George Strait

10. Amarillo By Morning

George Strait — Strait from the Heart

Anybody who has hit the rodeo road with a truckload of cowboys, saddles, and gear bags knows the feeling Strait so perfectly presents in this timeless road song. Gene Elder’s fiddle playing is as haunting as the winds of West Texas.

Willie Nelson

11. My Heroes Have Always Been Cowboys

Willie Nelson —16 Biggest Hits

Here is another song that simply could not be left off of our list. In its purest sense, not in the many commercials and videos it has been used in, this classic sums up the essence of the romance of the cowboy life for every kid who ever dreamed of heading West or who just watched the film “Electric Horseman.”


12. Prairie in the Sky

Mary McCaslin — Prairie in the Sky

It was a tough decision whether to include this version of the song or Tom Russell’s. But since we have another Russell song we tipped our Stetson to the original. McCaslin is another folk singer that consistently grabs the hearts of Westerners with her earthy romanticism. Sadly, she recently announced her retirement due to illness.


13. Tonight We Ride

Tom Russell — Indians Cowboys Horses Dogs

Many of Tom Russell’s story songs make you grab for the night latch and hold on for dear life. This songis no exception and tells the story of Black Jack Pershing and the hunt for Pancho Villa. By design it makes for a great road song.

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Bill Reynolds is a writer/publisher having worked in the Western lifestyle industry for more than 30 years. He has written five books and published several award winning magazines. He is principal at Alamar Media and

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