March 18

Here are Songs by Jerry Jeff Walker That Showcased This Legendary Outlaw’s Incredible Talent

What’s great about Jerry Jeff Walker songs is that they are crafted to provoke the listeners to think deeper about the world. 

Born as Ronald Clyde Crosby in 1942 in Oneonta, New York, the legendary outlaw went by his stage name in the middle of the 1960s and performed in bands including The Tones and Circus Maximus prior to pursuing a solo career as a folk and country artist.

RELATED: Here Are Some Facts To See How Well Do You Know Jerry Jeff Walker 

Eventually, he left New York for the flourishing Outlaw Country scene in Austin, Texas, where he became one of the most important musicians to happen to the city. He brought Lone Star country-rocker form to its height in Texas, where he remained for the rest of his life.

And today, we’re going to dig a little deeper into some of Jerry Jeff Walker‘s best songs. Keep on scrolling below to see if your favorite ones made it to the list.

1. Mr. Bojangles

From: Mr. Bojangles (1968)

“Mr. Bojangles” showed how great of a storyteller Walker is. In the song, Walker unravels a story about a street performer he met during a brief stint in a New Orleans jail due to public intoxication in 1965. The homeless man goes by the moniker “Mr. Bojangles” to hide his true identity from the authorities. However, he was arrested following a police sweep of indigent people.

The two men, along with the other jail mates, talked about everything under the sun, but when Mr. Bojangles recounted a tale about his dog, the mood in the room instantly became heavy.

2. Pissin’ in the Wind

From: Ridin’ High (1975)

Perhaps you’ve heard this phrase many times about trying to do something when there is no hope of succeeding – and Walker sings about that, almost celebrating this lack of productivity. The song is all about people who may not have achieved that much but still proudly tell their grandchildren about their endeavors with a smile.

3. L.A. Freeway

From: Jerry Jeff Walker (1972)

Guy Clark – who was Walker’s fellow Texan songwriter – wrote the song after he had a disagreement with his landlord in Los Angeles, prompting him to move to Nashville.

And there’s no other outlaw who’s more fitting for this song than Walker, who also recently moved from New York to Austin, which he would later make his home. The song did well on the radio, helping Clark establish himself as a songwriter.

4. Up Against the Wall, Redneck Mother

From: Viva Terlingua (1973)

In “Up Against the Wall, Redneck Mother,” Walker pokes fun at the redneck stereotype that’s frequently been used to describe the state of Oklahoma as he sings about a man who can’t keep himself out of trouble. Yet, Walker explains that it’s not his fault that he often finds himself on the bad side because he was brought up that way, just like how a redneck would not have been in trouble if he wasn’t living in Oklahoma.

5. Gettin’ By

From: Viva Terlingua (1973)

“Gettin’ By” truly exemplifies how unique country music was in the 1970s. The song is about making the most of what you have and looking for ways to make it work for you, even if it isn’t exactly what you want or need.

6. Railroad Lady

From: A Man Must Carry On (1977)

The song tells the story of a man who met a woman with a history of having been in trouble. Still, the two of them do not really care what type of past each other has as their lust for each other is bigger.

7. Jaded Lover

From: Ridin’ High (1975)

Walker sings about a love gone wrong in “Jaded Lover,” which was a wildly popular theme in the 1970s. The song tells the story of a couple falling out of love, with one of them ending up watching the other move from one person to another in an attempt to find love. 

8. Sangria Wine

From: Viva Terlingua (1973)

Walker sings about his love for sangria wine, saying that “it’s organic and it comes from the vine.” He then expressed how much he loves drinking it as much as he can, especially with his old friends, and detailed the best way to enjoy it. 

9. Desperados Waiting For the Train

From: Viva Terlingua (1973)

This is another song written by Guy Clark, who said that he wrote it about his grandmother’s boyfriend named Jack, who was like a grandfather to him. The song skyrocketed when country music group the Highwaymen recorded it in 1985, bringing it to the No. 15 spot of Billboard’s Hot Country Songs chart.

10. I Feel Like Hank Williams Tonight

From: Live At Gruene Hall (1989)

Well, there’s no doubt that Hank Williams was one of the most well-loved artists in country music – and Walker was one of his biggest fans. In the song, Walker sang about the country legend both in a professional and more personal sense, at the same time paying tribute to his indelible impact in the genre.

More of Jerry Jeff Walker Songs From The Fantastic Outlaw Singer-Songwriter

Truly, Jerry Jeff Walker’s impact on the country and even rock music is indisputable. Here are some more of his hits that you need to check out.

  • Desperados Waiting for a Train
  • Driftin’ Way of Life
  • It’s a Good Night for Singing
  • Old Five and Dimers Like Me
  • Got Lucky Last Night
  • Stoney
  • I Makes Money (Money Don’t Make Me)
  • Her Good Lovin’ Grace
  • Comfort and Crazy
  • Like a Coat from the Cold
  • I Ain’t Living Long Like This
  • Morning Song to Sally
  • Little Bird
  • Hill Country Rain
  • Night Rider’s Lament

How about you? Which among Jerry Jeff Walker songs do you love the most?


Jerry Jeff Walker

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