Jerry Jeff Walker’s Hit Songs [Here’s A List]

Jerry Jeff Walker’s most popular songs include “Mr. Bojangles,” “Jaded Lover,” “Up Against The Wall,” “Redneck Mother,” “Pissin’ In The Wind,” “LA Freeway,” “Trashy Women,” and “Desperados Waiting For The Train.”

Jerry Jeff Walker, born on March 16, 1942, was an accomplished American country and folk singer as well as a songwriter. He delighted his fans with chart-topping songs that resonated well with listeners and one of his most famous songs is “ Mr. Bojangles,” which brought him widespread recognition.

His musical talent extended beyond the country genre, as he excelled in subgenres like outlaw country and progressive country.

Jerry Jeff Walker received recognition for his contributions, earning various awards, including MCA awards, and also received Grammy nominations for his outstanding work in the music industry.

Studio Albums	38 studio albums.
Compilation Albums	18 compilation albums.
Singles	13 singles.

What Stood as Jerry Jeff Walker’s Biggest Hits?

If you’re searching for Jerry Jeff Walker’s greatest hits, you’ve come to the right spot. Continue reading to discover and enjoy these musical masterpieces.

Mr. Bojangles

Jerry Jeff Walker released the song in 1970 as part of the album “Mr. Bojangles,” and it instantly made its mark on the charts. The song beautifully narrates the poignant story of a man named Mr. Bojangles, a street dancer with a sad past.

Inspiration for the song struck Walker when he found himself in jail for public intoxication and encountered a fellow inmate who went by the name Mr. Bojangles. The lyrics paint a vivid picture of Mr. Bojangles’ life, dressed in worn-out clothes and shoes, dancing on the streets of the South, in minstrel shows, and at county fairs to entertain people.

The narrative takes a heartwarming turn as Mr. Bojangles shares his life story with the narrator. He reminisces about traveling with his dog, whose death left a huge mark on him, leading to two decades of grief. Despite this, Mr. Bojangles uses dance as a coping mechanism, performing on every available occasion in exchange for tips and drinks.

The song touches on the sorrowful aspects of Mr. Bojangles’ life, including his frequent encounters with the law due to his drinking habit. Nevertheless, the resilience of Mr. Bojangles shines through as he persists in dancing despite enduring life’s challenges.

Up Against The Wall Redneck Mother

As part of the “Night After Night” album released in 1995, this song quickly became a favorite among listeners. It cleverly addresses typical redneck culture with humor, managing to critique without being disrespectful.

The lyrics tell the story of a redneck born in Oklahoma, married, and living a life filled with drinking, driving pickup trucks, and having a gun rack – all symbols of redneck culture. The song playfully highlights how these symbols represent the stereotypical redneck lifestyle, including the troubles they might cause for others.

However, it takes a critical turn by pointing out that the redneck’s behavior is influenced by his mother, who believes she has done an excellent job raising him. The song implies that, despite her pride, the redneck’s actions may not be suitable for everyone.

Interestingly, the song even spells out the word “ mother,” associating each letter with symbols of typical redneck culture.

Pissin’ In The Wind

Featured in the album “Ridin’ High” in 1975, this song quickly became a hit, gaining widespread popularity. The lyrics delve into the theme of repeatedly making mistakes without learning from them until the realization dawns that the solution was surprisingly simple.

The song narrates how the protagonist and their friends persist in making the same errors, leading them into a cycle where the consequences not only affect them but also those around them. They humorously liken their nonchalant attitude and ongoing struggles to “ pissin’ in the wind,” acknowledging that such behavior can dirty and impact others.

Despite their struggles and regrets, they find ways to laugh it off. However, the turning point comes when they finally recognize their mistakes and realize that the solution to their problem is as straightforward as, well, just “ pissin’ in a sink.”

Trashy Women

Released in 1989, this song quickly became a hit, resonating with many hearts. The inspiration behind it stems from Walker’s admiration for women who don’t conform to societal expectations. The song tells the story of a protagonist raised in a sophisticated environment by parents who were taken aback as he embraced different interests and preferences over time.

As the protagonist grew older, his choices surprised his parents, especially when he took an older girl with a Dolly Parton wig to prom. This unexpected turn was a departure from what his parents had envisioned for him.

The song celebrates the protagonist’s love for music and wild girls, with “ trashy women” referring to those who defy societal norms – wearing tight clothing, dyed hair, and too much makeup.

Overall, the song encourages embracing one’s personality and uniqueness without feeling the need to conform to societal norms. It sends a positive message about leaving stereotypes in the past and being true to oneself.

Jaded Lover

Released in 1975 as part of the “Ridin’ High” album, this song has deeply connected with listeners. The lyrics revolve around a jaded lover, someone who lacks real interest in long-term relationships and isn’t eager to pursue them, often just passing time with people.

The protagonist becomes involved with this jaded lover and discovers a pattern – quickly moving on to someone new. This behavior stems from experiencing numerous failed relationships, leading the jaded lover to no longer seek anything beyond casual flings.

The song resonates with individuals who have felt let down in love by past relationships, and as a result, they may relate to the emotions of a jaded lover .

L.A Freeway

As part of the self-titled album, this song was released in 1972 and quickly gained immense popularity, striking a chord with many listeners. The inspiration behind the song came when the writer, Guy Clark , relocated from California to Nashville. The recording took place after Jerry Jeff Walker moved from New York to Austin.

The song beautifully captures the essence of moving to a new place, establishing a home, and the inherent risks involved. It reflects the emotional journey of individuals who choose to relocate for the better, even though the process of packing up memories and belongings can be overwhelming.

The narrative specifically touches on the experience of moving from a small town to Los Angeles for improvement. The reference to the risks on the LA freeway symbolizes the significant challenges and uncertainties the protagonist might face in undertaking this journey.

Desperados Waiting For The Train 

Released in 1973 as part of the “Viva Terlingua” album, this song stands out as a hit that deeply resonated with listeners. The song lies in exploring the theme of friendship and the emotional journey of facing loss.

The storyline revolves around two individuals in an unusual setting – one younger, the other an old man – sharing a remarkably strong bond. For the protagonist, the old man is more than just a friend; he serves as a mentor and even a father figure.

The friendship involves various shared experiences, from learning how to drive to stories narrated at the bar alongside the old man’s other friends. As the protagonist witnesses the old man getting older, it becomes challenging to accept reality, because the old man is seen as a hero. The emotional climax arrives when the old man passes away, leaving a void in the protagonist’s heart.

Ultimately, the song beautifully captures the strength of love and friendship between two individuals, transcending age and circumstances.

Final Thoughts

• Jerry Jeff Walker was an American country and folk singer known for his chart-topping songs.
• One of his most famous songs is “ Mr. Bojangles,” which brought him widespread recognition.
• Some other top hits include well-loved classics such as “Up Against the Wall Redneck Mother,” “Pissin’ in the Wind,” “Jaded Lover,” “Trashy Women,”and more.

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