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

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.

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)

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)

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

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.

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.

Summary by Pod Meets World Podcast Summarizer – August 2025