every envision you have of what two teen girls released on their own in New York and the Hamptons. Hamptons minus pillow fights. We didn't have any pillow fights, but otherwise. I know. Why didn't we. Why didn't we ruin the W in Times Square?

[Ashley Simpson Ross]

That was, like, the place they would put us all.

[Danielle Fishel]

That's where they put us up.

[Ashley Simpson Ross]

Even when, like, it was like, seventh Heaven, I feel like I was always at the W. Were you guys, too?

[Danielle Fishel]

No, we never got sent to New York.

[Ashley Simpson Ross]

Yeah.

[Will Friedle]

They never sent us anywhere.

[Danielle Fishel]

Well, you immediately sold out all of your first dates when they were announced. And so then they added more. Did you see that coming, or was it a surprise to you?

[Ashley Simpson Ross]

It was a surprise to me. I mean, I. I didn't really know what to expect. For me, I was just like, oh. Like, in general, just to get back to play those songs. And the 25 version of it, which is like, what I've been being in the room enjoying is I'm like, oh, Ashley. Yeah. Because a lot of my lyrics, like, I go through. And every day when I was younger, it was like therapy. I'd go to the studio. Like, my boyfriend broke up with me. I'd go to the studio, write about it. And what people don't do in their music anymore are bridges. And that's, like, your resume. That's, like, your light. That's your. And so, like, every song, like, I have that. And I'm like, you always found it. Even though you were young and going through so much. You know, I feel Like I always was like finding that and I feel like, like as a 40 year old woman, I'm still able to connect that and see so much of that and I'm like, ooh, yeah. Like, yeah, girl, you, yeah, you're proud of, proud of young you, like what? It's so hard because you don't pat yourself on the back at that time.

[Danielle Fishel]

Yeah.

[Will Friedle]

Right.

[Ashley Simpson Ross]

But it's almost like at this age now you can be like, oh, that was really good, Ash. Yeah.

[Danielle Fishel]

Isn't it nice too to be able to look back and give that younger version of you that you were so hard on a nice hug?

[Ashley Simpson Ross]

Be like, I mean, do you do the same?

[Danielle Fishel]

Absolutely. It's like, wow, you were, you weren't that awful. Why are you so. Why were you so hard on yourself, Danielle? Yeah, because like I was so hard on myself.

[Ashley Simpson Ross]

Right.

[Danielle Fishel]

And I look, I look back now.

[Ashley Simpson Ross]

And I'm like, you were doing great.

[Danielle Fishel]

Yes. Look at you go.

[Ashley Simpson Ross]

Look at you go, girl.

[Danielle Fishel]

So, yeah, it's, it's so nice to like, yeah, to feel a sense of.

[Ashley Simpson Ross]

Pride, like a freeing moment, I think. And I can't wait to be there and play the shows. And for me it's just been nice. Like just the testament of like my fans now, you know, know they're all adults that the kids that were like 9 and 11 that came to my show back in the day, they're like grown, grown ups and Demi Lovato and I mean even so that was another moment too because she used to cover my song Lala on her tour and I went and played it with her and I was like, God, that was so much fun and like how much I like respect her as an artist and, and the fact that she was playing, that was so nice. Nice A.

[Danielle Fishel]

That is so.

[Ashley Simpson Ross]

All those moments like led to this, to me to like be here now and I'm so excited. And also my daughter, she's like the one who's like, she came to my rehearsal the other day, she's like, mom, you sound so good and like your face. I was like, cuz she doesn't know that side of me. Just like, yeah, get me this mom.

[Will Friedle]

Yeah, your mom.

[Ashley Simpson Ross]

Exactly. Give me this right now.

[Danielle Fishel]

Well, we have established that everyone is ready for Ashlee simpson Ross in 2025. But I wanted to talk a little bit about your past as well because it is a common trivia question, but I'm not sure everyone knows you were the youngest person ever admitted to the School of American ballet at age 11.

[Will Friedle]

Wow.

[Danielle Fishel]

How did that come about growing up in Texas. How did you then find yourself in ballet?

[Ashley Simpson Ross]

You know, my mom, like, always. My mom's like my best, best friend still. You know my mom.

[Danielle Fishel]

I know your mom. Yes.

[Ashley Simpson Ross]

But she always kind of supported our dreams. And Jessica and I, like, grew up entertaining, which I'm sure you guys did. Yeah, well, yeah, where you're at. And for me, ballet was just something like, I started at such a young age and I took it so seriously. Like, by the time I was in third grade, I was on point, so I was like, like dancing with 17 year olds by the time I was, you know, very young. To Prince Lord.

[Danielle Fishel]

Oh, my gosh.

[Ashley Simpson Ross]

But, you know, for me, I think the. The one great experience about that. So then I would go downtown. I lived in Dallas and I go downtown. I'd audition for all the ballet schools. So, like, then I was, like, accepted, you know, full scholarships to, like, Kirov abt, sab, those things. And then I. I always loved SAB in New York City Ballet, so I went there. But, yeah, I mean, it's like one of those things that's still, like, engraved in my body.

[Danielle Fishel]

Yeah. Well, you mentioned your sister Jessica, who then became a global pop star and a reality TV pop culture phenomenon. How did the takeoff of her career start the trajectory of your career? You started as a backup dancer for her, right?

[Ashley Simpson Ross]

Yeah, me, it's okay.

[Danielle Fishel]

So how did that start shaping your future? And when did the record deal discussion start?

[Ashley Simpson Ross]

Okay, so I did sab. I would do the summers. I was offered the year to go there. And then my family, my sister got signed to Columbia. That the second year I went to sab. It was a summer I went actually, and they were like, oh, you can go all year. And got signed in. My family was like, we're going to move to la. And it was actually funny enough, but that year I was like, oh, you know, like, I love ballet, but I'm not gonna be a ballerina, you know, so they were like, you could go, you can stay. You can go to New York and do school there at Juilliard and go to ballet or you can come with us to la. And I was like, oh, I'm gonna go to la. I'm gonna go to acting classes and I'm gonna like. I. You know, because I also, like, dreamed of, like, theater and acting and just like a different world of stage other than one thing. So I went with my family and they were like, you can dance back up for your sister. And I was her background dancer. Now, mind you, I'm Not a hip hop dancer. So I'm working with all these great dancers, like get down, get low. It's like sometimes I'm a half beat behind and I got it.

[Danielle Fishel]

Yeah, I can't imagine.

[Ashley Simpson Ross]

Ballet dancer.

[Danielle Fishel]

I was gonna say I can't imagine ballet translating super easily to hip hop.

[Ashley Simpson Ross]

I'm great with Moder.

[Will Friedle]

Why is that one girl in the background on point?

[Ashley Simpson Ross]

No, but it was just such a cool experience to have that with my family. And, you know, you guys know that time, it was a time where, like, I felt very, like, like I wanted to cover her and support her as well. Like, the world was just so different with artists and everyone and judgment. Like, oh, the magazines and everybody went. The comments that people felt like they could say about people. I was like, did you just say that about my sister? You know, I felt very, like, protective. But I feel like having that moment, it taught me so much about myself as an artist. So my parents let me have my friend come out on tour with me and guitar tech for the guitar player so I could write my own songs.

[Danielle Fishel]

Oh.

[Ashley Simpson Ross]

So I danced with her until at 16, I. I left and went to seventh heaven and started writing my first album. But having that time, I think really taught me what I wanted, what I needed, you know, like, oh, I will not let you tell me what to do or this label tell me what to do or who I'm supposed to be. So I learned. I mean, I was lucky to have. Yeah, well, big sister that I got to learn from. Yeah.

[Danielle Fishel]

What an incredible education. You know, like a hands on. Right. Right up close look at it.

[Ashley Simpson Ross]

Right.

[Danielle Fishel]

Was there a culture shock for you coming from Texas, moving to la? Like, was there. Did family have a culture shock feeling?

[Ashley Simpson Ross]

Well, where do we moved to? Hacienda Heights and then. Yeah, I mean, I think there was a little bit of a shock. But then I think there was like a group of like Texas people that I was with. Some of them are like, still my best friends to this day. So I think there was a difference and it was, it was different. But then we mostly traveled on. On tour. So that part was just like fun and experiencing like the silliness of that with a bunch of like, girls on tour and what that is. And, you know.

[Danielle Fishel]

So was Seventh Heaven your first acting experience?

[Ashley Simpson Ross]

It. No. What was it? I did like a funny, like one line and hot ch. Or a few lines and hot chicken and nice Seventh Heaven. Yeah.

[Danielle Fishel]

Wow.

[Will Friedle]

I'm so curious. I'm sorry, I'm just so curious because you have a very unique insight in that very rarely do you meet people that have been both in the music industry and the acting industry. And so I'm curious how. It's too big a question to say how different are they? But is there one side of the industry that is, quote, unquote, less toxic than the other? So we keep hearing, like, because I only know the acting side of the, of the industry. And they're always like, okay, well, you know, as young actors, it can be, this can be bad or that can be bad. And then. And we hear people often saying, whoa, man, you should see what the music industry is like. So I'm curious, is. Was it that big a difference being a young entertainer in the. The music side of the industry as opposed to the acting side of the industry?

[Ashley Simpson Ross]

I mean, they are different in different ways. But like I said, like, I, I feel like, yeah, I mean, the music industry at that time was definitely, you know, I had a lot of highs, had a lot of lows, right, Everything for me, I guess it was just that moment of also. And that's where I look back and give myself a hug because I always stayed grounded. I was like, I am, I think being an actress or a singer, actor, anything, it's not letting people dictate what you are or any failure or this audition or that, or this, you know, music or this performance which I've had, but dictating who you are or your self worth. And I think for me, like, like, I don't know what it was inside of me, but I would dig to that and say, I was there, I wrote this, this is about me, this is my life. And you know, you would find that strength within yourself. And I mean, I think they're both tough though, right?

[Danielle Fishel]

Yeah.

[Ashley Simpson Ross]

The seventh Heaven was so nice. I mean, that's like a great family. I had Beverly Mitchell and like, and I was there like writing songs. Like Rachel, Rachel Blanchard, she'd run my lines with me every day and I was there writing songs and they would come to my trailer and listen to like the new song I wrote. And at the same time, I was also filming my reality show, the Ashley Show. So it was like a lot of layers going on.

[Danielle Fishel]

So so many things to keep track of, which, like you said, giving yourself a big hug for the fact that you have always remained authentic for as long as I've known you, no matter what's been going on, you've always just seemed like Ashley. You've always just maintained who you were at your core, even while riding the waves of highs and lows. That no matter what industry you're in, life just throws at you.

[Will Friedle]

Yep.

[Ashley Simpson Ross]

Right. And I mean, I think, like, it's God, hopefully our most important lesson we can give to our children because now it's like social media and everything. Expectations and like, definitely, you know, it's everywhere now.

[Danielle Fishel]

Yes, absolutely.

[Ashley Simpson Ross]

But what I was going to say, though, the other thing about acting was the day that I finished seventh Heaven, because you have to have continuity with your hair and whatnot. I went to CVS and I bought a hair dye box with brown hair and dyed my hair.

[Will Friedle]

Taking the power back. Taking the power back.

[Ashley Simpson Ross]

My video for Pieces of me, my single. And I call everyone. I'm like, I just want you to know I have brown hair and it's from a box that cvs.

[Danielle Fishel]

Did you like the way it turned out? Did you like the brown?

[Ashley Simpson Ross]

I mean, I did. And then I kept going and it was dark. I mean, I don't know. I mean, it was all like doing life in those young ages. You're in your, like almost at that time, like your college years. So it's like apartment you're experimenting, you're coloring your hair, every color you know, you're doing everything and it's all in front of everybody. 1.

[Danielle Fishel]

What do you think of when you hear Amazon prime delivery trucks outside your home?

[Will Friedle]

Your favorite streaming shows, of course, but.

[Danielle Fishel]

There is so much more. Whatever you love, that's what prime is.

[Will Friedle]

Prime helps you get more out of whatever passions you're into and it helps you discover new ones.

[Danielle Fishel]

Just today, I bought a new makeup remover for my brushes and a few collagen masks that I sleep in. And Amazon prime is perfect for my never ending obsession with beauty products. Not only do I get what I need incredibly fast, I can find myself going down a rabbit hole for all new items I didn't even know existed. Nail brightening treatment? Yes, please. Green tea clay mask. Yes. Add it to the haul.

[Will Friedle]

And the fact that Amazon prime also puts hundreds of movies and TV shows right at your fingertips. It's more than just same day delivery. It's a place to explore your passions.

[Danielle Fishel]

From streaming to shopping. It's on Prime.

[Will Friedle]

Visit Amazon.comprime to get more out of whatever you're into.

[Danielle Fishel]

Okay, can we talk about the power of a go to outfit? Because when you're juggling school, drop off a dog who needs his flea meds bad and a grocery list you started on the back of your hand. Putting on something that can keep up with you is key. So picture me at the park. Hair in a claw clip, one shoe untied, granola bar crumbs everywhere, and my kids treating the jungle gym like the ropes of a wrestling ring. Then someone walks up to you and says, says cute dress and you say thanks. It's from JCPenney. And that's when you see it. The wait, seriously face. Yeah, JCPenney. Totally underrated style destination. It's packed with stylish, affordable finds for the whole family, especially for the one who keeps it all together. And the deals. I mean, finding a dress that looks amazing and fits your budget? That's a mom win. Worth celebrating. I grabbed the Liz Claiborne Sleeveless A line dress. It's light, it moves with me, and I still looked pulled together while sprinting after a juice box and flip flops. And I picked up a few adorable graphic tees for the boys that fit their growing bodies and their adorable personalities. Already a fan? Then you know. If not, consider this your wake up call. Discover it for yourself. Shop [e-mail] yes jcpenney this Labor Day.

[Ashley Simpson Ross]

Say goodbye to spills, stains and overpriced furniture with washablesofas.com featuring Anabe, the only machine washable sofa inside and out where designer quality meets budget friendly pricing. Sofas start at just $6.99, making it the perfect time to upgrade your space. Annabe's pet friendly stain resistant and interchangeable slipcovers are made with high performance performance fabric built for real life. You'll love the cloud like comfort of hypoallergenic high resilience foam that never needs.

[Danielle Fishel]

Fluffing and a durable steel frame that.

[Ashley Simpson Ross]

Stands the test of time with modular pieces you can rearrange anytime. It's a sofa that adapts to your life. Now through Labor Day. Get up to 60% off site [e-mail] Every order comes with a 30 day satisfaction guarantee. If you're not in love, send it back for a full full refund. No return shipping, no restocking fees. Every penny back. Shop [e-mail] Offers are subject to change.

[Danielle Fishel]

And certain restrictions may apply. You can make a difference in someone's.

[Ashley Simpson Ross]

Life, including your own, with a job in home care.

[Danielle Fishel]

These jobs offer flexible schedules, health care, retirement options and free training. They also provide paid time off and opportunities for overtime.

[Ashley Simpson Ross]

Visit oregonhomecarejobs.com to learn more and apply.

[Danielle Fishel]

That's oregonhomecarejobs.com Ah yes, it's the season of back to school. The scent of sharpened pencils fills the Air. And your child suddenly has very strong opinions about sneakers. Luckily, famous footwear has all the big name brands they're obsessed with. With Nike, Adidas, Jordan Crocs, Converse, New Balance, Birkenstock. But now without the big time drama. I used to love back to school shoe shopping. As a kid, I'd strut out of that store like I was walking a red carpet if that red carpet led to a cafeteria that served square pizza. But now I keep it simple. I skip the checkout chaos and order online, pick up in store or get same day delivery with doordash. It's fast, easy, and no one ends up crying in the clearance aisle, not even me. They've got over 830 locations plus in store fit experts who help pick the right size because they know kids feet grow every few minutes. Famous footwear saves you time, money and sanity and still lets your kid feel like the main character on day one. You don't have to overspend to make it famous right now. Buy one pair of shoes, get one half off at your local famous footwear store or famous dot com. See store associate for details. So Autobiography, your debut album came out in 2004. As you mentioned, it turned 20 last year. It was five times platinum hit, number one on the Billboard top 200. And it is filled with teen angst. Now, title in mind, was the album a proper representation of who you were?

[Ashley Simpson Ross]

100% okay. And it's so funny because I go autobiography. Well now, you know, you're like, oh, was like autobiography now. Exactly.

[Danielle Fishel]

It changes.

[Ashley Simpson Ross]

But it was at that time because for me, writing it was like every day I'd go in with like my fresh breakup, my fresh like new boyfriend, like this is me, love me for me. And you know, with all those, you know, it was literally like the diary of my life. And having like Kara Dioguardi and John Shanks with me, it was like they were my therapist and we were in this room of like this writing session every day, which was. Yeah, yeah.

[Danielle Fishel]

Well, you were and are very different than your sister Jessica. I saw a recent interview you guys did and for New York magazine and she talked about how you are the cool one, she was the rule follower and you really forged your own path. What was it like for the two of you having each other by your side through the wild ride that was the 2000s.

[Ashley Simpson Ross]

I mean, I think it's like been the, the big biggest blessing. And that interview was so much fun because I was interviewing her, so I did like on her. I'm like okay. Like, trying to study her new album. And I was like. I was like, okay. And I felt so, like, professional about it.

[Danielle Fishel]

Yeah. You were a serious journalist.

[Will Friedle]

I'm going to interview you.

[Ashley Simpson Ross]

So cute. But I think just having each other, where it's this unspoken sisterhood, you know, it's just us. We don't have a brother, a sister. It's just us. And I think it's this unspoken understanding of everything, everywhere we've been and throughout life, you know? And I think just. And we have my mom, who's like, our third.

[Danielle Fishel]

Yeah, the third sister.

[Ashley Simpson Ross]

My mom. Everyone, like, we go to the same nail salon. Everyone's like, is it Tina or Ashley?

[Danielle Fishel]

It's so funny. Do people. Do people tell your mom you guys sound alike? My mom and I know.

[Ashley Simpson Ross]

Yeah. Yeah.

[Danielle Fishel]

My mom and I, too. No matter which one of us is calling, people never know which one of us it is.

[Ashley Simpson Ross]

It's so funny. No, but having Jessica has just, like, been like a lifeline, honestly. Yeah.

[Danielle Fishel]

So great. The Ashley Simpson show was another example of an undertaking totally ahead of its time. It was a reality show launching pad. Chronicling you making music was. Was the show an overall positive experience for you? I mean, you've gone on to do it again with your husband Evan, but did you ever regret putting your teenage personal life on tv?

[Ashley Simpson Ross]

Not. I mean, sometimes, because now Jagger's found it. My daughter.

[Danielle Fishel]

Oh. So just now there's some regret.

[Ashley Simpson Ross]

It's okay, though, because the, like, my best friends on the show, Stephanie and Lauren, they're on the show with me, and they're, like, the godmothers of both my children. And there's so many silly moments. I mean, the only thing that kills me is, like, my voice. I'm like, I am this voice. I'm like, oh, my God, what is this talking voice? It was like, I think, like, naturally hearing the sound of your voice, but then that one really kills me. But I think for me, though, it was so important because it was such a window to my life and what I was thinking, what was changing. And I feel like it was like there had been, like, my sister's show, the Newlyweds, and the Osbornes, and this was, like, kind of the first of that. Kind of, like, making, like, doing, like, an album, but not, like, making a band. Somebody putting.

[Will Friedle]

Yeah, right, right.

[Ashley Simpson Ross]

Just following the process. And also because I've been there during Newlyweds, a lot of the times I'm like, get out of my face.

[Danielle Fishel]

Right.

[Ashley Simpson Ross]

I definitely always had, like, a little. I'm probably, like, much Nicer now than. I just like, felt like I needed to be like, no, right, right. You needed.

[Danielle Fishel]

Yeah. You needed to protect. You felt like everyone there. There's always the possibility somebody's going to try to cross the line. And you were always going to be very quick to be like, I'm not going to allow you to cross the line.

[Ashley Simpson Ross]

Exactly. But then I would always remind myself, it's okay. Be vulnerable. This is you opening up. And so I'm. I do love that. And then Evan and I did a show.

[Danielle Fishel]

I don't.

[Ashley Simpson Ross]

I don't even know what year that was. But then I was like, oh, yeah, that's not for me now.

[Danielle Fishel]

Oh, really? Okay. So not anymore.

[Ashley Simpson Ross]

I have kids. I'm like, no, thank you.

[Will Friedle]

You know, so you talk. You talk about your process and then how it was, you know, when you're doing that show, it's kind of the whole process you're going through. But huge question. How does one write a song? Hmm.

[Ashley Simpson Ross]

Ha. You know, I started writing when I was young, and for me, like, I think it's just like finding the team, the theme. And, like, I would be in my car driving every day. Like, what just happened to me? What? You know, I'm like. I mean, I was dealing with, like, first boyfriends and. Right. You know. Oh. A lot of the times I like to start with the concept. Okay, yeah, Concept. And like, what is that concept? And especially during that time because so many things were new and like, having first boyfriends and first heartbreaks and, you know, God, I had a boyfriend that was like, you look fat. You need to get on the treadmill, you know, get ready for what I'm about to say. I think that there was just so many, you know, feelings and like, for me, it was like every day, like, what, you know, what I was going through. Yeah. So I think you start with the concept, then you get a guitar, and then you just.

[Will Friedle]

Okay.

[Ashley Simpson Ross]

Melodies or, you know, and. And it really depends. Like, every day, I mean, in those sessions it was different. It was like me, John and Kara Diagordy, and we were like an incredible team. So it was like we became family. So it just kind of became like this every day pattern. But I think, like, a writing camp is great as well.

[Will Friedle]

Okay.

[Danielle Fishel]

And with a writing camp is that you and a bunch of other writers together pitching ideas. Like a writer's room.

[Ashley Simpson Ross]

Like, you can like, go into a writer's room. Like writing. Yeah, exactly.

[Danielle Fishel]

Yeah. Okay.

[Will Friedle]

I saw. I saw actual camp. Like, it's. You go to. It's like camp Rock.

[Danielle Fishel]

You do obstacle courses.

[Ashley Simpson Ross]

There's like, I'm just saying, for people. I haven't actually done a writing camp, but, like, I have wrote with different writers.

[Danielle Fishel]

Oh.

[Ashley Simpson Ross]

Like, we are connected. We are feeling each other. This music is going to be in the right place.

[Will Friedle]

Or it always. It's just the whole process fascinates me because I saw a documentary. I forget what it was called, but they were talking about. They were interviewing a bunch of musicians who said, it's. You don't write a song like it's given to you by some other universe. Like, it just pops in.

[Ashley Simpson Ross]

Right.

[Will Friedle]

It just. You don't know where it comes from, where. And it's just if as someone who has no musical talent, it's so fascinating to see.

[Ashley Simpson Ross]

I mean, it comes from when I was, like, younger. Younger would annoy my parents so much. Like, I had, like, my guitar player, this other guitar player, and we would be like, singing like, I don't need you to be my backseat driver. Really loud, like 11 o' clock at night. Which is funny because now in Bronx, my son, he's great at writing and great at playing, but him and his friend definitely play aloud at night. Oh, like the circle of everything.

[Will Friedle]

Karma.

[Danielle Fishel]

So are your kids in the industry? If. If not, if they wanted to be, would you allow them to be?

[Ashley Simpson Ross]

They are not in the industry. I would allow them to be at their own pace.

[Danielle Fishel]

Okay.

[Ashley Simpson Ross]

I would never push it. I would just say I think the most important thing in this age is developing your craft and deciding what you want with it.

[Danielle Fishel]

Okay.

[Ashley Simpson Ross]

I would never, you know, be like, let's please go be on a show. I really want to be a stage mom.

[Danielle Fishel]

You know what?

[Ashley Simpson Ross]

I really want to sit on set and have you roll your eyes at me.

[Danielle Fishel]

Our other co host, who would normally be here, but his Internet is not working today. Writer. His son has started doing some voiceover work and he's been having to drive him around auditions and he's like, how did this happen? I used to be the kid in the backseat not that long ago, and now I'm driving around LA in traffic for my son. It's crazy how it happens.

[Ashley Simpson Ross]

Yeah. But, you know, I think it's like, I mean, I don't know what your thoughts are, but I'm definitely open. I definitely see my daughter. I mean, she takes acting classes she likes, but I think when she. She's ready, you know?

[Danielle Fishel]

Yeah. And as long as she's not knocking down your door begging to do it now, you're not trying to rush it along like you said, let them lead the pace.

[Ashley Simpson Ross]

Get on the stage. Not saying. She's not knocking on the door.

[Danielle Fishel]

Okay, okay. She's. Yeah.

[Ashley Simpson Ross]

Patience.

[Danielle Fishel]

Yes, patience, dear. Patience. Will only has a stepdaughter who is in her mid-30s, so it's a little. She's. I don't think she's gonna change now.

[Will Friedle]

She's. No, she's pretty set in her ways at this point.

[Ashley Simpson Ross]

Point. Yeah.

[Danielle Fishel]

She's a wonderful interior designer, though. If you're looking for an interior design.

[Ashley Simpson Ross]

I always need it now.

[Will Friedle]

So you mentioned that reality isn't for you anymore, but would you ever consider getting back in front of the camera in an acting job?

[Ashley Simpson Ross]

Yes, definitely. And I'd love to do, like, more theater. I did Chicago. I did it on the West End and Broadway and Hollywood Bowl.

[Danielle Fishel]

Were you Roxie Hart?

[Ashley Simpson Ross]

I was Roxy, yeah. But I played it so many different times in my life, which was so fun. Like, the first time I played it in London, I was like, like 22. And then I did it on Broadway when I was 25 after I had had Bronx. And then when I did it at the Hollywood bowl, which was so cool because I just started dating Evan. His mom had a show there the week before, and that's when he first met his mom, Diana Ross. That's the first time I met her was.

[Danielle Fishel]

That's so cool.

[Ashley Simpson Ross]

Yeah.

[Danielle Fishel]

So you met her at the Hollywood bowl the week before you then played the Hollywood.

[Will Friedle]

That's cool. That's cool. Yeah. Yeah.

[Ashley Simpson Ross]

And then I'm playing, like, when I'm doing Vegas. It'll be our 11th year anniversary on the 30th when I have a show. Man, that's amazing. On our 10th, we got that romantic 10 one in. Yes.

[Danielle Fishel]

You got to do something nice for 10. Listen, I want to talk to you about Bittersweet World too, because over the years, it has finally gotten the credit that it deserved. But before I get there, I wanted to talk to you a little bit about the Internet because I have always seen the SNL performance as a real mask off moment for the toxicity that would later become online bullying.

[Will Friedle]

Yep.

[Danielle Fishel]

And we've all said, we've all heard that, like, oh, we've grown a bit as a society. But I wanted to ask you, as a person who has felt the unwarranted wrath of its stupidity, do you think we have grown at all as a society when it comes to understanding that celebrities, bullies, are human beings who have flaws and make mistakes and also are real people?

[Ashley Simpson Ross]

I think it's a different era. You Know, I don't think if it was that moment in this era, would it be that, you know, I think during that time, I mean, the bullying was insane. Insane. And that's what I was saying to you earlier, too, about being a human and being a human that. Oh, like, oh, she did lose her voice. Oh, that doesn't mean she didn't write these songs. And this isn't like her. And, like, we can't go back and see her on tour, which I feel like I was able to do. But then my whole life I did, like, tell people, like. And I was like, what am I trying to tell people? Like, yeah. Oh. But I perform every night. Like, my fans know, and I had to, like, know that in my heart. Like, oh, I'm selling out the Greek. I like, you know, like, I am doing that. And like, yes, I've had ups and downs just like every other human. But I do think it's evolved. But also it hasn't, you know, in some ways, but it's evolved.

[Danielle Fishel]

Okay.

[Ashley Simpson Ross]

But I think it's different now. For us, we had the magazines and this. Now everything's kind of more fleeting. Yeah, that was more like, here it is to be on your shoulders forever. Now everything is, like, a little bit more fleeting and frustrating fast.

[Will Friedle]

Well, we just have less attention spans now, so that's just.

[Ashley Simpson Ross]

Everyone's on the. The phone too much.

[Will Friedle]

Exactly. You got Tik Tok and you've got everything. Anything over 90 seconds and an entire generation isn't going to follow, isn't going to watch. So, yeah. Crazy.

[Danielle Fishel]

Well, Bittersweet World was an album you executive produced yourself, and it really felt like it was your vision.

[Ashley Simpson Ross]

Did it?

[Danielle Fishel]

Was it. How was that album different for you?

[Ashley Simpson Ross]

You, Ah, that album was like, I was just ready to move into something different on that album. And when I listened to it, I mean, it's actually fun because during the Vegas show, I'm playing three of the songs from it. Boys, A Little Miss Obsessive and out of my head. But looking back at it, it's so funny because I. I do wish I would have evolved that album more because some of the songs, I'm like, love, like, where I was going, but I would have, like. But it's funny because this is before. This is 2007. This is before. There's, like, a lot of big artists out that ended up doing that sound, so it was like kind of like the beginning again.

[Danielle Fishel]

You were ahead of your time. You have been ahead of your time.

[Ashley Simpson Ross]

Like, there was some songs like, ooh, when I hear it. I'm like, God, I wish I could have, like, rap that. Or, like, you know, I'd go, but. But I'm so proud of the album because I was taking such chances of something.

[Danielle Fishel]

Yeah.

[Ashley Simpson Ross]

And there are songs that, like, I love, love, love on that album. And then songs that I'm like, oh, I'd like to redo that one. Yeah.

[Will Friedle]

Well, can't you. I mean, has an artist ever done that? If it's. If it's yours, and you're like, you know what I wish I did with this song? Can't you just take it and then just do that?

[Ashley Simpson Ross]

Yeah, I'm sure. I mean, I'm still, like, proud of it, but, like, you know, sonically or things like that, you're like. I mean, I think lyrically it was really cool. So, I mean, just some of it, you're like, well, it was also 2007, like I said it was before. Yeah.

[Danielle Fishel]

Yeah. I mean, you could definitely make the case that. Had you, like, you said, you. You look back and you think, oh.

[Ashley Simpson Ross]

I would have just like, out of my head. And Boys, like, which I'm playing right now, I'm like, these are bops. And be like, oh, that was good. Yeah.

[Danielle Fishel]

Yes. And you enlisted names like Timbaland, Chad Hugo, Kenna, J. Rock, some of the best in the biz. And you made an album that I truly believe was overlooked and helped usher in the 1980s Electro pop sound that basically rules pop music now.

[Ashley Simpson Ross]

That's what I was. Yeah. Inspired by, like, the.

[Danielle Fishel]

Yes.

[Ashley Simpson Ross]

Yeah.

[Danielle Fishel]

And that album was also a catalyst for a 2018 article in the New York Times, where the headline was just, was Ashlee Simpson Underappreciated? And then this year, we saw Autobiography, your debut, picked as number 237 on Rolling Stone's top 250 albums of the 21st century.

[Ashley Simpson Ross]

Damn that.

[Danielle Fishel]

Does any of that feel like. Does that feel redeeming for you? Do you hear that and think, yes, I just. That. That feels good. That. That feels nice.

[Ashley Simpson Ross]

That does feel good. Good, good.

[Danielle Fishel]

As it should.

[Ashley Simpson Ross]

Yes, that definitely feels good. And, yeah, I feel like in those moments and even in that record, it was just kind of going with the things, like, I was inspired by. And, like, I told you, I was definitely, definitely so inspired by the 80s, even from, like, such a young age.

[Danielle Fishel]

Yeah.

[Ashley Simpson Ross]

Getting to play with that and those, like, sounds. And, I mean, even with Autobiography. So, yeah, just. This is all a big pat on our shoulder.

[Danielle Fishel]

It's a big group house.

[Will Friedle]

So you're talking. Because now I'm not hugely musically fluent, but I love 80s music. So it leads me to ask then, what did you listen to growing up? What were your favorite bands when you were little?

[Ashley Simpson Ross]

Okay, so I loved, like, the Pretenders. I mean, me, like, I love Pretenders. Blondie, Debbie Harry, Joan jets, you know, so good.

[Will Friedle]

Cool.

[Danielle Fishel]

So good.

[Ashley Simpson Ross]

Yeah, they were, like, women of strength. Yeah, Like. Yeah, they were just so cool and, like, rocking and.

[Will Friedle]

Yeah, Debbie Harry was hanging out with the Ramones, for God's sakes. I mean, it was awesome.

[Danielle Fishel]

What are you most looking forward to with your Vegas shows?

[Ashley Simpson Ross]

I mean, I'm most looking forward to just playing this set, playing for the fans. The room is so beautiful and sexy, and I'm excited to bring it this, like, fun rock edge and just like myself. And I'm excited to play the songs and, you know, I think just getting there and seeing what the first day feels like, I'm so happy. I have seven shows, and I feel like every show can be different. And I'm looking forward to that.

[Danielle Fishel]

It's so great. I'm sure you have been asked it in every interview, but I know all of our listeners want to know. Do you ever think new music could be in your future?

[Ashley Simpson Ross]

Definitely. I feel like, you know, I've been writing here and there, and I think right now, like, the moment is like, let's enjoy this, you know, the, like, past, now, the future, and see what that opens up, up, you know, for me in my heart, you know, and once, you know, once I'm there, then I'll really know.

[Danielle Fishel]

I love that. That's cool.

[Ashley Simpson Ross]

No, I feel like whatever I do, I still want to take my kids to school.

[Will Friedle]

That's sweet. And to the mall.

[Danielle Fishel]

That's great.

[Ashley Simpson Ross]

And to the mall, to school and the mall.

[Danielle Fishel]

Those are the two places we gotta go as moms, you know?

[Ashley Simpson Ross]

We need Wetzel Pretzel.

[Will Friedle]

I'm gonna be thinking about that all day now.

[Danielle Fishel]

Ashley, it's not far. Will, you can go to.

[Will Friedle]

I know, but it's. It's a big commitment. Commitment.

[Danielle Fishel]

Ashley, if you could go back as you're prepping for these anniversary shows, and you could tell young Ashley one thing. What would you tell young Ashley? 20 years ago, I would just look.

[Ashley Simpson Ross]

At myself and be like, you are doing good.

[Danielle Fishel]

Yes. You're doing great.

[Ashley Simpson Ross]

Yeah. Because I think so much, you know, so even having that dancer background and everything, we just, you know, beat ourselves down. And just to look at yourself and say, wow, like, you are doing so good. Look at yourself.

[Danielle Fishel]

Yeah, that makes me so happy. I'M so grateful you spent your time with us this morning. I'm so excited for your Vegas residency. I love you so much. It was so great to see you. I want to come see your show. I also want to see you again at the mall. We also are neighbors. We need to get our kids together and just hang out. I'd love to get to know your husband better as well. So, yeah, let's.

[Ashley Simpson Ross]

Please, let's do it.

[Danielle Fishel]

Let's do it. Ashley, thank you so much for joining us.

[Ashley Simpson Ross]

Thank you. Thank you.

[Will Friedle]

Bye.

[Ashley Simpson Ross]

Bye. Bye.

[Danielle Fishel]

Isn't she great?

[Will Friedle]

She's amazing. She's amazing. And it's. It's one of those things where I don't know her music all that well. So I keep hearing you and Jensen talking about kind of the underrated songwriting and all that stuff.

[Ashley Simpson Ross]

I just.

[Will Friedle]

I gotta go listen. I gotta. I gotta at some point realize, apparently there's music after 1991.

[Danielle Fishel]

Yes. And Will, just like when you were like, I don't think I'm gonna know very many of the Backstreet Boy songs. And then when you're sitting there and you're at the Sphere show and you're listening, you're like, you know what? I know significantly more of these than I thought. And on top of that, I like significantly more of these than I thought I would like. I actually have a feeling you would very much enjoy Ashlee Simpson music. I really do. I know your music musical taste enough. I think there's quite a bit that you would really like.

[Will Friedle]

I don't know if it's anything like Alanis Morissette, but Jagged Little Pill is one of my favorite albums of. I used to listen to that just on repeat. So, yeah, no, she's super cool.

[Danielle Fishel]

You gotta listen to Bittersweet World. You'd like it. Yeah.

[Will Friedle]

All right.

[Danielle Fishel]

Check out Bittersweet.

[Will Friedle]

But I'm not doing anything until I get a Wetzel's Pretzel. Now, unfortunately, that's my day. Ashley. Thank you.

[Danielle Fishel]

Oh, we're sorry, everyone. That writer wasn't here today. Internet can be fickle. Unless you live in our little tiny spot of the San Fernando Valley. So, yeah, I guess. Who knows what happened? But we'll catch up with him later. And. And anyway, thank you all for joining us for this episode of Pod Meets World. As always, you can follow us on Instagram, podmeatsworld show. You can send us your emails. Podmeatsworldshowmail.com and we've got merch.

[Will Friedle]

We miss you, Ryder. Merch.

[Danielle Fishel]

Podmeetsworldshow.com we love you all. Pod Dismissed Pod Meets World is an iHeart podcast produced and hosted by Danielle Fishel, Will Friedle and Rider Strong, executive producers Jensen Karp and Amy Sugarman, executive in charge of production Danielle Romo, producer and editor Tara Sudbaksh, producer Matty Moore, engineer and Boy Meets World superfan Easton Allen. Our theme song is by Kyle Morton of Typhoon. Follow us on Instagram odmeatsworldshow or email us at podmeatsworldshowmail.com hey, it's Ryan Seacrest.

[Will Friedle]

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[Danielle Fishel]

You know, I never realized how much better I treat my dog than myself.

[Will Friedle]

Really? Does your dog eat Oreos with every meal and get massages when he stays at hotels?

[Danielle Fishel]

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[Will Friedle]

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[Danielle Fishel]

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[Will Friedle]

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[Danielle Fishel]

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[Will Friedle]

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[Danielle Fishel]

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[Will Friedle]

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[Danielle Fishel]

So if you're not a member yet, join for free online or in store and start saving.

[Will Friedle]

Visit your local CVS store or cvs.com extra big deals to shop this week's Deals. This episode is supported by Belvita.

[Danielle Fishel]

Okay, let me ask you a question. What is the key to having a productive morning?

[Will Friedle]

It's breakfast, right?

[Ashley Simpson Ross]

Yes.

[Danielle Fishel]

And that leads to another question. Who here has time for breakfast?

[Will Friedle]

I know I don't.

[Danielle Fishel]

Thankfully there is always time for some Belvita breakfast biscuits, a little fruit, and a latte.

[Will Friedle]

It's the fuel you need to make the most of your morning. And they're so convenient. They fit right in your routine.

[Danielle Fishel]

With Belvita, you can juggle busy mornings with a positive attitude.

[Will Friedle]

Pick up a pack of Belvita at your local store today.

[Ashley Simpson Ross]

Please welcome aboard the Johnson family.

[Will Friedle]

The whole fam's here for the Disney Cruise. So you know, we came to play. And listen, the adults are gonna have a ball. First we're chilling in the infinity pool, onto massages at Sense's spa, then gliding into Star Wars Hyperspace lounge for a toast. We're even gonna kick back with Mickey.

[Danielle Fishel]

On Disney's private island.

[Will Friedle]

That's how we get down, cuz. Disney Cruise Line is where we came to play.

[Danielle Fishel]

This is an iHeart podcast.