Ryan Cabrera Breaks Down HIs 20th Anniversary Version of ‘On the Way Down’ (Exclusive)

In the early aughts, Ryan Cabrera was seemingly inescapable. From being one of the earliest reality TV stars on The Ashlee Simpson Show to the indelible impact of his 2004 debut album Take It All Away to his signature voluminous hair, the Dallas-born singer-songwriter was everywhere.

But it was really his debut single “On the Way Down” that became the initial catalyst for his success. The anthemic pop-rock track, featuring lyrics about finding someone or something that makes you a better version of yourself, peaked at No. 6 on Billboard’s US Adult Pop Airplay chart and No. 4 on the publication’s Pop Airplay chart.

In honor of the song’s 20th anniversary, Cabrera, now 43, revisited the song — this time with a few pop legends, including NSYNC’s Joey Fatone, Backstreet Boys’ AJ McLean, Taylor Hanson, Walk the Moon’s Nicholas Petricca and Drake Bell to put a new twist on it. “[It’s] just all friends [I’ve made] along the way, [and] I’m a fan at the same time of all of my friends as well,” he says.

Alongside the track, he wanted to craft a nostalgic visual. “We wanted something that seemed like a home video, like if you had a VCR camcorder back in the day,” he says. “Not that that’s what was around in 2004 when the song came out. We had those little tiny flip phones or the Samsung Trio or a Blackberry, but it wasn’t getting good video.”

In an exclusive interview with PEOPLE, Cabrera opens up about how the 20th anniversary rendition of the track came together, how Goo Goo Dolls’ Johnny Rzeznik helped make “On the Way Down” a hit and being an early reality TV star. 

PEOPLE: How did the 20th anniversary version of “On The Way Down” come together?

RYAN CABRERA: We wanted to do something special for the 20th anniversary, and me and the producer were in the studio working on something else. He was like, ‘Dude, we should do a different version of the song.” Originally, it was just going to be my new take on this song, but we were like, “What if we did a modern day version of it?”

We were trying a bunch of different versions. At some point, it became an EDM song at 128 [BPM], which was like, “Is this cool?” And then the producer’s wife came in, and she’s like, “Yeah, that’s not cool.” We went back to the drawing board. At the time, a buddy of mine — Nick from Walk the Moon — was texting me about something else, and that sparked something. He swung by the studio, [we] put him in the booth, and he started with a very Walk the Moon chant, and that sparked what the new version was.

At that point we were like, “Yo, this would be cool if you just got a bunch of your friends to come collaborate and put their voices [on it] and be themselves.” And that created like, “What would my buddy Taylor Hanson do for this song? What would AJ McLean from Backstreet Boys [do]?” Me and AJ were golfing. I was like, “Yo, what would you do if you were to sing this song?” Then he did his take on it, and that’s what took it to how it ended up, which was basically eight different people doing their take on what they would do on “On The Way Down.”

PEOPLE: How did you get everybody from AJ to Joey, to Drake, to Nash Overstreet on the song?

CABRERA: [It’s] all just people that along the way I have been friends with, and either we’ve always talked about maybe doing something together or never even thought about doing something together, but we’ve always been around [each other]. We’ve done charity shows together or me and AJ golf all the time when we’re in L.A. Me and Drake have done my “Live from Ryan’s Living Room.” 

It’s, for me, just a treat to be like, “Yo, what would you do on this? Would you want to collab?” They’re all like, “Dude, of course.” And some are here in L.A., some are not. I think Drake recorded his vocals in Mexico and obviously Taylor is in Oklahoma, but AJ, Nash and Nick from Walk the Moon came to the studio.

PEOPLE: Who was the most challenging person to secure for the new version?

CABRERA: Getting Joey Fatone to commit and do anything is damn near impossible. He was the last piece of the puzzle, but he was one of the first ones I asked. He’s like, “Yeah, yeah, of course.” When I asked him, he’s like, “Yeah, absolutely, bro, whatever, let’s do it.” Finally, after I got everyone else’s vocals, I’m like, “Joey, the song’s done. Let’s go. I want you to be a part of this.” Because we do so much stuff together. We’re friends first of all, but then also we’ll do private events together. We’ve done corporate events together. We’ve done a lot of things together, but getting him to actually get to the microphone and lay down some vocals, it was a feat all in and of itself.

PEOPLE: Do you have any untold stories about the making of “On The Way Down?”

CABRERA: It was my first time [in New York]. This is the early days when you had to actually go into an office and sing in front of a record label executive and get discovered. They all just were like, “We like the look, we like his voice, but we don’t really hear hit songs.” There was one guy who believed in me, his name was Evan Lamberg, and he was like, “Yo, I’m going to figure this out. I’m going to give you some money so you can live, and I’m going to send you to New York, and you’re going to continue writing until you get it.”

I got together with Curtis Frasca and Sabelle Breer, whom they introduced me to and at the time, they had just got off doing some stuff on Avril Lavigne’s first record, which I was a fan of. We worked together and just locked away and created “On The Way Down.” At the time, we didn’t think that was actually ever a single. We’d written a couple other songs that were like, “That’s a single. Oh my God, this is going to be the biggest hit.” We thought “40 Kinds of Sadness” was going to be huge. Then the label heard them all, and they were like, “Yo, this ‘On The Way Down’ song.” I was like, “We didn’t even know if that would make the record.” Somehow that turned into the song that got me signed. The same labels that turned me down originally, came back and were like, “Yo, this is a hit.” Then, they played it for Johnny Rzeznik, and he was like, “This is it.” I was like, “I guess that’s what we’re going with.”

PEOPLE: You debuted on reality TV back when the format was really first emerging. What was that like for you?

CABRERA: Back then it was totally fine and normal because they just followed us around. It wasn’t, like, production — it was a cameraman, a couple of people behind the thing and us doing our thing. It actually was fun because it was like, “We’re just going to film me all week and whatever you all do is what you all do.” Somehow they pieced together a show that was entertaining enough to do well. For me, it was super fun because anytime you get to be yourself, have fun and then people get to see it, it’s cool. You’re getting a behind the scenes look at who the artist was.

I was like, “I’m creating an album, I’m creating these songs, and you’re going to hear them hopefully, but you don’t know who I am.” Being on a show like that, people got to know you a little bit. Obviously, you don’t give everything away. You still have your own personal stuff that you’re not doing. But at the time, we weren’t hiding anything. You got a glimpse into what life was like. It was before crazy album sales, and you got a little bit too busy to do anything fun like that. It was an early glimpse as to what life was like in Los Angeles in 2003 when me and Ashlee were making our albums. And then obviously Jessica and Nick were doing their thing. We were silly, and we were just always joking around, and I think that helped obviously with album sales because people felt like they got to know you.

PEOPLE: And it was notably before social media.

CABRERA: This was before you got to pick and choose how you were viewed. We forgot that there were cameras there. There was things that were like, “Oh, maybe I probably wouldn’t have presented myself that way, but f— it. It was real.” That, I think, is a good thing. When you can’t even really filter yourself, you’re just unapologetically yourself. That kind of reality show will never be redone the way it was in that time period because everything [is] produced. You know it is now. It’s no secret that after that, everything became, “Let’s just find some random people, put them together because they’re pretty, here’s some storylines for them and when they get boring, let’s feed them some s— to make it exciting. Let’s give them some drama.” It’s just the truth of the matter.

PEOPLE: Is there a celebrity fan that really surprised you over the years?

CABRERA: There’s been a couple. I think the biggest holy s— moment for me was, a while ago, Brad Pitt. I think [Ashlee] was doing the Orange Bowl, maybe. Somehow we ended up backstage with Brad and Jennifer Aniston. I’m a huge Friends fan, and most of my friends probably would’ve been like, “Dude, what was it like meeting Jennifer Aniston? Holy s—.” But for some reason, I was like, “Oh my God, it’s Brad Pitt.” He got something about it that just draws you in. I literally melted. I wasn’t even there anymore.