Today we talk to Alan Cross, a legend in the music world and the voice behind The Ongoing History of New Music—a show that’s been shaping how we understand music for over 30 years.
If you grew up loving music, there’s a good chance Alan helped you make sense of it—connecting the dots between artists, movements, and moments that changed everything. But this conversation isn’t just about looking back. It’s about how dramatically music has changed… and what that means for all of us.
We get into everything—from the explosion of alternative rock in the early 90s, to the moment Napster flipped the entire industry upside down, to why music today feels so different than it did when we were growing up. Alan shares what we’ve gained, what we’ve lost, and why the future of music might be more fragmented—and more confusing—than ever.
This felt like a masterclass in music, culture, and how technology quietly reshapes the things we love.
Please enjoy, Alan Cross.
Key Takeaways
- The Power of Storytelling in Music: Alan’s success comes from making music feel human—turning songs into stories that pull you in, even if you didn’t think you cared about the artist.
- Why the 90s Changed Everything: The rise of alternative rock wasn’t random—it was the result of cultural shifts, new data (SoundScan), and a wave of artists ready to redefine the industry.
- Napster’s Ripple Effect: What seemed like a side experiment in file sharing ended up dismantling the traditional music business—and the industry never fully recovered.
- Streaming Changed How We Value Music: With everything available instantly and cheaply, music lost its financial value—even though its emotional impact remains.
- Algorithms Are Limiting Discovery: Instead of expanding our taste, streaming platforms often trap us in familiar sounds, making it harder to discover something truly new.
- From Tribes to Playlists: Music used to define identity and community. Today, younger listeners mix genres freely, shifting music from a social signal to a personal experience.
- The Death of Mystique: Social media has erased the distance between artists and fans, removing the mystery that once made rock stars feel larger than life.
- The Future is Fragmented: With thousands of micro-genres and endless choice, music is becoming more personalized—but also harder to navigate and share collectively.
Connect with Bob Mathers
The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/
Alan’s website: https://www.ajournalofmusicalthings.com/
Ongoing History of New Music Podcast: https://curiouscast.ca/podcast/126/ongoing-history-of-new-music/
Uncharted: Crime and Mayhem in the Music Industry: https://curiouscast.ca/podcast/1296/uncharted-crime-and-mayhem-in-the-music-industry/
CFNY: The Spirit of Radio documentary: https://www.ajournalofmusicalthings.com/the-cfny-the-spirit-of-radio-documentary-is-coming-to-theatres/
