25 Best Bluegrass Songs of All Time - Music Grotto (2023)

Whether you were raised in the Great Smoky Mountains or not, the spirit of Bluegrass can touch a basic yearning nostalgia that will pull at the heartstrings of people all over the world.

I’ve compiled a list of the 25 best Bluegrass songs to either bring you back or introduce you to the wide world of Bluegrass music.

Without further ado, here are the top picks.

1) Dueling Banjos – Eric Weissberg with Steve Mandell

This has to be one of the most iconic songs of the 20th century due to its appearance in the cult classic movie Deliverance. You should see the magic of cinema and music combined to an evocative perfection that will convert any nonbeliever to marvel at the magic of Bluegrass.

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2) Nine Pound Hammer – Tony Rice

This classic bluegrass song was originally recorded in 1927 and has been a favorite ever since, played with pride by dozens of artists including the world-renowned Johnny Cash.

3) Tennessee 1949 – Larry Sparks

Considering Larry Sparks was only a toddler in 1949, it’s ironic how well he conveys nostalgia for his youth! I suppose it doesn’t matter when your glory days were, you can certainly relate to the lyrics and the fun in this upbeat tune that honors the good old days.

4) Man Of Constant Sorrow – Stanley Brothers and Soggy Bottom Boys

This song was originally written and performed by the Stanley Brothers, but we have to give it to the Soggy Bottom Boys for their version that became an international sensation through the widely acclaimed Cohen Brother masterpiece O Brother Where Art Thou.

5) I’ll Fly Away – Alison Krauss and Gillian Welch

Yet another beautiful song showcased in the film and soundtrack, Oh Brother Where Art Thou, I’ll Fly Away is also a favorite, other-worldly song sung at funerals for its comforting imagery of flying away to meet the creator.

6) I’ll Meet you in Church Sunday – Bill Monroe

Sung by the father of Bluegrass himself, the honorable Bill Monroe, this song is a classic mandolin-picking, harmonizing, God-fearing example of what Bluegrass is for us all.

7) Foggy Mountain Breakdown – Lester Flatt and Earl Scruggs and the Foggy Mountain Boys

I chose the original, fast-paced version of this 1949 instrumental classic. It gives Dueling Banjos a run for its money in terms of best instrumental Bluegrass recording of all time.

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8) With Body and Soul – Bill Monroe and His Bluegrass Boys

Bill Monroe puts heart and soul into this romantic song about the wholehearted love of a woman. This would be a good pick for a wedding, anniversary, or Valentine’s Day tune for your sweetheart.

9) Rocky Top – The Osborne Brothers

Released in 1967, this homage to a small town in Tennessee earned its recognition from the state of Tennessee as one of their official state songs in 1982.

10) Blue Moon of Kentucky – Bill Monroe and His Bluegrass Boys

You might think this is an Elvis song, and you’d be right. But it was a Bill Monroe song first! Written and recorded by Bill Monroe and the Bluegrass Boys in 1946, this song became an instant hit that was later recorded by Presley as his very first single in 1954.

11) Mountain Dew – Grandpa Jones

Could this be the inspiration for the neon green soft drink that was all the craze in the ’90s? Who knows, but it certainly could be judging by the lyrics of this song about a magic concoction that heals whatever ails you.

12) I Found a Hiding Place – Carl Story and His Ramblin Mountaineers

Whether you’re religious or not, this call and response church song is as comforting and catchy as can be. Carl Story is one of a kind and an original Bluegrass genius whose combination of Bluegrass and religious music earned him the title of Father of Bluegrass Gospel.

13) Tortured Tangled Hearts – The Dixie Chicks

We’re not just featuring the Bluegrass classics on this list of great Bluegrass music. Bluegrass continues to inspire new artists to create. You’d be hard-pressed to find someone who doesn’t know who the Dixie Chicks are.

14) Devil’s Train – James King Band

This upbeat song is one in a long line of hits from storied Bluegrass musician James King who has played with the likes of the Stanely Brothers, Clinch Mountain Boys, the Johnson Mountain Boys, and many more.

15) I’m On My Way Home – Bill Monroe and his Bluegrass Boys

No one can deny their roots, and this song sums up what it means to go home. If there’s one thing Bluegrass has mastered, it’s the art of nostalgia.

16) Meet Me By The Moonlight – The Stanley Brothers and the Clinch Mountain Boys

All Stanley Brother’s songs have beautiful harmonies, but this one also has spectacular fiddling between the singing parts.

17) Little Birdie – Wade Mainer 1953

This classic 1950s recording of Wade Mainer’s Little Birdie was recreated by many Bluegrass stars who came after him. Most of us can relate to wanting a different life than the one we have right now, and this song drives that sentiment home.

18) Walls of Time – The Johnson Mountain Boys

This heartfelt tribute to the mountain home was written by Bill Monroe, but the soulful deliverance by the Johnson Mountain Boys is our preferred version.

19) I Saw the Light – Roy Acuff with The Nitty Gritty Dirt Band

The Nitty Gritty Dirt Band is proof that Bluegrass doesn’t have to originate in the great Appalachian region. This band hails from California!

20) Long Black Veil – John Duffey

This slow, country ballad is the kind of song you’d hear in an old western bar when the drinking turns sentimental amongst a group of good ‘ol boys.

21) High Lonesome Sound – Vince Gill

Bluegrass goes electric with this modern fusion of country music. There may be drums and electric guitars, but the banjo solos and classic Bluegrass harmonizing maintain a classic Bluegrass sound.

22) Last Train to Kitty Hawk – Balsam Range

Balsam Range is a relatively new Bluegrass band whose albums and singles have given them wide notoriety, reaching the top of the Bluegrass charts since their inception.

23) Girl at the Crossroads Bar – The Bluegrass Cardinals

This may be a classic take on a bluegrass original from Larry Sparks, but this L.A. native Bluegrass band deserves some love.

24) Georgia Buck – Carolina Chocolate Drops

This band breaks all the molds as the only all-Black bluegrass group I’ve ever heard of. They also happen to be my favorites. Enjoy!

25) Wayfaring Stranger – Emmylou Harris

This song showcases Harris’s hauntingly beautiful voice. Famed musician Jack White of the White Stripes sang a version of this song in the famous novel turned movie Cold Mountain.

Well, there you have it. Hailing from the Appalachian region, Bluegrass music has made its mark worldwide and has churned out some of the most iconic songs in the industry.

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