Celebrate the Heart of Country, Americana, and Roots Music!

Drop Us A Line, Y'all

Y'all interested in advertising, partnering up, contributing stories, joining our team, or just got a question? Well, don't be shy, drop us a line!

Follow Us

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

Jerry Jeff Walker Songs
by
  • Arden is a Senior Country Music Journalist for Country Thang Daily, specializing in classic hits and contemporary chart-toppers.
  • Prior to joining Country Thang Daily, Arden wrote for Billboard and People magazine, covering country music legends and emerging artists.
  • Arden holds a Bachelor of Arts in Journalism from the University of Tennessee, with a minor in Music Studies.

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?

Trending

Latest Stories

Hannah Kay Honors Loretta Lynn in Powerful "Coal Miner's Daughter" Performance

Hannah Kay Honors Loretta Lynn in Powerful “Coal Miner’s Daughter” Performance

In a world where country music continually evolves, some voices remind us of its timeless roots. In 2019, then-18-year-old Texas singer Hannah Kay did just that with her moving rendition ...

Zach Top’s Journey from Farm Life in WA to Breakout Country Music Star

Zach Top’s Journey from Farm Life in WA to Breakout Country Music Star

Zach Top didn’t just stumble into country music fame; he built his way there from the ground up, starting on a modest farm in Sunnyside, Washington. Far removed from Nashville’s ...

Morgan Wallen’s “Love Somebody” Tackles Real Romance with a Fresh Sound

Morgan Wallen’s “Love Somebody” Tackles Real Romance with a Fresh Sound

Morgan Wallen’s new single, “Love Somebody,” has arrived, and it’s not just another love song—it’s an honest look at the complicated, often bumpy road to finding real connection. After years ...

Morgan Wallen Sets New Records Outshining Dolly Parton and Taylor Swift

Morgan Wallen Sets New Records Outshining Dolly Parton and Taylor Swift

Morgan Wallen’s career continues to reach impressive heights with his latest achievement. This historic milestone solidifies his place among country music’s most celebrated figures. His new single, “Love Somebody,” has ...

Jelly Roll Gets Emotional Sharing a First Look at His Expansive 500-Acre Dream Property

Jelly Roll Gets Emotional Sharing a First Look at His Expansive 500-Acre Dream Property

Country music star Jelly Roll recently shared an emotional video on social media, revealing his purchase of a sprawling 500-acre plot of land. The video, filled with raw emotion and ...

Morgan Wallen Donates $500,000 Worth of Musical Instruments to Students Across the Nation

Morgan Wallen Donates $500,000 Worth of Musical Instruments to Students Across the Nation

Country music superstar Morgan Wallen isn’t just wowing crowds on his One Night at a Time tour; he’s also rocking the world of music education. Through his Morgan Wallen Foundation, ...

Luke Combs and Eric Church's Concert Raises $24M for Hurricane Helene Victims

Luke Combs and Eric Church’s Concert Raises $24M for Hurricane Helene Victims

Country music superstars Luke Combs and Eric Church united for a powerful cause, headlining the “Concert for Carolina” to benefit victims of Hurricane Helene. The star-studded event, held at Bank ...

13 Surprising Facts You Probably Didn’t Know About Brad Paisley

13 Surprising Facts You Probably Didn’t Know About Brad Paisley

When you think of Brad Paisley, you probably picture the quick-witted country star with a guitar in hand and a string of chart-toppers behind him. But there’s much more to ...

Blake Shelton Honors Elvis Presley with "Suspicious Minds" Cover

Blake Shelton Honors Elvis Presley with “Suspicious Minds” Cover

Elvis Presley’s influence on music is undeniable, and his legacy inspires generations. His 1969 hit “Suspicious Minds” remains a signature track, capturing love, conflict, and heartbreak themes. Decades later, country ...

Alan Jackson Stops "Pop a Top" at CMAs in Honor of George Jones

Alan Jackson Stops “Pop a Top” at CMAs in Honor of George Jones

It’s always remarkable when country legends support each other, especially on music’s biggest stages. Alan Jackson’s unforgettable tribute to George Jones at the 1999 CMA Awards was one such moment, ...