Zach Sang Show

Ryan Cabrera Talks 'On The Way Down' 20th Anniversary, "True," and the Early 2000s

May 23, 2025
Ryan Cabrera, a musician and TV personality known for his hits in the early 2000s, dives into his journey from a Texas bar performer to a pop culture staple. He reminisces about his time on The Ashlee Simpson Show and the whirlwind of fame in an era marked by paparazzi and evolving media scrutiny. Ryan shares tales about Elvis's ring, his unique hair tips, and how reality TV transformed the music landscape. With a humorous nod to Y2K fashion and anecdotes of celebrity encounters, he reflects on maintaining artistic integrity amid commercial pressures.
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ANECDOTE

Creative Anniversary Celebrations

  • Ryan Cabrera and his wife throw elaborate anniversary parties, including a recreated 90s/2000s prom and an adults-only cruise they call the "shit show."
  • These events are ways to celebrate love and connect with friends in unique and memorable ways.
INSIGHT

Pre-Social Media Real Connections

  • Pre-social media, people engaged in direct, meaningful interaction, creating authentic connections during hangouts and music jams.
  • Nowadays, phones often distract from real-life communication, which cultivates a less genuine social atmosphere.
ANECDOTE

TRL Era and Artist Perseverance

  • Ryan Cabrera fondly recalls the era of TRL and paying dues by touring and auditioning directly for label executives.
  • He values this time as it taught perseverance and authentic artistic development distinct from today's social media metrics.
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