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There have been a lot of good Cowboy songs that were written and sung through the years. Some of the great ones's were "Happy Trails To You " written by Dale Evans and sung by Roy Rogers and Dale Evans. Then there was Gene Autry singing "Back in the Saddle Again."Another one that comes to mind is "Wild Fire" sung by Michael Martin Murphy. But the one that really grabs me is the song called "I Should Of Been A Cowboy" sung by Toby Keith. I have several of his CD'S and I listen to that song all the time. I love the lyric's. Especially the part of the song where he refers to (Steal'n A Young Girl's Heart Just Like Gene and Roy). If you never heard the song or his music, then I recommend you go buy it. s

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I enjoy Seven Spanish Angels by Willie Nelson
I was in Tombstone one evening and heard Johnny Bencomo sing "Streets of Laredo." He brought tears to my eyes. It is considered an old cowboy song, but the melody apparently comes from a centuries old Celtic funeral march. There are many more verses in the song than the two or three we normally hear from other performers.

Johnny is unusual in that he likes to recite a bit of history to go along with the songs he sings. Did you know that "El Paso" is based on a real event?
IMHO, The best cowboy singer by a country mile is Don Edwards.


http://www.donedwardsmusic.com/
While I love the old stuff, there are several more modern songs that I think do a pretty good job of capturing the essence of the cowboy. "Horses and Cattle" and "Johnson County War" by the late Chris Ledoux come to mind. Also "Pierce" and "The Last of the Red Rock Riders" by Brenn Hill. I would even include...take a deep breath... Garth Brooks' version of "Cowboy's Lament". Did that come from Ian Tyson?

Dessie Marie
Most anything by Ian Tyson works, but my favourite has to be Ed Bruce's "Last Cowboy Song".

http://www.youtube.com/watch?gl=GB&hl=en-GB&v=GKeDcF1v_Y4&a...
This is indeed my all-time favorite. No other song I know evokes the true loss of an American cultural tradition, and a set of values that really ended in the 1950's, IMHO.
Like other such questions, one must determine what is meant by "best."

IMO, the most anthentic are the old ones, like those I posted in the "Fans of 19th Century music" group.

In todays market, I would have to vote for Don Edwards, Sons of the San Jouquin, Red Steagal, and Michael Martin Murphy. Iand Tyson and Chris Ledoux are good, but they sing more contemporary type music.

One must keep in mind there is a vast difference between today's country music and true western music. It used to be "country and Western" back when I was growing up, but now the two have seperated.

Here's something I wrote about that:

WESTERN MUSIC

Who took the “W” out of Country and Western?
Who pushed that music aside?
Who hired these “New Country” singers?
Talented, but probably can’t ride

A cowboy singer is one who’s been there
Knows about riding the range
Keeps his horse nearby and his saddle clean
And work, he does not find strange

Now I’m not knocking the country singers
Wouldn’t say any bad words like that
But you ain’t necessarily a cowboy
Just cause you got boots and a hat

Some spent the riches they’ve made
Buying a cowboy ranch for a fling
But buying something and being something
Can be a totally different thing

Now days I miss Gene Autry
Roy and The Sons of the Pioneers
Tex Ritter singing “Rye Whiskey”
Why, I haven’t heard that one in years

We do have some talent out there
There’s some with a pretty big name
But you’ll never hear them on the radio
For that, who else can we blame?

Like many, we set back in silence
Let others decide what to show
But I want the chance to listen
To a tune about a wrangler named Joe

Or “The Strawberry Roan” or “Laredo”
Or “When the work’s all done this fall”
And I still always get sorta’ misty eyed
When I hear “The Master’s Call”

Now I don’t mean to impose
To push my taste in music on others
But I’d prefer to listen to cowboy music
That is, if’n I had my ‘drothers

S.E. Hutchison
2/2002
Ian Tyson ain't too shabby
Let's not forget about Ken Curtis and the Sons of the Pioneers, singing Tumbling Tumbleweeds or Marty Robbins singing Strawberry Roan and although we generally think of him as a country singer, Seven Spanish Angels and Pancho and Lefty by Willie Nelson are hard to beat!!
Willie Nelson and Marty Robbins are great but don't forget Dave Stamey, I love his music. If I Had a Horse and The Bandit Joaquin are my favorites.
Is there a CD compilation of authentic Western songs, i.e. tunes that would've been sung around the fire or bunkhouse before the turn of the 20th century?  I'm researching a novel right now and would be grateful if someone could point me in the direction of some period music.
Tex Ritter did an album shortly before he died that contained a lot of old cowboy songs, including Rye Whiskey, Blood on the Saddle, Little Joe the Wrangler, & When The Work's All Done This Fall. Rex Allen did one called Hairy Legged, Boney Kneed Cowboy Songs, which included Tyin' Knots In The Devil's Tail. A friend of mine, Mike Blakely, has a couple of CDs of old cowboy songs, & he writes & sings 'new' cowboy songs in the old tradition, including one called The Horses In My String. He's on the web--look him up.

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