In May 2022, Gavin DeGraw stood on a precipice: He had just released his seventh studio album, Face the River, and completed his contract with Sony Music.

The GRAMMY-nominated singer/songwriter had free reign for his next career move. And with the 20th anniversary of his seminal debut, 2003's Chariot, on the horizon, DeGraw had an idea.**

"I've been living with these songs, and I've been fortunate enough to have success with these songs already in the past," he tells GRAMMY.com, "[so I thought], What a great opportunity to recut the songs.

Chariot 20 features re-imaginings of all 11 songs on the original album, as well as two unreleased tracks from the Chariot sessions: "Get Lost" and "Love Is Stronger (Alright)." Bringing new life to the music, Chariot 20 features lush instrumentation and playful riffs on each tune, resulting in a version of the album that's even more true to who DeGraw is as a performer.

"I've been playing these songs for so long, and I feel like the performances had actually improved, and the level of execution had escalated," DeGraw says of Chariot. "Why not take the opportunity to document that, and enjoy that, and make it sound even that much more intimate and special?"

In celebration of Chariot 20, the upstate New York native Zoomed with GRAMMY.com from a park in New York City to reflect on the impact Chariot had on his career — from allowing him to pay off student loans, to putting him on stage with his idols.

Re-recording albums has become somewhat of a trend as of late, whether it's to regain ownership or to celebrate an anniversary. Was your re-recording of Chariot simply inspired by its 20th anniversary? Or was it something more for you?

All of the above. The fact that the 20th anniversary of the record was coming up right after I had just satisfied my record deal obligations with Sony New York City, it was all great timing. Trust the universe, right? 

It was just right to make this record the way we made it, and with the partners that we made it with. You know, I had just made a record just a couple years earlier, with Dave Cobb, and we had cut a record called Face The River. And I love the way the record sounded.

That was my first time working with Dave, and I thought he did such a great job. The sounds and the performances were just so authentic and so homegrown. He really captured my voice in the most authentic way. I realized that he'd be the perfect guy to recapture the Chariot record.

This recording brings new life to this album, and also a level of authenticity that I really believe in for this album. These intimate songs, luckily, had become a lot of hit songs for me, but [Dave] was able to capture these songs in an even more intimate way. It really feels just so from my mouth to your ear.

Also, it was a fun excuse to put these other new songs on that were written from that same era that didn't make the first record. One of the things that I'm excited about is the way that [my new label] Sony Music Nashville has gravitated towards those other songs from that era. Not only "I Don't Want to Be" and "Chariot," but other songs from that era that I'm proud of.

Did you have a favorite song on Chariot before you re-recorded the album? And if so, did that change once you revisited all the songs again?

Well, I'll tell you that the two that didn't quite make the first record are the two real surprises for me. But also the ones that did make the first record that surprised me probably would be "Meaning" and "Overrated." Because the recordings are so simple, and the songs really just speak. There's no tricks, it's just very simple, very authentic, very pure.

Before you actually announced the full album, you released the re-recorded version of "Chariot." In a post about it, you said, "I've changed so much, and I wanted my music to reflect this growth." What are the biggest ways you feel you've changed since releasing Chariot, whether as an artist or even a person, or maybe a little of both?

I think the main thing would be the level of confidence in your performance as an artist. There's 20 years of growth of development of your skill set and of your confidence level. And, you know, 20 years ago, you're evolving, figuring out, Who am I? What kind of record do I want to make? [Today], your voice is more lived in, more mature. [You're] just better at your craft due to your life experience.

There's just a level of living in the song now. You can hear it in the delivery: everybody is so deliberate in what they're doing, performance-wise. And all that comes from that believability.

You've talked about how you had several frustrating years where nothing was really happening for you before Chariot came along. And you were in your mid-twenties when you released it, which can be seen as "old" in this industry. When you finished Chariot, what do you remember thinking about what it could potentially do for you as an artist?

When I was putting that first record out — and even before I put that first record out — I was putting so much pressure on myself, as many people put pressure on themselves, to make a good living. Getting a record deal and making a record was a byproduct of endless hours of pursuit, and sweat, and frustration. Basically, getting my ass handed to me in real life trying to make $1 here and there playing live gigs at bars and clubs. 

My motivation was, I'm broke, I want to make a living doing this. So your motivation at the very, very beginning is much simpler, right? And then, when you're not broke anymore, your motivation graduates a little bit. Now, [it's] how do I continue to grow artistically, and make a living, and express myself? How do I demonstrate that I'm improving at my craft? 

I'll never forget being broke. I can't shake that feeling, and that chip on my shoulder that I had as a kid never went away. It keeps me working hard. It's motivation for me. It reminds me how lucky I am to have an opportunity. It reminds me that I'm representing where I'm from. I'm representing the people I grew up with who had the same frustrations, had the same stories. And so you're not just making music for yourself, you're making music for a culture of people.

What was the reaction like when you first released the album, and when did you kind of start to feel the shift?

Personally, I wanted "I Don't Want to Be" to be the first single and "Chariot" to be the second single, but we went with "Follow Through." When "Follow Through" wasn't getting the love we wanted to get early on, that's when I got a phone call about "I Don't Want to Be" having an opportunity to get placed on TV, which was obviously a huge, huge gift to me. 

Once that song got picked up for ["One Tree Hill"], the focus switched to support the success of "I Don't Want to Be," and it fortunately proved worthwhile. We probably worked that song for a full year or so before it was a hit, and that was obviously life-changing.

I hope you had an "I told you so" moment about "I Don't Want to Be" being the right first single.

No, no, I would never do that. Because here's the way I view it. As an artist, if you're lucky enough to end up with a great partner at a record company; anything that they're embracing of yours, you're lucky they're embracing it at all. If someone at the record company chooses one song as the better choice above what you wanted, don't blame them, here's why — you're the one who recorded that song! You handed the album to them! That's on you! [Laughs.] 

That's a lesson to you as the artist of, S—, maybe I need to do a better job next time if I don't believe that any one of these things could be the one. That's my problem.

Many people probably associate "I Don't Want to Be" as the "One Tree Hill" theme song. But what do you associate with that song? Is there a special memory or moment that stands out?

The main thing that I think about for that song is, that is my autobiography. I didn't write it for anything other than my real life. It was one of the songs on my album, and it happened to be the song that a show picked up, and thank God they did. But I still think about the roots of the song when I think about that song.

To add to that, that's the song that paid off my college loans. So, I'll take it!

Do you remember the moment or the time that you realized that this album had actually changed your life?

The phone call was big regarding placement, but I don't remember the exact moment where I thought, Okay, cool, I made it. Because it didn't seem to happen like that for me. I will say, the skeptic in me was worried about when the magic carpet was gonna get pulled out from under me at every moment.

Probably the biggest thing for me was getting a phone call to do the first Billy Joel show [in 2014]. Seeing him live when I was 15 years old was the deciding factor for me to become a musician for living, so when the call came in to open for Billy, that was maybe the moment I thought, Wow, my hero has invited me to play a show. This is a big deal for me

Does he know that he's your childhood hero? Did you get a chance to tell him that he's the reason that you got into music?

I think he may know that by now. I hope he does. Doing those shows with him, opening for him, those were huge, huge validation moments for me, as a musician, as a fan, as a native New Yorker. It's like opening up for the Pope at the Vatican, playing with Billy in New York.

What are some of the most unbelievable opportunities you remember getting because of Chariot?

One of the biggest ones would probably be the Songwriters Hall of Fame event [in 2003]. I got a phone call from Phil Ramone, who's a very big producer, a legendary guy. He asked me what I'd like to do during that show and gave me a couple options. My part was performing a Phil Collins song, "Against All Odds," doing a speech, and then giving Phil Collins his award. 

What an honor to be part of that. He was a lovely guy. When I walked off stage, the first person that stopped me to congratulate me on my little part of the show was Brian May from Queen. And I'm a huge Queen fan. He said something very regal as a compliment, "That was magnificent" or something that I didn't deserve, which was lovely. It made me feel good.

That night, there were so many amazing artists performing. Here's who played that night — and this is why it means so much to me. That very night, it was the first time I'd seen Billy Joel in person. He was running to the stage to go do a song in honor of another songwriter named Jimmy Webb. So he played that night. Barry Manilow played that night. Van Morrison played that night, and the guy playing piano, singing harmonies for Van Morrison, was Ray Charles. Alicia Keys played that night. Tony Bennett played that night!

I was so beside myself that I was invited to be part of this very special musical community that, at the time, and even now, I feel like, I don't deserve that. I was just so honored to be invited to be part of that, musically, artistically. What a moment for some dude in some small prison town in upstate New York who grew up playing barrooms. 

To be invited to be part of that, I was pinching myself. I'll never ever forget a moment like that. A very extraordinary evening for a guy like me.

And Chariot did that for you!

Chariot did that for me. Isn't that unbelievable? Honestly, I'm still baffled by it.