Vault: Interview Jessica Simpson

Summary

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The Bert Show - Vault: Interview Jessica Simpson (October 28, 2025)

Main Theme & Purpose

This special "Vault" episode of The Bert Show revisits an archival interview with singer Jessica Simpson, recorded during a pivotal moment in her career and personal life. At the time, Jessica and then-boyfriend Nick Lachey were on a break, just months before their engagement. The conversation dives into Jessica’s evolving image, her family dynamics, her shyness, and the realities of navigating fame and rumors.

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Key Discussion Points & Insights

1. Jessica's Evolving Image and Confidence

• Wardrobe & Personal Growth: The interview kicks off with a look at a racy photo of Jessica, prompting discussion about her changing fashion and self-assurance.
  • At 21, Jessica reflects on growing up in the public eye and how she’s matured since her debut at 17 (03:23).
  • She candidly admits, “I would not wear that walking down the street because I’m not confident enough. It’s fine in a photo shoot when I know that things can be airbrushed.” (03:32)
• Stage vs. Real Life: Despite being a public figure, Jessica emphasizes her natural shyness outside of performance.
  • “I’m super shy, like… I’m like in big jeans and a big sweatshirt, my hair pulled back… I don’t know. I’m really shy.” (03:48)
• Photo Shoots: Jessica addresses the reality of modeling for magazines.
  • “You get in your own world. You know, they turn on music… I don’t really like doing photo shoots that much anymore. At first, it was fun, but now it’s like—it takes forever.” (04:28)

2. Family Influence and Support

• Firm Parental Presence: Jessica credits her parents—her mom as stylist and her dad as manager—for keeping her grounded and guiding her career decisions.
  • “My mom’s one of my stylists... I can’t go shopping without my mom. Mom would have never let me arrive here today in this outfit.” (05:09-05:29)
• Sibling Bond: Her younger sister Ashlee is one of her dancers and is set to branch out on her own.
  • “She’s starting to do her own thing. She’s getting into singing and acting and stuff.” (05:38)

3. Relationship with Nick Lachey

• In a Relationship Limbo: When asked about her relationship status, Jessica is honest about the uncertainty.
  • “I don’t know right now… I love him, I do… but we’re not really… we’re not together as of right now.” (06:31)
• Continued Connection: They still talk every day, and Jessica is hopeful about their future.
  • “I kind of feel like… when all’s said and done… oh, definitely.” (06:46-06:49)
• Life Changes: She traces the need for independence back to turning 21.
  • “Six months ago, I felt like I needed it... I guess it was like turning 21 and wanting to be independent.” (06:51)

4. Navigating Fame & Rumors

• Dealing with the Tabloids: Jessica no longer reads press about herself due to previous hurtful comparisons.
  • “I just don’t even read it anymore because there’s no point... I just do what I do.” (07:21)
• Being a Celeb in the Spotlight: Early on, being in tabloids was exciting, but now she avoids the negative (07:42).

5. Fan Experiences

• Freakiest Fan Encounter: Jessica recounts a story about a fan spelling her name with flowers in a garden below her condo, which she found unsettling.
  • “I was like, you know, what if they have like a telescope or something…?” (08:53)

6. Career Highlights

• New Album & Collaborations: Discussion transitions to her then-current album "Irresistible," including working with Atlanta artists Jermaine Dupri and Bow Wow, and her upcoming duet with Marc Anthony.
  • “So third single is going to be my duet with Marc Anthony…It’s called ‘There You Were.’” (09:20-09:24)

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Notable Quotes & Memorable Moments

• On growing up in the industry:
  “She’s just older… and her jeans are lower.” – Interviewer (03:24)
• On confidence:
  “I’m super shy, like… I don’t know. I’m really shy.” – Jessica Simpson (03:48)
• On parental influence:
  “My mom’s one of my stylists… I can’t go shopping without my mom.” – Jessica Simpson (05:10)
• On her and Nick’s relationship:
  “I love him, I do… but we’re not really… we’re not together as of right now.” – Jessica Simpson (06:31) “I kind of feel like… when all’s said and done… Oh, definitely.” – Jessica Simpson (06:46–06:49)
• On reading tabloids:
  “I just don’t even read it anymore because there’s no point… I just do what I do.” – Jessica Simpson (07:21)
• On the oddest fan gesture:
  “They spelled out Jessica in their flower bed with their flowers.” – Jessica Simpson (08:00)
• On performing and her music:
  “Third single is going to be my duet with Marc Anthony. It’s called ‘There You Were.’” – Jessica Simpson (09:20–09:24)

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Important Timestamps

• 02:15 – Introduction to context: Jessica and Nick on a break
• 03:23 – Jessica discusses her evolving image and confidence
• 03:48 – On stage vs. real life shyness
• 04:28 – Experiences with photo shoots
• 05:09–05:38 – Role of family in her career
• 06:19–06:49 – Jessica’s relationship status with Nick Lachey
• 07:21 – Addressing the impact of tabloids
• 08:00–08:53 – Recounting her “freakiest” fan experience
• 09:12–09:24 – New music and collaborations

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Conclusion

This classic interview offers a candid snapshot of Jessica Simpson’s mindset during a formative period. Listeners gain insight into her personal growth, vulnerability behind the celebrity image, the challenges of young fame, and her unfiltered take on love, family, and fandom—with genuine moments that remain engaging years later.

Transcript

[Jeff Bridges]

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[Dana]

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[Jeff Bridges]

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[Dana]

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[Podcast Host]

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[Dana]

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[Interviewer]

You heard them.

[Jeff Bridges]

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[Dana]

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[Podcast Narrator]

It's the birth show once again. One of the great things about listening back to these interviews with celebrities is that they're at a certain place in their life. And when we brought Jessica Simpson in at the time, her, her and her boyfriend Nick Lachey were taking a big time break. Now, three months after that, they got engaged. But pretty interesting to hear what she had to say about him before the engagement even happened.

[Interviewer]

Now, your record guy just handed me this picture.

[Jessica Simpson Interviewer]

Yes.

[Interviewer]

Have a look at this, Melissa.

[Jessica Simpson Interviewer]

Let me take a look at that.

[Jessica Simpson]

I'm definitely not wearing that right now.

[Interviewer]

Now, that picture, if you could paint. Can you paint a picture, Melissa?

[Jessica Simpson Interviewer]

Let's see. We. You have low cut jeans. I assume this is denim, kind of frayed at the top. And you know, when I look at the top, it's, it's, you know, you, you see your stomach and it's more of like a native American feel, you know? You know what I mean? It's kind of like a Pocahontas top. And Jeff, is there anything you want to add to that?

[Interviewer]

Yeah, there's. There's a belly button there, and it's.

[Jessica Simpson]

A, there's a value button.

[Interviewer]

Yeah, it's there. Now, this isn't the same Jessica Simpson that was around a couple years ago.

[Jessica Simpson]

She's just older.

[Interviewer]

She's older and her genes are lower. Is that what happens when you get older?

[Jessica Simpson Interviewer]

Yeah, Exactly.

[Jessica Simpson]

I was 17 years old when I first came out. You know, I'm 21. You know, I would not wear that walking down the street because I'm not confident enough. Like, it's fine in a photo shoot when I know that things can be airbrushed and.

[Interviewer]

What do you mean you're not confident enough? You get up on stage in front of thousands of people and you sing.

[Jessica Simpson]

I'm super shy, like, being like. Like you see me right now, I'm like in a big jeans and a big sweatshirt, my hair pulled back. Like, I. I don't know. I'm really shy.

[Jessica Simpson Interviewer]

So you're super shy. Now, does that play a role when you go out on stage like Jeff was talking about?

[Jessica Simpson]

Or I'm a different person out on stage, not really like a different person. I'm still me, but. But I definitely have a lot more confidence for some reason now like in.

[Jessica Simpson Interviewer]

This photo shoot, like, and I'm always curious about this when, when stars have to do photo shoots, like for this or, like, cover of magazines or whatever. And let's say, you know, when you're shy, I don't. I can't see me trying to do a sexy pose for photographers. You know, in.

[Jessica Simpson]

You know, you kind of get your own world. I know.

[Jessica Simpson Interviewer]

Yeah. So how is it? How do you what?

[Jessica Simpson]

You know, they turn on music, different kinds of music. You just kind of get in your own world. Like, you know, I don't really like doing photo shoots that much anymore. Like, at first it was fun, but now it's, like. Takes forever.

[Jessica Simpson Interviewer]

Is it like when you see the movies, like.

[Podcast Host]

Yep.

[Jessica Simpson Interviewer]

Yeah, Baby pal for me, baby.

[Dana]

That's great, Jessica.

[Jessica Simpson Interviewer]

That's good. Yeah, keep that. Keep that.

[Jessica Simpson]

Yeah, it's exactly like that.

[Podcast Host]

Really?

[Jessica Simpson Interviewer]

Yeah.

[Interviewer]

What was the first time? Because there had to be a first time that one of your PR people or your stylist or somebody came to you with this outfit and said, let's try this one.

[Jessica Simpson]

I was like, oh, no. And, you know, they always try to encourage you. And, like, I worked out a ton before that video shoot, so.

[Interviewer]

Sure, yeah, there's no pressure there with that outfit. You're okay. And then. What about mom and dad, though?

[Jessica Simpson]

Mom and dad are. They're actually not with me right now. They're not on the road with me right now, but normally they are. My mom's one of my stylists. She did my whole tour. And I can't go shopping without my mom. Cause my mom always knows what looks best to me. Like, I'm not good. You know what I mean? Like, I arrived today. My mom. Mom would have never let me arrive here today in this outfit.

[Interviewer]

Really.

[Podcast Host]

I'm rebelling.

[Interviewer]

Mom and dad are away. I'm getting nuts. I'm wearing a sweatshirt.

[Jessica Simpson Interviewer]

Yeah. And my jeans over my navel. No, my.

[Jessica Simpson]

My parents are super involved in what I. Everything that I do. My dad's my manager. My little sister is one of my dancers. She only has one more show with me because she's. She's starting to do her own thing. She's getting into singing, and she's doing lots of acting and stuff.

[Interviewer]

Really? That's cool. How many. How big is your family?

[Jessica Simpson]

Just us four.

[Interviewer]

Your mom, dad, you and little sister.

[Jessica Simpson Interviewer]

Now, I read somewhere you have a pet pig. Is that correct?

[Jessica Simpson]

Well, Nick adopted a pig for me for one of my birthdays. Basically, he saved it from becoming bacon. It's not like I used to have a pet pig, but it uprooted our backyard so I couldn't keep it.

[Jessica Simpson Interviewer]

Okay.

[Jessica Simpson]

And then we just Decided to adopt one.

[Jessica Simpson Interviewer]

And more than one pig.

[Jessica Simpson]

Yeah, I've had one more than one.

[Interviewer]

So what's the deal with you?

[Jessica Simpson]

Her name's Brutus.

[Interviewer]

Are you. Are you and Nick, are you guys together? Are you just exchanging pigs? Are you apart? What's the.

[Jessica Simpson]

I don't know right now.

[Podcast Narrator]

Really?

[Interviewer]

Yeah.

[Jessica Simpson]

Like, I don't know. I love him. I do. Like, I can't help it. But we're not really. We're not together as of right now.

[Interviewer]

That's kind of a bummer.

[Jessica Simpson]

But we still talk every day and, like, I don't know, it kind of feels like we think you're gonna end.

[Interviewer]

Up like, it when all said and done.

[Jessica Simpson]

Oh, definitely.

[Knox]

Really?

[Jessica Simpson]

Yeah.

[Interviewer]

You guys are just doing your whole space thing?

[Jessica Simpson]

Yeah, Well, I don't know. For some reason, like, six months ago, I felt like I needed it, you know, I guess it was like turning 21 and wanting to be independent and.

[Interviewer]

The genes are getting lower.

[Jessica Simpson]

And they get lower.

[Interviewer]

Is it. What's it like when you, like, you know, you and Nick, you guys have an argument or whatever, you decide you need your space or whatever it is, and then you pick up that Inquirer or the Star or something like that, and they're like, there it is. Do you read that to see if they're accurate? Do you just ignore it?

[Jessica Simpson]

I don't. I don't really read, like, stuff about me anymore just because it used to. Like, on my last record, it used to really get at me, like, all the comparisons and all the this and that. And I just don't even read it anymore because there's no point, you know, I just do what I do and try to do the best that I can.

[Interviewer]

Did you ever, like, in the beginning was, like, cool, I'm in the Inquirer. Like, it was a cool.

[Jessica Simpson]

Of course. I mean, I love to be in magazines and, you know, that's when you really feel like things are going good.

[Jessica Simpson Interviewer]

You know what I mean?

[Jessica Simpson]

When you're being talked about, of course. But I just don't always like to hear the bad stuff.

[Interviewer]

What's the most freakish thing someone has done to meet Jessica Simpson?

[Jessica Simpson]

Well, actually, I have to tell you one thing that's pretty freaky. Like, one weird, weird thing is that I live in Los Angeles right now, and I live on the 16th floor of a condo complex type thing, and I have this big terrace. And we were out. Me and some of my friends were out on the terrace one morning looking over or whatever, and there's a house below the building. And it has. They spelled out Jessica in their flower bed with their flowers. So you, like, look over and you see this big Jessica, you know? So that's just like, come meet me, Jessica. You know what I mean? Or like, they wanted to maybe freak me out or something like that.

[Interviewer]

So I'm guessing we had to have.

[Jessica Simpson]

Somebody go check that out.

[Interviewer]

So I'm guessing you probably said, I bet that guy who did that is pretty freaking hot. So I'm. So you threw out.

[Jessica Simpson]

Well, I got scared because I was like, you know, what if they have like a telescope or something and they can look up in my place?

[Interviewer]

Oh, yeah. Once they start messing with their garden, you want to run the other way. So we started to talk about the. The album. The album's irresistible first single was irresistible. And you did. You did a little something with Jermaine Dupree and Bow Wow right here from Atlanta. So that was cool.

[Jessica Simpson]

Yeah, it was really.

[Interviewer]

And then the. The new single, Little Bit. Little Bit is going to radio right now, right?

[Jessica Simpson Interviewer]

Right now.

[Interviewer]

Excellent.

[Jessica Simpson]

So third single is going to be my duet with Marc Anthony.

[Interviewer]

Which one's that?

[Jessica Simpson]

It's called There youe Were.

[Interviewer]

Oh, yeah, look at that. It says duet with Marc Anthony on it. I promise you, Jessica, we will play every one of these songs a million times.

[Jessica Simpson]

Well, thank you so much because you've.

[Interviewer]

Been such an awesome guest. Thank you so much for coming in.

[Jeff Bridges]

It's the Vert show. Morning, Zoe. Got donuts.

[Dana]

Jeff Bridges, why are you still living above our garage?

[Jeff Bridges]

Well, I dig the mattress and I want to be in a T mobile commercial like you. Teach me. So, Dana.

[Dana]

Oh, no, I'm not really prepared. I couldn't possibly at T Mobile get the new iPhone 17 Pro on them. It's designed to be the most powerful iPhone yet and has the ultimate pro camera system.

[Jeff Bridges]

Wow, impressive. Let me try. T Mobile is the best place to get iPhone 17 Pro because they've got the best network.

[Jessica Simpson Interviewer]

Nice.

[Dana]

Je free.

[Interviewer]

You heard them.

[Jeff Bridges]

T mobile is the best place to get the new iPhone 17 Pro on us with eligible traded in any condition. So what are we having for launch?

[Dana]

Dude, my work here is done.

[T-Mobile Announcer]

The 24 month bill credits on experience beyond for well qualified customers. First tax and 35 device connection charge credit send and balance due if you pay off earlier. Cancel Finance agreement. IPhone 17 Pro 256 gigs $1099.99 A new line minimum 100 plus a month plan with auto pay plus taxes and fees required. Best mobile network in the US based on analysis by Oaklove speed test intelligence data 182025 is it t mobile.com hi.

[Knox]

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