Over the past 25 years, artists typically associated with country music have tried their hands at the "high, lonesome" sound of bluegrass. Typically, these country stars' regional origins —though bluegrass isn't strictly Southern or Appalachian— and past creative paths informed their decision to bring a fresh perspective to a tradition-grounded yet ever-evolving art form.
Acts returning to their roots after finding wider fame in Nashville range from living legend and folk balladeer-at-heart Dolly Parton to the always unpredictable Sturgill Simpson. Of course, this list doesn't sum up every album from the bluegrass-country interchange, with snubs including critically-acclaimed works by Del McCoury Band collaborator Steve Earle and Ralph Stanley acolyte Jim Lauderdale. Thus, consider the following eight selections as jumping-off points into a fairly recent trend that's introduced the stylistic innovations of Bill Monroe, Earl Scruggs, Lester Flatt, Ralph Stanley and other pillars of bluegrass music to a broader audience.
The Grass is Blue, Dolly Parton (1999)
With 1999's Grammy award-winner The Grass is Blue, Parton began a three-album stay with bluegrass tastemakers Sugar Hill Records. A cover of Billy Joel's banjo-fueled country-rock selection "Travelin' Prayer" sets the tone for Parton's exploration of the Appalachian folk music that'd informed her songwriting all along. This journey continued on Little Sparrow (2001) and Halos & Horns (2002).
Parton's 2014 album Blue Smoke deserves honorable mention for doing an equally effective job at pushing her ever-present roots music influences to the forefront.
Mountain Soul, Patty Loveless (2001)
Bluegrass-country crossover reached its peak to date on the first volume of Patty Loveless' Mountain Soul series. Like others on this list, Loveless didn't limit her source material to the bluegrass canon, though she knocks it out of the park with songs by the Stanley Brothers ("Daniel Prayed") and Reno and Smiley (Travis Tritt duet "I Know You're Married (But I Love You Still)"). Other high points on the album point back to the works of everyone from Parton and Porter Wagoner (Jon Randall duet "Someone That I Used to Know") to Martina McBride ("Cheap Whiskey").
Loveless reconvened the Mountain Soul series in 2009 with a Grammy award-winning sequel.
Up the Ridge, Dierks Bentley (2010)
After teasing a pivot to his folk and bluegrass roots on 2009's Feel That Fire via Patty Griffin ("Beautiful World") and Ronnie McCoury ("Last Call") collaborations, Dierks Bentley went all-in on 2010's Up on the Ridge. Beyond a list of featured guests that ranges from Miranda Lambert to Del McCoury, Bentley assembled a who's-who of studio pickers and singers. On vocal harmonies alone, there's Vince Gill, Sonya Isaacs, Alison Krauss and Chris Stapleton.
More recently, Bentley laid the blueprint for injecting bluegrass elements into modern, radio-friendly country with 2018's The Mountain.
Homecoming: The Bluegrass Album, Joe Diffie (2010)
Long before his emergence as one of '90s country's top traditionalists, Joe Diffie was an Oklahoma grasser in the band Special Edition. For his next-to-last album, Diffie returned to his roots with mandolin maestro Mike Compton and other top-shelf musicians. There's not a single throwaway track on a collection that ends with a reimagining of the Black Crowes-via-Otis Redding stomper "Hard to Handle."
The Bluegrass Album, Alan Jackson (2013)
In 2013, Alan Jackson explored his Southern music roots with a second installment of gospel collection Precious Memories as well as his aptly-titled The Bluegrass Album. The latter's what you'd expect (in the best way) from a set of acoustic, grassed-up Jackson compositions. Gorgeous, harmony-laden covers of The Dillards ("There is a Time"), John Anderson ("Wild and Blue") and Monroe's Blue Grass Boys ("Blue Moon of Kentucky") serve as the cherries on top.
Happy Prisoner (The Bluegrass Sessions), Robert Earl Keen (2015)
One of the finest songwriters to ever emerge from Texas tried his hand at not just bluegrass but also old-time, folk and early country sounds on this double album. Beyond delving into standards penned by Monroe ("Footprints in the Snow"), Carter Stanley ("White Dove") and John Hartford ("Steam Powered Aeroplane"), Keen's survey course on American music teaches listeners about Bristol Sessions alums the Carter Family ("East Virginia Blues") and Jimmie Rodgers ("T is For Texas," featuring Lyle Lovett) .
Swimmin' Pools, Movie Stars..., Dwight Yoakam (2016)
West Coast country game-changer Dwight Yoakam's high tenor range suits grassed-up revisions of some of his best-loved songs plus an album-closing cover of "Purple Rain." The latter elevates the soul and sorrow in the original without sounding the least bit ironic.
Also note that Yoakam titled his album Swimmin' Pools, Movie Stars... as a hat-tip to Flatt & Scruggs: a formative bluegrass duo popularized by the Beverly Hillbillies opening theme.
Cuttin' Grass Vols. 1 and 2, Sturgill Simpson (2020)
Naturally, Kentucky native and genre chameleon Simpson pulled off the country-to-bluegrass transition as effectively as anyone on this list (sans Loveless) when he altered his outsider country compositions to suit this two-volume pandemic project. To make the most of his latest musical evolution, Simpson recruited elite talent for a makeshift bluegrass band: guitarists Tim O'Brien and Mark Howard, banjoist Scott Vestal, fiddler Stuart Duncan and mandolinist and backing vocalist Sierra Hull.
