Alison Krauss Talks 'Windy City,' Reveals Which Artist Her Son Warned Her Not to Cover

Randee St. Nicholas
Alison Krauss

In modern pop, the decision to perform roots music of any stripe is not to be made lightly. It connotes turning your back on progress and spitting in the eye of newfangled technology. From a commercial standpoint, playing bluegrass or western swing or Dixieland jazz almost guarantees that a musician will spend his or her life on the fringes, touring heavily to reach small pockets of listeners that still like their tradition uncut. 

Unless, of course, that musician is Alison Krauss, who has blown through these constraints like a runaway train. Despite being associated primarily with bluegrass, she's released five gold-certified albums as a soloist and with her band Union Station; a live recording with Union Station and a compilation of the group's early work both went double platinum. 

And any supposed barriers between Nashville's constantly evolving mainstream and the more insular, tradition-first side of the genre seem to evaporate when Krauss appears. She produced the Nashville stalwart Alan Jackson's great 2005 album Like Red On a Rose; she hit No. 3 on the Country Airplay chart as Brad Paisley's counterpart on "Whiskey Lullaby;" she sang with Taylor Swift on a standout rendition of "Red" at the CMAs in 2014. In Krauss' hands, tradition is not the fusty province of record collectors but an adaptable, durable source of popular music.

So it makes sense that on her new record, Windy City, renditions of movie music sit next to covers of bluegrass B-sides, while esoteric Willie Nelson records are at home with Glenn Campbell standards. Krauss found a suitable partner in producer Buddy Cannon, whose resume extends into nearly every nook and cranny of the last four decades of country music. The two had worked together for years -- "I don't even know if I was 20 yet [when we first started]," Krauss tells Billboard -- but always with Krauss singing harmonies or backup on another artist's recording session. She had never laid down a lead with Cannon behind the boards.

Despite the mammoth nature of Krauss' accomplishments, she was nervous to solicit Cannon's help. "I was bashful," she admits. "What if he's like, 'No way, I hate you! I hate you so much!' I sat and stewed on it for a while; it kept bothering me. I finally got the nerve up." It's hard to imagine any producer turning down a chance to work with a 27-time Grammy winner; sure enough, Cannon agreed to participate. 

With that hurdle cleared and a producer in the bag, Krauss and Cannon set about picking songs for her to interpret. "I'm not a songwriter," Krauss says. "I can arrange things, and I can edit, but I'm not a poet." Traditionally her albums pull from the bluegrass repertoire or from the work of marvelous songwriters who laid down their best work before Krauss' 1985 debut album -- Lennon and McCartney or Allen Toussaint or Townes Van Zandt. She pooled her lifetime of listening with Cannon, and the two compiled a list of tracks to record. Dear to Krauss: The Osborne Brothers' "Windy City," Vern Gosdin's "Dream of Me." Dear to Cannon: Glenn Campbell's "Gentle On My Mind," Roger Miller's "River City." 

Two of the songs on Windy City were popularized by Brenda Lee, a '60s spark plug who scored hit after hit after hit during that decade; Krauss was compelled to record these tunes even though she was advised to stay away from them. "My son and I would drive around and listen to these songs before we cut 'em," she recalls. "He would go, 'oh mom, you oughta not do Brenda's songs. You're not gonna be able to touch that. She's killing it.' But I love her so much," she continues cheerfully. "I did it anyway." 

Many of the tunes that Krauss picked have already been reinterpreted multiple times, ping-ponging their way through history. Krauss originally heard "Dream of Me" performed live by the duo Jim & Jesse. "I wanted to cut that on my first album," she says. "Ken Irwin from Rounder Records said, 'you can't cut that, that's a hit for Vern Gosdin.' I didn't even know it, 'cause all I was listening to was bluegrass at the time."

"Dream of Me" is not the only piece of reused material here -- though "Gentle On My Mind" was a hit for Glenn Campbell, it was originally recorded by John Hartford; Aretha Franklin and Dean Martin also recorded versions of the track that found chart success in the U.S. and U.K., respectively. "You Don't Know Me," co-written and first recorded by Eddy Arnold, would later enjoy fame in the hands of Ray Charles, Elvis Presley, and Mickey Gilley.

So Krauss is part of the most venerable tradition in pop music: recycling. But the range of the source material for Windy City and Cannon's extensive studio experience afforded the singer several new opportunities during the recording process. You don't usually hear her with a buffeting brass section like the one that appears on "It's Goodbye and So Long to You." "I said to Buddy, we've gotta get a tuba!" Krauss remembers. "It'd be so great. When I was growing up, Merle [Haggard] took horns on the road. That was real common, to hear horns in country." 

She also found herself singing outside of her rhythmic comfort zone -- Krauss' adaptation of Willie Nelson's "I Never Cared For You" proceeds in a manner she describes as "bossa nova-like" -- and playing with a swooning orchestra. The presence of pedal steel guitar beneath Krauss' voice is unusual in her discography as well.

"It was like seeing something for the first time," she says of Windy City. "I never did anything like this." For Krauss, tradition remains a source of rejuvenation.