Daniel’s Digs: 7 Best Dolly Parton Bluegrass Deep Cuts

“If I Had Wings” – Blue Smoke (2014)

Dolly’s Blue Smoke release is criminally underrated. Not a straight ‘grass album, but very bluegrass-influenced, “If I Had Wings” is my favorite track on the project. An aching song that would have felt at home on her more well-known Little Sparrow or The Grass Is Blue, this mournful ballad is hauntingly beautiful, and still holds a tinge of the hope that Dolly spread into the world: One cannot predict the future. One cannot undo the past. But we can make the present useful, build a future that will last.

“Endless Stream of Tears” – The Grass Is Blue (1999)

I like to say that Dolly’s bluegrass records really “primed the pump” for the O Brother phenomenon that would be just around the corner. The first in her bluegrass trilogy is The Grass Is Blue, now revered as a classic album in her extensive catalog. Every song on the LP is pure gold, but her originals on here are often overshadowed by the inventive covers. “Endless Stream of Tears” is down-the-middle Dolly bluegrass, complete with soaring vocal runs from Dolly and sweet sibling harmonies from Rhonda & Darrin Vincent.

“Bluer Pastures” – Little Sparrow (2001)

One of the singles from Little Sparrow that some brilliant country disc jockeys decided not to play (can you sense the sarcasm?), “Bluer Pastures” feels like a sequel to Dolly’s song, “The Grass Is Blue”. A spin on the adage “heading for greener pastures”, it tells the story of a prodigal lover returning to her home in the Bluegrass State. It even includes a Monroe reference at the end!

“These Old Bones” – Halos & Horns (2002)

With all of her glitz and glamour, Dolly’s sincere love for the culture of her Great Smoky Mountains always gets me in the feels. This tall tale leans into the mysticism of mountain folklore, telling of a fictional clairvoyant that lived way back in the hills, although the concept is loosely based off a relative of hers. (“That kind of gift runs in our family,” said Dolly.) Her animated voice when portraying the “seer” is filled with charm and affection for her people, and the story itself has a twist at the end. Parton chose this as one of her songs to be adapted for the silver screen in her 2019 Netflix anthology, Heartstrings.

“Blue Valley Songbird” – Hungry Again (1998)

Even before her acclaimed bluegrass trilogy, Dolly’s appreciation for the genre still seeped into her music. Hungry Again features the heartwrenching tale of the “Blue Valley Songbird,” inspired by an actual Blue Valley near Chattanooga, TN. Reminiscent of the angst in some of Dolly’s early compositions like “Down From Dover” and “I’m Doing This For Your Sake”, the song tells the story of a young woman escaping domestic abuse at the hands of her father, who uses music as a means of dealing with her painful past. Once again, Rhonda & Darrin Vincent’s exquisite harmonies are a beautiful touch on a powerful story song, which anchored a Lifetime movie of the same title, starring Dolly. And she sings like a bird and she writes like a poet. Her voice has that high, lonesome sound. She hurts and her songs are the best way to show it, so the Blue Valley Songbird keeps traveling around.

“If We Don’t” – Dumplin’ (2018)

In 2018, Dolly Parton released the soundtrack for Dumplin’, an adaptation of Julie Murphy’s young adult novel of the same name. Produced by Linda Perry, the album featured a cavalcade of special guests (Mavis Staples, Miranda Lambert, Elle King, and more) and included new versions of six Dolly classics paired with half a dozen new songs co-written by Parton and Perry. “If We Don’t” is one of the fresh tracks, and it holds a beautiful and timely message. This call to “be the change we want to see” pairs Dolly Parton with bluegrass royalty and frequent collaborators – Alison Krauss and Rhonda Vincent (who also play fiddle and mandolin on the track, respectively). After Parton’s passing, this one should be a great reminder for all of us to be more like Dolly, because who will “if we don’t.”

“Walter Henry Hagan” (Live) – Heartsongs: Live From Home (1994)

I could have chosen any song from Heartsongs (my favorite Dolly album) for this list, and I contemplated several. That album is a masterpiece and a remarkable undertaking. It features a who’s who of the top names in bluegrass and beyond (Alison Krauss, Rhonda Vincent, Suzanne Cox, Carl Jackson, Jerry Douglas, Ron Block, and more) backing Dolly Parton for a live concept album in her beloved Smoky Mountains (as my friend Adam said, “What a flex!”). This sassy song (sassy Dolly is hard to beat) features Dolly telling off poor Walter for doing her wrong. There’s so much to love about this track: the a cappella intro, the soulful harmony singing, the killer pickin’, the audience’s exuberant involvement, Dolly’s Irish accent – I could go on and on. This one is so fun, and is one that our team loves to feature on the radio. You’ll be singing along in no time, and the scolding of “Walter Henry Hagan” will be stuck in your head all day!