Top 10 Jerry Jeff Walker Songs

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Our Top 10 Jerry Jeff Walker Songs list presents the best Jerry Jeff Walker Songs like “Mr. Bojangles,” “L.A. Freeway,” “Jaded Lover” and more. New Yorker turned true blue Texan, Jerry Jeff Walker was originally born as Ronald Clyde Crosby on March 16, 1942. His upbringing served as an influence on the young man’s eventual career path in the mix of country and folk music. Prior to becoming a recording artist, the young Crosby first joined the National Guard after graduating from high school. He later became discharged so he could tour across the country as a musical performer. Before adopting the name of Jerry Jeff Walker as his official stage name, he began with Jerry Ferris. Eventually, he had it legally changed to Jerry Jeff Walker as of 1968.

Tried & True

The first part of Jerry Jeff Walker’s career started in the genre of folk music, co-founding Circus Maximus as a band with Bob Bruno. However, after two years and two studio albums, the difference in each artist’s musical interests saw Bruno venture into the direction of jazz while Walker further focused on folk. Starting in 1968, he began his solo career, starting with the recording and release of “Mr. Bojangles.” After settling in Austin, Texas, the influence of country music fused with Jerry Jeff Walker’s folk style, thanks to his association with Waylon Jennings and Willie Nelson. In fact, Walker’s name was mentioned in “Luckenbach, Texas (Back to the Basics of Love),” a collaborated performance by Jennings and Nelson that became a hit in 1977.

In 1986, after recording a series of albums for mainstream labels such as Elektra and MCA, Jerry Jeff Walker opted to go independent. Tried & True Music became his own label in 1986, managing this new entity with his wife as of 1974, Susan Streit. Year after year, there would be an annual celebration held in Gruene, Texas, that was timed on or near Walker’s birthday. This highly popular event brought in some of the biggest talents from the country and folk music as they’d perform music and tell tales.

Jerry Jeff Walker Legacy

In total, Jerry Jeff Walker recorded and released thirty-eight albums and thirteen singles. “Mr. Bojangles,” Walker’s signature hit song, was released twice. The first was the classic that became his breakthrough hit in 1968 while the second was a 1977 live version. He was known as the man who contributed one of the most important folk songs in American history, as well as the founding father of Texas country music as the fans know it. When he lost his three-year battle with throat cancer on October 23, 2020, the world of music was rocked by the loss of a legend.

From a talented songwriter with a knack for quality storytelling to one of the music industry’s most influential contributors, Walker has performed some of the best alternate versions of hit singles that were originally recorded by other artists. While artists like Jennings and Nelson had their names soar as top-rated country music stars, Jerry Jeff Walker’s remained somewhat obscure. However, “Mr. Bojangles” immortalized his name, not to mention see more than enough royalty money flow in. This allowed him to explore his creativity on his own terms instead of answering to commercialized expectations laid out by corporations. Laid-back and carefree, Jerry Jeff Walker was able to enjoy a star-quality lifestyle without having to contend with such a heavily publicized pricetag. This was perfect for Walker as it was never his intention to become so famous, to begin with.

Top 10 Jerry Jeff Walker Songs

#10 – Railroad Lady

“Railroad Lady was a song narrated by Jerry Jeff Walker as a man meeting with a woman with a checkered past. Despite whatever previous history the two had before they met, it wasn’t enough to stop them from at least sharing a bit of romance while they had the chance to do it. For Walker, this was a song he recorded in 1977 for the album, A Man Must Carry On. For good old classic country music with quality storytelling, Walker was a genius at his craft, even if he may not have been among the top stars constantly hitting the US Billboard charts like a regular. His laidback style was what made him a refreshing welcome among fans who cared more about quality music than trending hits.

#9 – Keep Texas Beautiful

In 1994, the final single released by Jerry Jeff Walker as a recording artist was “Keep Texas Beautiful.” Although it did not appear on any official music charts, it perfectly illustrated Walker’s love for a state that became his home and final resting place. Jerry Jeff Walker loved Texas and Texas loved him back.

#8 – The Pickup Truck Song

In 1989, “The Pickup Truck Song” became a number sixty-two hit on the US Billboard Hot Country Songs chart for Jerry Jeff Walker. From the album, Live at Gruene Hall, this classic song revolved around his grandfather’s old Chevy pickup truck that didn’t look like much and seemed to serve as a garbage dump for the man who owned it. When riding the truck, the memory inspired Walker to perform this what was a bittersweet song that had a bit of comedy to its history.

#7 – Trashy Women

“Trashy Women” was a single first covered by Jerry Jeff Walker in 1989 and it became a number sixty-three hit on the US Billboard Hot Country Songs chart. For Confederate Railroad, their coverage of this song became a number ten hit in 1993. For Walker, he first heard “Trashy Women” from its writer, Chris Wall. Inspired, he asked to be taught the lyrics so he could record it and release it as a single. The tale of a sophisticated man taking an interest in “Trashy Women’ became a big fan favorite, especially with the bit revolving around the man’s prom date and her Dolly Parton wig.

#6 – Jaded Lover

On the US Billboard Hot Country Songs chart, “Jaded Lover” became a number fifty-four hit for Jerry Jeff Walker after it was released as a single in 1975. It came from the album Ridin’ High, which was an MCA Records release. This is a classic love gone wrong song that illustrates just how talented Walker was as a musical storyteller. Although it didn’t top any official music charts, it was an immensely popular country music song the fans couldn’t get enough of. Nothing beats the twang of an acoustic guitar and the laid-back lyrical style of a man’s woes after realizing his special someone betrayed the love he had for her.

#5 – London Homesick Blues

Originally recorded and released in YEAR by Gary P. Nunn, Jerry Jeff Walker’s “London Homesick Blues” became the official theme song for Austin City Limits from 1977 until 2004. In 1973, songwriter Gary P. Nunn had this song written while he was staying with a friend in London, England. In the lyrics, Nunn made reference to the Armadillo World Headquarters, which was located in South Austin, Texas. It was a popular hangout for fans and performers of the counterculture that enjoyed its run for about a decade, spanning from 1970 until 1980.

#4 – Up Against the Wall Redneck Mother

“Up Against the Wall Redneck Mother” was a Ray Wylie Hubbard tune that was recorded in 1973 by Jerry Jeff Walker. Poking fun at the Oklahoma-based redneck stereotype, Walker performed a comedic narrative as a man constantly in trouble. The blame fell on the upbringing he experienced while raised by a redneck mother.

#3 – L.A. Freeway

Guy Clark’s “L.A. Freeway” was a hit single covered by Jerry Jeff Walker and became a number ninety-eight hit on the US Billboard Hot 100 and in Australia in 1972. This was the second hit in Walker’s career, taken from his self-titled album that was released by MCA Records. For Walker, “L.A. Freeway” was a song about a man stuck living in the rat-race lifestyle of a busy city he never really wanted. By the time the song is over, he has moved back to his roots, leaving the freeway of madness behind him so he could rediscover himself.

#2 – Desperados Waiting for a Train

Written by Guy Clark and recorded by Jerry Jeff Walker, “Desperados Waiting for a Train” was a 1973 classic from the album, Viva Terlingua. It also appeared as a cover song on albums belonging to a wide variety of artists as the appeal was just too great to ignore. This lyrical tale featured his grandmother’s boyfriend serving as a fatherly figure to Walker while he was growing up. While this may not have been a hit for Walker personally, it became a big hit for the Highwaymen when it peaked at number fifteen on the US Billboard Songs chart in 1985. According to the Western Writers of America, “Desperados Waiting for a Train” became one of the Top 100 Western songs of all time.

#1 – Mr. Bojangles

“Mr. Bojangles” became the signature hit single for Jerry Jeff Walker after it was released in 1968. The song revolved around an alcoholic tap-dancer Walker met in New Orleans while the two were in jail together. The song’s popularity peaked at number seventy-seven on the US Billboard Hot 100 and at number fifty-one on the RPM Canadian Country Tracks chart. It was even more popular in Australia, as it charted as high as number twenty-two there.

Since its release, it has been covered many times over by a variety of musical artists, including Nitty Gritty Dirt Band’s version that made it a number nine hit on the US Billboard Hot 100 in 1971. “Mr. Bojangles” is credited as one of the most influential songs of all time and it was believed the pseudo name originally came from the Bill “Bojangles” Robinson. Robinson was the top-earning African-American entertainer during the first half of the American entertainment industry.