In the late hours of a June 2001 evening, a performance by a young, fresh-faced band was broadcast for a national audience on Jay Leno’s Tonight Show. Late-night talk shows draw in musical artists of all stripes, but at that time, in the era of boy-band pop and a nascent rock revival, a group like Nickel Creek, consisting of three teens and twentysomethings sporting bluegrass instruments, were not the kind of act one would expect to see on a marquee network program like Leno’s.

Yet the trio of Sean Watkins (guitar and vocals), Sara Watkins (fiddle and vocals), and Chris Thile (mandolin and vocals) had undoubtedly arrived. Leno’s would be just the first of many national stages for the upstart band from Southern California. The front half of the aughts resulted in a host of achievements and accolades for Nickel Creek, including Platinum certification for their self-titled debut and a Grammy for Best Contemporary Folk Album bestowed upon their 2002 sophomore outing This Side, which went Gold.

That five-year stretch culminated in the 2005 masterpiece Why Should the Fire Die?, which joins Nickel Creek and This Side in a vinyl reissue package by Craft Recordings, released in the first weeks of November. Timed for the 20th anniversary of the debut LP, the vinyl reissues provide listeners a chance to re-examine the albums that made Nickel Creek a household name. Technically, the trio had two records prior to their Sugar Hill debut: Little Cowpoke and Here to There, released in the 1990s when the Watkins siblings and Thile were still youngsters touring regional folk music circuits. But Nickel Creek, produced by bluegrass maven Alison Krauss, is the group’s proper debut, its formal announcement to the world — a far cry from the days when Little Cowpoke was being released on Choo Choo Records.

Talking to Watkins over the phone just as the vinyl editions were being made available to the public, I ask her what about that moment at the start of the new millennium allowed Nickel Creek to sell a million records. For her, Nickel Creek “were very much in the right place at the right time” owing to two factors: their star producer and a film soundtrack that surprisingly swept the nation.

“A lot of it had to do with Alison Krauss producing the record, and with O Brother, Where Art Thou? coming out that year,” she says. “There were several major articles about the soundtrack to O Brother, Where Art Thou?; that record really took the folk world by storm, and it also got a lot of listening from those who didn’t usually seek out folk and traditional music. We were lucky to be included in that conversation. We got mentioned in a New York Times article about the soundtrack, even though we weren’t actually on it. We were really blown away by that. Somehow, we got caught up in a storm and reaped a lot of benefits from it.”

Nickel Creek contains songs that many would identify as classics of the band, such as the forlorn ballad “The Lighthouse’s Tale” and a jaunty rendition of the folk standard “The Fox”. But in interviews over the years (particularly for the 2014 reunion album A Dotted Line, recorded after a seven-year hiatus), the band have articulated a common disjunction between a fan’s experience of an artist’s music and an artist’s relationship to their music.

It is easy to forget, given the musicians’ prodigious talent, that Nickel Creek and This Side were made by musicians in their late teens and early 20s. Where a diehard fan may love a Nickel Creek album track, to the band members themselves, those tunes can serve as reminders of their earlier, more “awkward” selves, to use a word of Watkins’. In an interview given around the time of A Dotted Line‘s release, Thile described going back to some of the band’s early songs as akin to looking at high school yearbook photos of himself. “It’s impossible for me to separate how I felt in my body and my soul at the time from the music itself,” Watkins explains. “Those things are completely united in this band, and in most situations, I’ve been in.”

Have these new vinyl editions given Watkins a chance to look back on these records and discover new things? “I definitely listen to the music with a lot more compassion than I used to, say ten years ago. The more time goes by, the more grace I have for what we were trying to do in our earnestness,” she says. “We were trying really hard to do the best we could, to make the best records we could. Thank goodness that people develop and change! The distance has afforded compassion and the ability to see more than just the embarrassing things. I can hear the good moments now and think to myself, ‘Oh, that was pretty good… for kids.'”

Sean, Sara, and Chris may have been “kids” back in 2000 — Sara and Chris were 18, Sean 22 — but as Watkins describes it, they supported each other well as the spotlight of public attention fell upon them. It helped that Nickel Creek’s largest audiences came from the Americana and folk scenes. She recalls, “I don’t think any of it was terribly overwhelming. [The fame] was still on the folk music level; we weren’t pop stars. When you’re 18, 19, you adapt to things pretty quickly, especially when you have a group of people who were along for a ride. If it were just me as a solo artist, I think I’d have been more shocked by it all, but I was able to ride the wave with my bandmates. When you’re in a healthy band, you have your own little world, which made it easier to adjust to the changes happening around us.”

Nickel Creek followed up their lightning-in-a-bottle debut with This Side. This more eclectic and experimental affair featured fewer traditional folk tunes and more off-kilter arrangements and cover choices, including Pavement’s “Spit on a Stranger”. Watkins lists an interest for that album in “exploring percussion elements that didn’t involve drumsets. You’ll hear a lot of tapping on instruments.” The booming bass arrangement on the chorus of “Green and Gray” and the gentle yet tense instrument hits on “I Should’ve Known Better” exemplify the trio’s percussive explorations.

Yet while This Side gave the group their first Grammy win, they regard it not as an apex but rather a liminal time for their career. “We’ve all described that record as fairly adolescent. There are some cool moments on it, but it feels transitional to me, which is where the feeling of adolescence comes from.”

Watkins points to the example of the deep cut “Sabra Girl”, a song written by the Irish musician Andy Irvine, originally released as “Time Will Cure Me” by his band Planxty. She identifies a “mortifying moment” in the track that’s indicative of this adolescent phase. “I was really shy talking about anything that had to do with relationships, anything that sounded remotely sexy. There’s a lyric in ‘Sabra Girl’ that goes, ‘Deep was the talk as we lay on your bed.’ I felt uncomfortable singing that lyric in my 17-year-old, shy self, and so we changed it to, ‘Deep was the talk, forever my debt.’ I regret that so much now. Irvine — who is a world-class musician, someone I greatly respect — called me out five years after the record was made, and I was very apologetic.” (On the 2014 Dotted Line tour, Watkins sang the line as originally written.)

This Side may conjure up memories of youth’s awkwardness for Nickel Creek, but Watkins recognizes, in keeping with the gentle eye with which she now looks on the group’s early music, “There are moments of cringe, but I try to be kind to myself about it. What’s done is done.”

When Nickel Creek put out its first two records with Sugar Hill, they treated the future as an open-ended proposition. The band committed to lengthy tours, with few breaks in between each tour and record recording session. “We were very in-the-moment. At some point, a manager was like, ‘What’s your five-year plan? Your ten-year plan?’ And our answer was, ‘Uh, keep touring?'” Watkins says, laughing. “We didn’t have a master plan. Thank goodness there were others around us who could help us develop our touring into bigger and bigger rooms, and with some of the business stuff.” In-the-moment as the band was, there is a clear arc of musical development evident in Nickel Creek’s progression to Why Should the Fire Die? No gap in the trio’s discography is more distinct than the one between This Side and Fire.

A melancholy record, full of songs about longing and loves lost, Why Should the Fire Die? took the band from its “adolescent” period into the rocky emotional terrain of adulthood. It also features some of Nickel Creek’s finest songwriting, such as the tender ballad about lost faith, “Doubting Thomas”, and the controlled rock ‘n’ roll build of “Helena”. The music was timely, too. The Sean-penned breakup song “Somebody More Like You” gels with mid-2000s emo, particularly its send-off line, “I hope you meet someone your height / So you can see eye to eye / With someone as small as you.” These were no longer the eager, fleet-of-finger musicians gallivanting through sunny bluegrass instrumentals. These were grown-ups.

Watkins reflects on Fire with fondness. “I really enjoyed where we ended up landing on Why Should the Fire Die?, especially because that transition felt like a long time for us. We tried to make a record before we made Fire; we had some material we liked, but we were working with someone who kept telling us to write a bunch more songs. It kind of made us mad, but it ended up being the best feedback possible because we started writing more together, and we felt like we needed to prove ourselves in a way that we hadn’t in a while by that point. And we ended up with Fire, which is a record we’re all still quite proud of. It just took us a while to grow up into it.”

The album’s subject material’s often bleak quality signifies a clear departure from Nickel Creek and This Side. This sonic evolution was built from the ground up; the making of the music itself informs the weightier themes. Krauss no longer sat in the producer’s chair, and new collaborators helped further push Nickel Creek’s music into what has often been dubbed “progressive bluegrass” territory.

“It’s not sparkly bright,” Watkins says of the production, “and our first two records were very much so. We were working with a great engineer named Gary Paczosa, who gets beautiful tones that are shiny and sparkly; he really revolutionized how bluegrass is captured in the studio. On Fire, we were going for something different, and so we worked with a producer named Eric Valentine, who was also the engineer. The darkness we achieved on that record is a pleasing contrast sonically, especially for a band that doesn’t have a lot of low end coming from keyboards, organs, or a kick drum, just an acoustic bass.” The band does incorporate a drum set during the climax of “Helena”, and would further utilize this kind of percussion on its cover of Mother Mother’s “Hayloft” on A Dotted Line.

With Fire, the trio showcases just how far their musical development had come. Through their eclectic musical personalities, they took the skills developed on the small bluegrass festival stages of their youth and brought them to bear on the adventurous songwriting of their adulthood. As the music got bigger, its reach did as well. On their “Farewell (For Now)” tour in 2007, whose conclusion marked the beginning of the band’s hiatus, Nickel Creek played Coachella and toured with Fiona Apple. The latter would go on to collaborate with Sean and Sara for their Watkins Family Hour project. Watkins recounts that many of their fans grew alongside them; for instance, many of the trio’s young fans showed up to that tour, having been too young to attend the shows earlier in the decade.

In its reflection of Sean, Sara, and Chris’ growth as musicians, Why Should the Fire Die? bookends Nickel Creek’s most productive period. The three albums in this vinyl reissue can each be thought of as an expression of individual seasons of life: Nickel Creek, the wide-eyed sincerity of youth; This Side, the verve and confusion of adolescence; and Fire, the sorrows and struggles that come from making one’s way through the world as an adult for the first time.

As Watkins puts it, Fire‘s turn to the dark was entirely natural and could not have happened any other way. On their first few LPs, she and her bandmates “were these optimistic 17- and 19-year olds, who hadn’t gotten their hearts broken, and still had a very idealistic perspective that hadn’t been challenged. We just hadn’t lived that long. It was imbalanced in many ways that were pleasant for people in a lot of ways but were honest for us. The emotions in the first two records would not have been honest had we just repeated them in Fire.”

Although Sean, Sara, and Chris remain best known for Nickel Creek, their musical worlds blossomed in a way that would have been hard to imagine back during their humble performance on Leno. The list of projects seems to grow exponentially: Chris has the Punch Brothers and collaborations with the likes of Edgar Meyer, Brad Mehldau, and Yo-Yo Ma; Sara has, in addition to several solo LPs, a role in the acoustic music supergroup I’m With Her (with Aoife O’Donovan and Sarah Jarosz); Sean formed a duo with Switchfoot’s Jon Foreman called Fiction Family, in addition to numerous solo outings of his own.

Nickel Creek, This Side, and Fire form a multifaceted musical journey, yet looking back now, even in the warm light of nostalgia, they represent a starting point for three remarkable music careers. I ask Watkins if the rapid success of Nickel Creek after the self-titled album resulted in expectations that their songwriting continue in that style, and her answer evinces a confidence that one can hear developing in the progression from Nickel Creek to Fire.