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Top 49 Best Bluegrass Songs of All Time

Some genres of music are particularly related to one geographical area. Bluegrass is one of those. It had its beginnings in the Appalachian Mountains in the 1940s. But, since those early days, it has spread to an international audience.

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Unlike some other musical genres, Bluegrass is traditionally played on acoustic and not electric instruments. Although, there are some occasions when electric instruments are used to great effect, as we shall find out later.

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The Roots Spread Wide

Like all music, there are influences, and roots, from where the styles are derived from. Bluegrass has its roots thousands of miles away from the mountains it is associated with. 

Traditionally, it was derived from English, Scottish, and Irish folk ballads. As time has moved on, it now also has some Jazz and Blues influences. However, in many ways, it is still a unique genre. One way it is the same as other genres of music relates to the musicians. 

All genres are developed by musicians, and Bluegrass is no exception. Guitarist Lester Flatt and Earl Scruggs on the banjo both helped to define Bluegrass in the early days. Others have followed. So, let’s take a look at some of the best Bluegrass songs we have heard over the years, starting with…

Best Bluegrass Songs

Top 49 Best Bluegrass Songs of All Time

1 Dueling Banjos by Eric Weissberg With Steve Mandell

Let’s start with a well known Bluegrass song from the 1972 film “Deliverance.” Whether you liked the film or not, the “Dueling banjo” scene was excellent and at the same time a little strange. The tune was written by Arthur Smith in 1954, and he called it “Feudin’ Banjos.”

Including it in the film caused a lawsuit found in favor of Smith as the film company hadn’t asked permission to use it. It was subsequently issued as a single with credit to Smith and went to #2 on the American chart.

For those people all around the world who had never even heard of Bluegrass music, let alone heard any Bluegrass songs, this was their introduction to it.

2 The Devil’s Train by The James King Band

James King is well-known in Bluegrass circles, having played with most of the top performers. He was nicknamed the “Bluegrass Storyteller” as he was able to mix music with real stories. 

This particular song is taken from his album, Three Chords And The Truth. It is a typical upbeat Bluegrass song with plenty going on.

3 Blue Moon Of Kentucky by Bill Monroe And His Bluegrass Boys

Bill Monroe was the man credited with starting the rise of Bluegrass music. He was an important figure, recognized in Country music circles. He helped to bring back the mandolin as an important instrument and was an excellent player himself.

This song is a waltz, and it has an interesting history. Bill Monroe wrote it, and he and his band recorded it in 1946. It was an instant success. However, in some circles, it is remembered and known in other ways.

It was Elvis Presley’s first single, released in 1954. He performed it in a much more Rockabilly style, as you might expect. Not quite “Jailhouse Rock,” but his first step on the ladder. He also put it on a 1959 album, A Date With Elvis.

4 Little Birdie by Wade Mainer

This is a song that, in its original format, goes back a long way. It was first recorded by John Hammond in 1925, but this version by Wade Mainer came out in 1951. This popular Bluegrass song has since been covered by plenty of Bluegrass singers.

It is a story of someone wanting a better life than they have; at the time that this song was written, that sentiment was probably very relevant.

5 Country Girl by Carolina Chocolate Drops

Now, this is an interesting track to comment on. The Carolina Chocolate Drops are an all African-American Bluegrass trio. This particular track is taken from their album, Leaving Eden.

I was going to make the point that they wouldn’t get away with that name today, given their ancestry. But then I noticed that this is their fourth album, released in 2012. I am not sure what is going on there.

So, I had to try and find out why they would call themselves that, as my initial thought was that it was rather derogatory. I found that they named themselves in homage to a band from Tennessee from the 1920s. They were called the ‘Tennessee Chocolate Drops,’ and they were all African-American.

The Music

Let’s get back to the music, which is excellent. Probably the best Country/Bluegrass group I have heard. Excellent musicianship and a singer with a great voice. If you want some of the best modern Bluegrass music, then this is for you.

6 Foggy Mountain Breakdown by Lester Flatt And Earl Scruggs And The Foggy Mountain Boys

If you are going to talk about the best Bluegrass songs, then sooner or later, the names of Lester Flatt and Earl Scruggs will come up. They are two of the most respected musicians in Country and Bluegrass music.

You will recognize this song…

Even if you are not a listener of Bluegrass music, you will probably recognize this. It was used in the film “Bonnie and Clyde.” 

This is the original 1949 version which is played very quickly. Included here to allow you to hear the musicianship involved. It will probably go down as one of the best instrumental Bluegrass songs ever.

7 Mountain Dew by Grandpa Jones

Louis Marshall Jones, otherwise known as Grandpa Jones, was thirty years old when they cut his first acetate recording. But, even by then, he was already being called “Grandpa.” 

This was because when he spoke, they thought he sounded like an old man. The name just stuck with him throughout his career. He certainly played up to the image created. Of course, in later life, he grew into the name.

Reminds me of those old Western films… 

There would always be someone selling a potion from a wagon that cured everything. This song is about a magic concoction, so maybe that is where he got the idea from. An interesting character, when he sang his songs, he was very much a member of the old “hee-haw” club.

8 Nine Pound Hammer by Johnny Cash

It shouldn’t come as a surprise that the “Man in Black” turned his hand to a bit of Bluegrass. Although, he does perform it in his own inimitable style. “Nine Pound Hammer” is a well-known song recorded by plenty of people. It has the same storyline as a similar song, “Take This Hammer.”

Johnny Cash released the song in 1963 as part of his album, Blood, Sweat & Tears. The song was first recorded in 1927 and has been a favorite Bluegrass song ever since.

9 Rocky Top by The Osborne Brothers

This is a song written by Boudleaux and Felice Bryant. If you recognize the names, it is because they were a well-known husband and wife songwriting team. They were responsible for writing “Bye Bye Love” and “Wake up Little Susie” for The Everly Brothers, amongst others.

“Rocky Top” was released in1967 and is about a small town in Tennessee. It was taken from the album, From Rocky Top to Muddy Bottom.

It was first released as a single in 1967 by the Osborne Brothers. Since then, it has been recorded on dozens of occasions by other artists. It has been made one of Tennessee’s state songs.

The Song

…is a simple enough story and one that will be familiar to some. It talks about missing the simple life of their small village, which they left to go and work in the city.

It sold well enough to get a listing on the American Country music chart, as did a later version by Lynn Anderson in 1970. A song that immediately resonates with the people who live in that part of the world.

10 Wagon Wheel by The Old Crow Medicine Show

This, of course, is one of the most famous Bluegrass songs. It has, in the eyes of some, been overplayed. But, you can’t dispute it is popular and well-liked. 

It was co-written by Bob Dylan, who laid down the chorus in 1973. That was part of the original recordings for his album, Pat Garrett & Billy the Kid.

Never released on the album…

But, it appeared on a bootleg and was called “Rock Me Mama” after a line in the lyrics. That lyric came from a Big Bill Broonzy song recorded in 1928.

Verses were added by Ketch Secor of The Old Crow Medicine Show in 1998. This track is taken from their album, Old Crow Medicine Show, released in 2003. Its popularity as a song has grown, which means that the band’s popularity has as well.

11 Jumbo by The Punch Brothers

Bluegrass musicians and their fans tend to be rather traditional. Therefore, The Punch Brothers seem to be an anomaly in their midst. I don’t know if there is such a thing as a “Progressive Bluegrass band,” but if there is, then the Punch Brothers are it.

The Punch Brothers are a five-piece brought up with Bluegrass music around them. They retain the basic elements that make up Bluegrass and its sound. But, they also include what you might call influences that are “non-bluegrass.”

“Jumbo” was taken from their album, All Ashore. The album is worth a listen as it demonstrates some new ideas within the genre. You will hear some Jazz influences and contrasting rhythms, and the songs range from uptempo to some creative ballads.

12 Dust in a Baggie by Billy Strings

This was a song that was released in 2013 on the album Rock of Ages. “Dust in a Baggie” is slang for cocaine. 

The singer is bemoaning the fact that he has gone off the rails because of it. He is going to be sitting in his prison cell for twenty years, wondering where it has all gone. 

Not too hard to work that one out, fella…

This is a classic style driving bluegrass rhythm track that you would be expecting to hear. However, on a later album, Home, he moves into slightly different Bluegrass styles. 

He draws influences from Pink Floyd, Led Zeppelin, and even Jimi Hendrix. Does that fit with Bluegrass? You will have to listen and decide.

13 Looking In The Eyes Of Love by Alison Krauss with Union Station

This was a track from her album working with Union Station called So Long So Wrong, released in 1997.

Alison Krauss joined up with Union Station not long after releasing her first album, Too Late To Cry, at age 16 in 1987. She has since alternated making an album with them and then a solo album.

A talented piano and fiddle player and songwriter, “Looking In The Eyes of Love” is a move away from her traditional Bluegrass sound. It is a tender ballad that shows another side of her and the band. It was covered by the Irish band, The Corrs on their album, In Blue.

14 Wayfaring Stranger by Emmylou Harris

Emmylou Harris is, of course, a well-known Country singer. So it isn’t surprising she has the odd Bluegrass song in her repertoire. This one, though, is a little different in that it is a thoughtful slow tempo song.

She is a singer who was inspired by the music of Pete Seeger, Bob Dylan, and Joan Baez. So much so that she dropped out of college to pursue a music career.

One of the most widely respected country singers…

And she wasn’t afraid to work with other artists. Mark Knopfler is an example where Balcony Of Love was just one of the albums they released together.

This particular track is taken from her 1980 album, Roses in the Snow. The album reached #26 on the American chart.

15 The Devil Went Down to Georgia by The Charlie Daniels Band

To finish my list of the best Bluegrass songs, let’s look at a track some might argue isn’t Bluegrass at all. The reason they say that is because the instruments are amplified and electric. As I said earlier, Bluegrass was traditionally acoustic-only.

But remember… 

Those traditions arose when there wasn’t much in the way of electric guitars or ways to amplify a fiddle. We have moved on a bit since then. I agree with many commentators; this is Bluegrass rocking along at its best with some great musicianship.

“The Devil Went Down To Georgia” was released in 1979 and taken from their album, Million Mile Reflections. The story is a variant of the age-old tale of the devil trying to buy the soul of a young musician in return for a favor. It has certain similarities to the film “Crossroads.”

As in the film… 

The devil and the young musician, Johnny, swap solo breaks in impressive style. It had success on both sides of the Atlantic, reaching #14 in the UK and #3 in America.

No doubt it is a great track and worthy of being the last on this list. If you’re looking for a song to show off a more modern Bluegrass style, then you won’t find much better than this.

16 Man of Constant Sorrow by Soggy Bottom Boys

17 I Am a Man of Constant Sorrow by The Stanley Brothers

18 Angel Band by The Stanley Brothers

19 Blue Ridge Cabin Home by Flatt & Scruggs

20 Orange Blossom Special by Bill Monroe

21 Roll in My Sweet Baby’s Arms by Flatt & Scruggs

22 Will the Circle Be Unbroken by The Nitty Gritty Dirt Band

23 Uncle Pen by Bill Monroe

24 Fox on the Run by The Country Gentlemen

25 Foggy Mountain Top by The Carter Family

26 Long Black Veil by The Country Gentlemen

27 Shady Grove by The Kentucky Colonels

28 Cripple Creek by The Dillards

29 Sitting on Top of the World by Doc Watson

30 Soldier’s Joy by Ricky Skaggs

31 Old Home Place by J.D. Crowe & The New South

32 Blue Moon of Kentucky by Elvis Presley

33 The Fields Have Turned Brown by The Stanley Brothers

34 John Hardy by The Carter Family

35 The Ballad of Jed Clampett by Lester Flatt & Earl Scruggs

36 My Home’s Across the Blue Ridge Mountains by The Carter Family

37 Clinch Mountain Backstep by The Stanley Brothers

38 In the Pines by The Louvin Brothers

39 Little Maggie by Ralph Stanley

40 Nine Pound Hammer by Flatt & Scruggs

41 Foggy Mountain Rock by Flatt & Scruggs

42 I’ll Fly Away by Alison Krauss

43 Rawhide by Bill Monroe

44 Bluegrass Breakdown by Bill Monroe

45 East Virginia Blues by The Stanley Brothers

46 Bluegrass Stomp by Bill Monroe

47 Rank Stranger by The Stanley Brothers

48 Midnight on the Stormy Deep by The Stanley Brothers

49 The Rocky Road to Dublin by The Chieftains ft. The Nitty Gritty Dirt Band

Looking for More Incredible Music?

Well, then take a look at our detailed articles on the Best Banjo Songs of All Time, the Best Songs of The 2000s, the Best 70s Rock Songs, the Best 90s Country Songs, and the Best Funny Songs of All Time for more fantastic song selections.

Also, you’ll want to hear those songs. So, check out our in-depth reviews of the Best Wireless Bluetooth Headphones, the Best Headphones for Music, the Most Comfortable Headphones, and the Best Headphones Under $200 you can buy in 2023.

And, don’t miss our comprehensive reviews of the Best Sound Quality Earbuds, the Best Noise Isolating Earbuds, the Best Earbuds for Running, and the Best Bass Earbuds currently on the market.

Best Bluegrass Songs – Final Thoughts

It doesn’t matter whether you come from the Appalachians or not. Bluegrass is still great music for getting a party going and for letting your hair down a bit. And it also demonstrates some great musicianship, something that we all can appreciate.

Until next time, happy listening.

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About Joseph L. Hollen

Joseph is a session musician, writer, and filmmaker from south Florida. He has recorded a number of albums and made numerous short films, as well as contributing music to shorts and commercials. 

He doesn't get as much time to practice and play as he used to, but still manages (just about!) to fulfill all his session requests. According to Joseph, it just gets harder as you get older; you rely on what you learned decades ago and can play without thinking. Thankfully that's what most producers still want from him.

He is a devout gear heat and has been collecting musical instruments all his life. As his wife, Jill, keeps on saying, "You're very good at buying nice instruments, but terrible at selling them!".

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