If you'll excuse the expression, it wasn't always depressing in the Depression years. Rural Americans — including Okies — enjoyed music just as much as the sophisticates in the big cities, but their choices were a little different. They liked gospel, bluegrass, and folk music, all loosely fitting under the heading of country music. People enjoyed playing, singing, and dancing at all kinds of gatherings, and music was definitely a part of their lives.
One thing there's little doubt about - the musician who was eventually most identified with the dust bowl saga not only wrote and performed songs about it, he also lived it. Although he didn't actually gain much fame until the 1940's and later, Woody Guthrie was the best-known musical storyteller of the Depression years.
He grew up in Oklahoma, and for years traveled America on the hobo trail, listening to the people and their music. A lifelong socialist who often drew controversy, he felt he was the voice of the underprivileged, and his legacy influenced many later musicians. These include his son Arlo, and Bob Dylan, who acknowledged his inspiration by writing and performing songs about Guthrie.
Woody's biggest hit, "This Land Is Your Land", is probably the one most remembered now, but he wrote and performed a number of songs about the dust bowl struggles. (He even wrote a song called "Tom Joad," the main character in The Grapes Of Wrath, played by Henry Fonda in the film.)
One of the best, from his album Dust Bowl Ballads, is "Dust Bowl Refugee," and this video of another:

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Article comments
1 - Howard Dratch
Big Geez. That was a wonderful article on one of America's musical treasures. Guthrie, Pete Seeger, Arlo, Dylan, Baez. It is amazing how happy the emotionally-charged protest songs can make us now that the world has turned and we have new problems for people to sing about, photograph and make movies about. Did I really say "new"? Now that the old problems have been repackaged.
Your ode to Guthrie was great and the YouTube selection one of the first I have emailed myself. Great pictures of Woody I hadn't seen and those fantastic FSA (Farm Service Administration) pictures that saved a view of the country at a crossroads of its history.
Wonderful piece. Great music. Memorable images.
2 - Big Geez
Appreciate the praise and the thoughtful comments, Howard.