Early-Aughts mainstay Ryan Cabrera first hit the pop culture consciousness as Ashlee’s boyfriend on The Ashlee Simpson Show, but he was grinding as a musician way before Simpson’s dad Joe plucked him from obscurity, performing at a Hard Rock Cafe in Dallas, Texas. He joined us in the studio for the first time to reminisce about his beginnings, his experience on The Ashlee Simpson Show, 20 years of his breakthrough, Johnny ‘Goo Goo Dolls’ Rzeznik-produced debut LP Take It All Away, and coming of age (and fame) without cellphone photography, while intrusive paparazzi and toxic bloggers (hai Perez Hilton!) were on the rise.

The 42-year-old, uber-friendly artist also lifts the lid on how reality TV works now versus then, along with insights into his trademark hair, the Pop 2000 Tour, owning one of Elvis’s rings, recreating proms, and his meet-cute with wrestling icon Alexa Bliss — with whom he shares a daughter. Did Courtney Love really try to make out with him? What he actually thinks about Y2K fashion, and so much more.

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