Ricky Skaggs had enjoyed even more country hits and awards than Carpenter, but his streak of hits ran dry too. He realized that the music he was most comfortable with in his 40s was bluegrass, and he released his return to the genre, 1997’s Bluegrass Rules,on Rounder. Part of his new mission was to pay tribute to the giants of the bluegrass’s first generation, whether it was an album tribute to Bill Monroe or a PBS television special that captured Skaggs, Earl Scruggs, and Doc Watson in concert together, backed by such admirers as Krauss and Darrin Vincent. Rounder released the audio CD from the PBS telecast, highlighted by the reprise of Flatt & Scruggs’ signature song, “Roll in My Sweet Baby’s Arms.” “Three groups really shaped this music,” Skaggs claimed, “Bill Monroe, the Stanley Brothers, and Flatt & Scruggs. It’s important for me to pay honor to them while they were still around, because one of these days they won’t be.”

Spurred on by Hazel Dickens’ early example and by Krauss’s unparalleled success, women started finding a place in the previously all-male domain of bluegrass, and many of them recorded for Rounder: Claire Lynch, Lynn Morris, the Stevens Sisters, Alecia Nugent, and Rhonda Vincent. Vincent, who had also taken a fling at commercial country, thrived upon her return to bluegrass; she won the IBMA’s Female Vocalist of the Year Award seven times in a row, and you can hear why on “Lonesome Wind Blues.” Darrin Vincent, her kid brother, sang harmony on the track as he had on so many tracks as a member of Ricky Skaggs & Kentucky Thunder. In 2007, though, he formed a duo act with Jamie Dailey, the longtime lead singer for Doyle Lawson & Quicksilver. “Jamie had become the sound of Quicksilver,” Irwin points out, “and Darrin was known for singing parts behind Ricky. It was a funny situation; they had to establish a new sound other than the one they were known for.They soon found they had a similar kind of phrasing, similar senses of humor and similar tastes, so the brother-duet approach made sense. They were so well known and so well liked in the bluegrass world that they got a standing ovation at IBMA before they played their first note of their first gig. They hit that stage and it was as powerful as the Johnson Mountain Boys.” Songs such as “More Than a Name on the Wall” from their 2008 debut album Dailey & Vincent helped the duo win the bluegrass world’s top prize, IBMA Entertainer of the Year, in their first two tries, 2008 and 2009.

The two previous years, that prize had been won by the Grascals, another new band. They too grabbed the attention of the bluegrass world with a poignant story song, Harley Allen’s “Me and John and Paul,” which wasn’t George Harrison’s autobiography but rather the tale of three high school friends. “When we recorded Bela Fleck with Spectrum, the fiddler was a kid named Jimmy Mattingly,” Irwin explains. “Many years later he called me up to say he was playing bluegrass again after years on the road with Dolly and Garth. They had a lot of energy and were willing to improvise a lot. And Terry Eldredge is just one of the best singers in bluegrass and would probably be one of the best singers in country if anyone was interested in real country these days.” One of the decade’s other top bluegrass bands was Blue Highway, which boasted three accomplished singer-songwriters in Tim Stafford, Shawn Lane, and Wayne Taylor and an 11-time IBMA Dobroist of the Year winner in Rob Ickes (who also has four solo albums on Rounder). Their ability to balance such songcraft and virtuoso picking can be heard on Stafford’s “Through the Window of a Train.”

Rounder made only a few stabs at the jazz market, and the two efforts that clicked had obvious connections with the kind of roots music the label had always done. When Bela Fleck returned to the label, for example, his roots in bluegrass made it easy for the Rounder audience to grasp his jazz and world-music recordings. And when Madeleine Peyroux recast country-folk influences in the jazz-vocal tradition, that same audience could make the connection to Norah Jones’s albums. Little did those listeners know that Peyroux had been doing this before Jones had ever released a record. “I heard Madeleine’s first record on Atlantic in a boutique shop,” Rounder founder Marian Leighton Levy remembers, “and I instantly said, ‘Who’s that? That’s an incredible voice.’ I was disappointed and puzzled when she completely dropped out of sight after such a promising start. Years later I heard that she was playing again in New York and looking for the right kind of record deal. I knew we were the label, so I pursued her. Like a lot of people, I refer to her as ‘the first Norah Jones.’” Peyroux’s first solo album in eight years was 2004’s Careless Love, produced by Joni Mitchell’s producer and ex-husband Larry Klein. “Don’t Wait Too Long,” co-written by Peyroux, Klein, and Jones’s frequent collaborator Jesse Harris, illustrates the singer’s roots in both jazz and Americana.

Americana was the term invented to market the alternative-country movement and its related branches. One of the movement’s pioneers had been the Illinois band Uncle Tupelo and when the group split, one singer-songwriter, Jeff Tweedy, formed Wilco and the other, Jay Farrar, formed Son Volt. After four albums for Warner Bros. and three for Sony, Son Volt released 2009’s American Central Dust on Rounder. The song “Down to the Wire” had the mesmerizing, dust-storm-across-the-plains drone that marks all of Farrar’s work. San Diego’s Delta Spirit put an R&B spin on the Americana sound in songs such as “Trashcan.” “What I love about them,” says Bill Nowlin, “is they sound like a real band. They don’t disappoint me in person in the way some bands do.”

John Virant not only stabilized Rounder’s business affairs when he became president/CEO in 1997, he also steered the label northward. He was from St. Louis not Canada, but he fell in love with the Canadian prog-rock band Rush while he was an undergrad at NYU and that enthusiasm eventually extended to other north-of-the-border acts. He lured the Cowboy Junkies to the label in 2001 after they had run their course with Geffen. Typical of their sound is “Small Swift Birds” with Margo Timmins’ warbling soprano delivering her brother Michael’s melody and lyrics. Rush, also from Toronto, climbed aboard in 2003, and the band nodded to the label’s string-band roots by releasing live, acoustic-guitar versions of songs such as 1996’s “Resist.” Ottawa’s Kathleen Edwards also signed in 2003, applying an Americana sound to such Canadian subjects as hockey skates, border crossings, bison herds, and small-town shopping malls. But she was also capable of wielding a knotty stick and a tasty carrot to lure an ex-lover “Back to Me.” Sarah Harmer, also from Ontario, joined Rounder in 2004, bringing such sharply observed folk-rock numbers as “Basement Apt.” Harmer sang harmony for such Canadian folk-rock acts as Bruce Cockburn, Blue Rodeo, and Great Big Sea, who all recorded for Rounder as well.

Rounder also crossed the Atlantic to record such British folk-rock acts as Pentangle and Fairport Convention, the latter co-founded by Richard Thompson. He had gone on to make a series of brilliant duo records with his first wife, Linda Thompson, who more or less dropped out of sight after the couple’s 1984 divorce. But Linda made a remarkable comeback with two albums for Rounder, 2002’s Fashionably Late and 2007’s Versatile Heart, reminding everyone how crucial her siren voice and female sensibility had been to those duo records. Richard lent some guitar to the first disc; their son Teddy was prominent on both, and the second album’s title track featured some of New York’s best jazz horn players.

As indie-rock became big business, the emphasis on hipster cool made tongue-in-cheek humor as out-of-fashion as banjos and accordions. Thus alt-rock bands like Ween and They Might Be Giants, who relied on wit as much as electric guitars, were forced onto roots-music labels like Rounder. Ween was free to release a song like “Your Party,” which sounded like a Rush song but was actually a Kinks-like comedy of manners. They Might Be Giants was free to release a song like “Fibber Island,” a fantasia about a utopian isle containing rubber guitars, blueberry-pie houses, and button-up cars with square wheels. The happy, sing-along tune worked as either adult surrealism or childhood fairy-tale, and They Might Be Giants were able to maintain parallel careers as performers for both adults and children. Thus they joined a long tradition at Rounder of children’s performers such as Cathy Fink & Marcy Marxer, Raffi, DinoRock, and John McCutcheon.

Rounder had gotten its start in the polka world by recording Brave Combo and Flaco Jimenez in the ‘80s. But the label moved into the polka mainstream when it signed Jimmy Sturr, who went on to win 17 Grammy Awards for Best Polka Album, most of them for Rounder releases. On two albums, 2004’s Rock ‘n Polka and 2005’s Shake, Rattle and Polka, Sturr adapted rock’n'roll oldies to polka arrangements, often with the help of the original rock stars, as on his collaboration with Duane Eddy on “Rebel Rouser.” With an artist as prolific as Jimmy Sturr, it’s a challenge to find strong material and concepts which he hasn’t already used, but which will show off the strengths and versatility of his band, and Ken Irwin encouraged Sturr to take old rock’n'roll songs and turn them into polkas.”

Willie Nelson got his start in music by playing in Texas polka bands, and “The Beer Barrel Polka” has remained a staple of his live sets. Nelson is one of the few musicians to have recorded more albums than Sturr, so he too needed an angle to distinguish his first Rounder release. This time the concept was to have Nelson revisit the country songs from his youth with T-Bone Burnett producing. This album of hard-core hillbilly numbers is called Country Music, and it’s a fitting irony that in 2010 Nelson had to go outside Nashville to get it released. The one original on the disc is Nelson’s 1959 single, “Man with the Blues,” which is updated with help from Buddy Miller, Jim Lauderdale, Ronnie McCoury, and members of the Nashville Bluegrass Band.

“Who would have expected Willie Nelson and Robert Plant to end up on Rounder?” Scott Billington asks. “As odd as the evolution might seem, though, it makes sense, for their roots are in the same place where we started. It makes sense that we’ll be releasing new solo albums by Gregg Allman and Robert Plant. The crisis of the record business-the plummeting sales, the file sharing, the increased competition for the listener’s attention-has affected Rounder but not as much as the major labels, because we have an underlying aesthetic that they lack. We may deviate from it occasionally, but most of our discs hew to it. It’s not a top-down music where corporations decide what everyone else should hear. It’s an expression that comes from the bottom up; it starts out as music that people make for each other and then it spreads further.”

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