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.
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.
