Nice guy. I had a birthday party on his show in the 50s. He was hardly a cowboy. But played his own guitar and sang songs I still remember.
The Wreck of the Old 97.
Ivan Skavinsky Skavar.
Many others.
The Three Amigos!
I was always a Gene Autry fan myself.
You’ve mentioned that before, and I’m still envious. I wonder if my mother ever even sent those postcards in.
Chris LeDoux.
Saw his old backing band, Western Underground, over the summer. They’re essentially a tribute band now, but they have some new material too. It’s pretty good.
“Haaa…”
Most definitely, considering the influence he had on popular music. Although he wasn’t much of a singer himself.
Times Square’s [url=http://www.nakedcowboy.com/]Naked Cowboy** still rates high with me!
But my top singing cowboy will always be the purest, funniest, and most talented of the bunch. Here’s to Richard “Big Dick” Kinky Friedman!
Thought of him too. Unlike most of the others in this thread, Chris was an actual (competitive rodeo) cowboy. Influential, too: Garth Brooks, possibly the biggest country music star of all time, said that everything in his live show that was any good, he probably stole from Chris LeDoux. 
Apparently, there were real singing cowboys.
Cowboys who could sing and play an instrument were paid better on long hauls and trail drives because they were not only workers, but entertainment, which is a thing when you’re all out in the middle of nowhere. That, and apparently, the music tended to soothe the cattle, which is important when your worst nightmare is a stampede…
I’m sure there were singing real singing cowboys. There are real singing waiters, bus drivers, cops, and people in all professions. Generally if they keep their jobs it means they are entertaining others. However, I am curious if you have some sort of cite about the singing soothing the cattle. This could be true, but I’m wondering if cattle appreciate music any more than any sound that doesn’t seem to be a predator.
Even if it wasn’t true, so long as the ranchers thought it was true, or the singer could convince the owners of that, it would still mean more demand for the singers.
I should mention that Ian Tyson (as in Ian & Sylvia) was also a real rodeo cowboy- he earned his hat honestly.
Well, any farmer will tell you that slow, rhythmic, calming tones will tend to soothe cattle. They’ve even tried piping music into milking barns for that reason. I picked up the info from a book I read, but durned if I could cite it now… call it anecdotal.
But apparently, the cowboys believed it.
A wonderful book on the singing cowboy was written by Doug Green, better known as “Ranger Doug” of Riders in the Sky mentioned early on in this thread. It is well-written and goes into almost every aspect of the genre. If you are even mildly interested in the subject, you will enjoy this book.
I should mention the only known (by me at least) all midget cast of a western, 1938’s The Terror of Tiny Town, featured the hero as a singing cowboy.
Well, at the time it was made, movies featuring singing cowboy heroes were not at all uncommon.
Movies with an entire cast under four feet tall, on the other hand…
Cattle drives with…
Control Group: No music
Group A: Singing cowboys
Group B: Bagpiping cowboys
Group C: Vuvuzeling cowboys
I am here to tell you that if I hired on as the chuckwagon driver for your cattle drive, I could certainly stand, in the evening firelight, to hear a talented cowboy play the guitar and sing “Ghost Riders In The Sky.”
I am here to tell you that if I hired on as the chuckwagon driver for your cattle drive, I could certainly stand, in the evening firelight, to hear a talented cowboy play “Alamein Dead” on the bagpipes.
But I am also here to tell you that after a night or two of listening to ANY damn thing on the vuvuzela, I’d beat the cowboy in question to death with his own instrument and bury him and it on the lone prairie with a harsh look and a muttered, “We will not speak of this again.”
And I don’t care WHAT the damn cattle think.
Lee Marvin.
End of debate.
Classic era: Rogers/Sons.
Country rock era: New Riders of the Purple Sage and Commander Cody and His Lost Planet Airmen.