Well I've got a CD of 'Old Saddle songs" that were origionally made way back when. Some before my time even. This is true cowboy music. Little Joe the wrangler, The onle about his sister. Streets of Larado, Strwberry Roan, My little Chapo, and many others. Othere then this true cowboy music there are a couple of artists I favor such as Michal Martin Murphy and Moe Bandy Dr. Railph Stanly ( blue grass) and the greatest of all Jimmy C. Newman and his Cajun music.

All of these are really good, but I think a couple of important ones were left off the list:

1. Shoulda Been a Cowboy- Toby Keith. This was my first favorite song and it still makes me really happy
2. Cowboy Take Me Away- Dixie Chicks. Cowboy love song. Reminds me of riding off into the sunset
3. Save A Horse, Ride a Cowboy-I forgot who sings it...Seriously, no one had this one on there? Haha

Mamma Dont let Your babies grow up to be cowboys
whatcha gonna do with a cowboy
caddilac Cowboy
Cowboy up
100% Cowboy
Cowboys Like Us
Good Ride Cowboy

Oh theres so many, I'll to think on it! But speakin' of Chris Ledoux I love the song "Good Ride Cowboy" by Garth Brooks that was wrote for Chris. ♥ And right now I'm listenin' to "Billy The Kid" by Chris. :D And of course I love "Cowboy Casanova" by Carrie Underwood. I'll post more soon. :)

I have to say that the best singers that have the moost "Cowboy" songs are Chris LeDoux, Garth Brooks, and George Strait. The best of all three tho is Chris. He was raised cowboy, sang cowboy, and was COWBOY thro and thro! His best songs are:
A cowboys got to ride
All around cowboy
All around cowboy of 1964
Cadillac Cowboy
Cowboy and the Hippy
Cowboy and the Rose
Cowboy in the Continental suit
Cowboy is a hell of a man
Cowboy like me
Cowboy songs
Cowboy Up
Cowboy's got to ride
Cowboy's prayer
Daydream Cowboy
Dirt and Sweat cowboy
Dream On Cowboy
Even Cowboys like rock & roll
Go riding Young Cowboy
God Must be a Cowboy
Hometown Cowboy
I don't want to be a cowboy anymore
Let's all help the Cowboys sing the blues
Life of a rodeo cowboy
Littlest cowboy rides again
Rodeo Cowboy
So you want to be a cowboy
Thank the cowboy for the ride
They couldn't understand my cowboy songs
This Cowboys's Hat
To old to play cowboy anymore
what More could a Cowboy need
Whatcha gonna do with a cowboy
Working cowboy blues
Wife behind the cowboy

these are all of the songs that i love by Chirs that have "cowboy" in them.

Damn, I plum forgot! One of the best songs I ever heard in my life, "a cowboy was born" by Chris Ledoux. That one gets to me every time I listen, one of the best ones out there for sure.

friends don't get me started on Chris Ledoux, I'll never finish. I can't say enough about that man, who he was and who he still is, at least for me.

I think my top 5 would be:
- The Cowboy Song (Don Edwards)
- Born To Be a Cowboy (MMM)
- Cowboy Up (Chris Ledoux)
- What More Could a Cowboy ever Need (Chris Ledoux)
- Airborne Cowboy (Chris Ledoux)

Chris was and still is "it" for me, plain and simple, truth be told.

Here's Hoping(There'll Always Be A Cowboy) by George Fox would be my pick

http://www.youtube.com/watch?v=ClfYCzugDT4

5. Cowboy’s Lament (Burl Ives, and Jewel)
4. Night Riders’s Lament (Garth Brooks and Susie Bogguss)
3. Cattle Call (Eddy Arnold)
2. Ride 'Em Cowboy (Roy Rogers)
1. Mammas Don't Let Your Babies Grow Up to Be Cowboys (Waylon & Willie)

Ok, I can not just list one song, so I'll list my top ten (not in order, but still a top ten);
How 'bout Them Cowgirls
Cowboys Like Us
The Cowboy Rides Away, By George Strait
Good Ride Cowboy, By Garth Brooks
A Cowboy's got to Ride
Cowboy in the Continental Suit
Whatcha Gonna do with a Cowboy
Cadillac Cowboy, By Chris LeDoux
My Heroes Have Always Been Cowboys, By Willie Nelson
The Cowboy in Me, By Tim McGraw

This could be a long list. In fact, a few years back I built a CD album based on this.

a few:

"This is the last cowboy song"
The Highwayman

"Are there any Cowboy's left?"
Lacy J Dalton

"American Cowboy"
The Sons of the San Juaquin"

"Coca-Cola Cowboy"
Mel Tillis

"I think I'd rather be a cowboy"
John Denver

I'd be happy to post more if anyone wants to see the list.

My favorite would have to be one by Kevin Banford called Cowgirls rodeo. Its in the Hallmark Movie "Straight From The Heart". Great song!