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Home Entertainment

Ryan Cabrera Marks 20 Years of ‘On the Way Down’ With Star-Studded Video

by DigestWire member
November 12, 2025
in Entertainment
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Ryan Cabrera Marks 20 Years of ‘On the Way Down’ With Star-Studded Video
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Ryan Cabrera is celebrating a major career milestone with a very special project.

Us Weekly can exclusively reveal that the singer has released a brand-new music video for his star-studded “On The Way Down” 20th Anniversary single.

“We’re in the studio, and we knew we wanted to do a reimagined version of the song,” Cabrera, 43, exclusively shared with Us before the music video was released on Wednesday, November 12. “How do we celebrate it without just doing the same old thing? We have to make it different. It can’t just be the same. But we also don’t want to go too far away from the original.”

What came next was an epic collaboration with a group of artists who Cabrera referred to as the “TRL all-star alums.”

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Backstreet Boys member AJ McClean, ‘NSync’s Joey Fatone, Drake Bell, Walk the Moon’s Nick Petricca, Taylor Hanson and Nash Overstreet lent their voices and talents to create an epic collaboration on a song that changed Cabrera’s life forever 20 years ago.

“We put together a team. You got the boy bands, the rock stars, the emo stuff. It was definitely a smorgasbord of eclecticness of artistry and creativeness, and they made the song what it was,” Cabrera said. “I remember being like, ‘Don’t do what you’ve heard. Don’t do what I would do. Do what you would do on this song.’ And I think they had fun with it too.”

Nearly 20 years ago, music fans fell in love with “On the Way Down” thanks to its sweet lyrics and a catchy chorus. The track was the reason the then-21-year-old singer-songwriter landed a record deal.

The track peaked at No. 15 on the Billboard Hot 100 and No. 4 on the TRL chart. The original music video included Cabrera’s then-girlfriend Ashlee Simpson Ross.

Ryan Cabrera Celebrates 20 Years of On the Way Down With Star-Studded Anniversary Video
Ryan Cabrera Jason Koerner/Getty Images

“I’m very fortunate that this song for some reason gets played still in like the most random place, whether it be grocery stores, Home Depot, Walgreens, Chili’s, Applebees, whatever your neighborhood grill and bar is,” he joked. “I’ll get a bunch of messages from friends all the time where they’ll be at the airport, and they’ll be like, ‘You hear it, right? I’m at the airport.’ For a song that came out, you know, 20 years ago, to still be popping up in all these random spots? That’s pretty cool for me.”

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These days, Cabrera continues making and recording new music. He recently wrapped the Pop 2000 tour with special guests O-Town, BBMAK and LFO.

When he’s not traveling across the country, Cabrera enjoys being at home with his wife, Alexa Bliss, and their 23-month-old daughter, Hendrix.

“It’s all just so new,” he told Us about his family life. “I’ve loved playing music, I love being on tour, but I kind of know what that’s like. I know what to expect. I try to make every concert still different and fun, and change it up every day, but I’ve been doing that for 25 years. Being a dad, being a husband, is still something that I try to work to be better at every single day, and that, to me, is still being creative.”

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