The 10 Best Jerry Jeff Walker Songs of All-Time

Jerry Jeff Walker

Singer and songwriter Jerry Jeff Walker might have been best known for a song he wrote called “Mr. Bojangles” in 1968, but that certainly isn’t his only claim to fame. As a matter of fact, he performed for many years, singing and writing a number of notable songs. Many people credit him with starting the outlaw movement that became so popular in country music during the 1970s and 80s. Whether he was performing solo or with a group, his music always resonated with fans. Here are ten of his best songs, ranked from number 10 to number one. Whether you’ve found an old favorite or you’re curious about something you’ve never heard before, go ahead and click on the YouTube link for each song. That way, you can hear what his sound was like for yourself, even if it’s for the very first time.

10. I Feel Like Hank Williams Tonight (1989)

 

Every country music fan knows that Hank Williams was one of the most revered, most loved individuals in the industry. Even today, decades after his death, he is still widely recognized as one of the people responsible for making country music what it is today. This is a song that talked about Hank Williams in both a professional and more personal sense, often paying homage to the singer and sometimes talking about the frailties that every human being has to face in one capacity or another.

9. Desperados Waiting for the Train (1973)

 

This is one of those songs that lends itself to the experiences of the person listening to it. As such, its meaning can be slightly altered depending on what the particular individual who is hearing the lyrics associates with it. As far as the lyrics themselves are concerned, it deals with people who have been traveling on the road together for so long that they almost feel like family in one capacity, yet in another capacity they feel restless, like they want something completely different from what they have. The train they’re waiting for isn’t necessarily a train in the literal sense as much as it is a figurative means of taking them away from everything that’s no longer suitable for them.

8. Railroad Lady (1977)

 

This is a typical country song of the 1970s. There’s not a lot of deep meaning to it, but instead only a song about a man meeting up with a woman with a somewhat checkered past. In the song, neither of them really care what type of past the other has, largely because they’re more concerned with the lust that they are feeling than anything else.

7. Sangria Wine (1973)

 

This song is about exactly what it says it is, wine. It talks about loving sangria wine and drinking as much of it as one possibly can. The song goes on to name all of the benefits of drinking so much wine, as well as having parties that include copious amounts of this particular form of alcohol.

6. Jaded Lover (1975)

 

This is one of those love gone wrong songs, the type that was wildly popular during the 1970s, especially on the country music front. In the song, a couple falls out of love and one of the people involved ends up watching the other one move from person to person in an attempt to find love, with virtually every relationship they are involved in ending in exactly the same manner. In the song, the person who is the jaded lover is standing by and watching all of this happen, knowing very well when the other individual falls in love, how it will eventually end and how they will ultimately make the other person feel.

5. Gettin’ By (1973)

 

Country music could be somewhat unique in the 1970s, and this is one of those songs that exemplifies that fact very well. At its core, it’s a song about making do with what you have and finding a way to make it work for you, even when it isn’t exactly what you want or even what you need. It’s important to remember that the 1970s were a time when people had a tendency to find a way to create contentment out of what they had as opposed to putting themselves into mountains of debt in order to achieve things that they couldn’t actually afford. This song is a bit tongue-in-cheek, but that is essentially the message that it is sending.

4. L.A. Freeway (1972)

 

This is a song about someone who never wanted a particular lifestyle, yet found themselves right in the middle of it because of the person they love. In this particular case, it involved them moving to Los Angeles and becoming part of the rat race when they would much rather be out in the middle of nowhere riding a horse down a dirt road. The song then goes on to talk about that person moving away from it all and going back to their roots because they simply can’t take it anymore. You might even go as far as saying that the song represents trying to become someone you’re not because that’s what you believe other people want you to be. More importantly, it’s about rediscovering who you really are and being true to those roots, even when it involves making changes that are painful in the moment.

3. Up Against the Wall Redneck Mother (1973)

 

This is a somewhat strange, yet interesting little song that talks about a person who can’t seem to stay out of trouble to save their soul. The song lyrics indicate that it isn’t really this person’s fault that he’s always in trouble or finding himself on the wrong side of things, largely because he was brought up that way. It directly pokes fun at the redneck stereotype that is so often associated with the state of Oklahoma, saying that if it weren’t for his redneck mother living in Oklahoma, he wouldn’t be in all the trouble that he’s in.

2. Pissin’ in the Wind (1975)

 

You’ve probably heard this phrase once or twice in your life. It refers to doing something that’s completely pointless. It can be used to indicate a person who is doing something useless, that they’re not really doing anything at all or that what they are doing amounts to nothing because they would get just as much done by beating their head against a brick wall. The song almost celebrates this lack of productivity, if you will. The lyrics talk about people not really achieving that much and then telling their grandchildren about their efforts (or lack thereof) with a smile.

1. Mr. Bojangles (1968)

 

This song probably sounds almost comical to someone who’s just hearing it for the first time in today’s world, but it’s actually rather sad. It is about a man who has spent the majority of his life traveling alone, getting drunk everywhere he goes and either dancing in public or in bars and other types of establishments for whatever money someone is willing to throw at him. Throughout his entire life, his only companion was a dog that traveled around with him. The song points out the fact that the dog has now been dead for twenty years and the man still cries every single day because it was the only friend he’d I ever known.

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