In no particular order:
Complete soundtrack of BBM
Please remember me by Tim McGraw
My old friend - Tim McGraw
Everything I own - Bread (I think nobody has mentioned this one so far; I L O V E it)
Wyoming Skies
Not a day goes by - Lonestar
Desperado - Eagles (and only by the Eagles! Edtit: nope, not true; I also like the German version by Udo Lindenberg))
Can't cry hard enough
Two Cowboy Walz - Mark Weigle
Cowboys are frequently, secretly - Willie Nelson
Far Away - Nickleback (still one of my absolute favs; how happy were the times when it was a hit and played regularly at my local radio station))
A Cowboy's born with a broken heart
Streets of Laredo
A song that tells the story of an involuntarily bull rider; he was listed to the wrong event at a rodeo, and in the end says "never again" (something along this line). I can't remember title or artist right now. (perhaps Chris LeDoux?)
Edit:Yup. Sure is Chris LeDoux, and the song's title is Bull Rider.
Song of Wyoming
Coyotes (this one took me a while to get used to, at first I didn't like it much, but now I do)
Always on a mountain when I fall
Hal Ketchum - Past the Point of Rescue
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I'm sure there are more which I can't think of right now.
What I don't like are the instrumental ones (except for the soundtrack). I think of Bruce Kaphan and similar things (
Hamrock? Hammock) here.
And I was happy to see the old BBM radio icon in your post. I really miss it. I like it ten times more than the current one.
Thank you for this poll Eric