16. “Wichita Lineman” (1968) is the second song on this list written by Jimmy Webb (By the Time I Get to Phoenix). Much of the credit goes to the strength of the Glen Campbell recordings. This should tell you a lot about the talent of these two individuals. After the success of Campbell’s cover of “By the Time I Get to Phoenix” in 1967 he wanted Webb to write him a similar song, one with the same type of time and place reference. A simple enough task if you are as talented as Jimmy Webb, so based on a drive he took through rural Oklahoma where he saw the solitary workers on utility poles he created this amazing and evocative story. It was missing just a couple things when he sent it to Campbell who then worked his guitar magic, plus some creative contributions from his producer/arranger Al De Lory. Throw in some more great guitar from fellow Wrecking Crew member Carol Kaye and you end up with this remarkable song. In 1968 it charted #1 on the Country chart and US Adult Contemporary in the US, #1 on two charts in Canada as well. It hit #3 on the Billboard Hot 100.

The song won Record of the Year at the Grammys in 1968 and Campbell won Best Contemporary-Pop Vocal Performance, Male. I find it a bit odd the song didn’t win at the Country Music Association Awards or Academy of Country Music awards but Campbell did win Male Vocalist at both and shared Best Album for Bobbie Gentry and Glen Campbell at the latter. I really should get around to dedicating a post to Jimmy Webb, he has had at least 10 songs hit the Billboard Top 10 charts. There are at least 301 versions of this song.

17. “Folsom Prison Blues” (1955) is a song written and performed by Johnny Cash. He is another with two songs on the Top 20 list. However, Johnny can’t take full credit for the creation of this now legendary song. He borrows heavily in fact from a song in “The Conductor” on the album Seven Dreams written by Gordon Jenkins. The train themed album contains a song within a song titled “Crescent City Blues” and sung by Jenkins wife, Beverly Mahr. If you give it a listen it draws a bit of a shocking comparison. In turn the melody of the song was taken by Jenkins from an instrumental song, coincidentally titled “Crescent City Blues” written in the 1930’s by the New Orleans/Chicago Blues artist known as Little Brother Montgomery. Cash heard Beverly Mahr on a record while in Germany when he was with the US Air Force, this was in 1951, before he became a recording artist. Cash had wanted Jenkins acknowledged on the song credits for the 1955 song but was assured by Sam Phillips there were no issues. Jenkins would later sue and Johnny paid him $75.000 dollars, presumably in Cash.

Regardless of the journey it is one special performance by Johnny Cash and one of the greatest songs in Music. Most well known for the live recording from Folsom Prison, and the album At Folsom from 1968. The original charted #4 in 1956 on the Billboard Country chart, as well as #4 and #5 on the the Pop charts. The live version hit #1 in both Canada and the US on the Country Chart. The song, including instrumentals and vocals in six languages has 300 versions.

18. “Wabash Cannonball” here we have another train song and the journey is no less circuitous in nature. It has been traced back to story’s of train riding hobos in the mid 1800’s. In 1882 J.A. Rolf published a song named “The Great Rock Island Route!!”. Then in 1904 William Kindt published an instrumental song “Wabash Cannonball” using the same melody and we don’t really know who wrote the revised lyrics. This has strong roots as an American Folk song and as many were, it was adopted by the Country genre. A.P. Carter of the legendary family had registered the song as his own when they recorded it 1932, but he did not write it. Before the Carter Family recorded the song it was first done by a popular Country Singer and Radio Host, Hugh Cross in 1929. The third time’s the charm as is often said so when Roy Acuff and His Crazy Tennesseans (vocals by Sam “Dynamite” Hatcher) released it in 1938 it became one of the biggest selling records of all time reaching the 10 million copies mark. You can hear many live performances where Roy Acuff himself is singing but to the best of my knowledge he never recorded the song in his own voice. Roy Acuff Jr. released a version in 1965.

To say that everybody in Country Music has done this song, which including adaptations now has 283 documented versions, is not overstating things. I mean there are five Hanks alone, Williams Jr. , Snow, Thompson, Lochlin and Smith! We also have Johnny Cash, Dolly Parton and Bill Monroe, even The Secret Sisters did it in 2010 but don’t tell anyone you heard it from me. Folk legend Pete Seeger did it, Woody Guthrie adapted the tune for his song “Grand Coulee Dam” as did Chuck Berry for “Promised Land”. Not surprising that a song about trains is so well traveled. Stay with me folks I have more puns in the caboose!

19. “Oh Lonesome Me” was written by Don Gibson, yet another name to appear twice in the Top 20 as his “I Can’t Stop Loving You” placed #5. Both songs were released at the same time (December 1957) and “Oh Lonesome Me” was the ‘A’ side of the single and “I Can’t Stop Loving You” the ‘B’ side. with backing vocals by The Jordanaires. However it was the ‘A’ side that hit #1 on the Country Chart and #7 on the Pop chart. Ray Charles as he did with “I Can’t Stop Loving You” would record “Oh Lonesome Me” and another Gibson song “Don’t Tell Me Your Troubles”. The Kentucky Headhunters would hit #8 on the Hot 100 Country chart with “Oh Lonesome Me”.

If you look up unrequited love in the dictionary you would find this forlorn tune that is a Country Standard and another song that has been covered by just about everyone in Country Music, George Jones, Johnny Cash, Eddy Arnold, Kitty Wells, Loretta Lynn, Crystal Gayle, Anne Murray and Tanya Tucker to name just a few. Outside of Country there are renditions by Paul Anka, Sammy Davis Jr., Bing Crosby and Connie Stevens. Currently there are 281 versions of this song.

20. “Me and Bobby McGee” was written by Kris Kristofferson with a credit given to Fred Foster as his suggestion led to the writing of the song. Kristofferson is another person to have two songs on this list. The first of many Country chart appearances was the 1969 original by Roger Miller, reaching #3 in Canada and #12 in the US, Gordon Lightfoot hit #1 in Canada and #7 on the Pop chart and Jerry Lee Lewis with his 1971 release charted #1 and #40 on the Hot 100. There are currently 279 versions of this song, including Kristofferson himself in 1970, one of thirteen to be released that year. So it was a popular song. If you think that sounds like a lot there were 27 versions released in 1971. While most covers of the song are done in the County style or maybe a little more on the Folk side. The most memorable rendition of the song was the first of that stream of covers in 1971, and it was neither Country or Folk.

Janis Joplin recorded “Me and Bobby McGee” during the sessions for the 10 track album that was later named Pearl, which was her nickname. Janis would die from a drug overdose just three days after these recordings, October 4, 1970. The album and the single of this song were released in January of 1971. Both the song and the album would hit #1 on Billboard, it was her only top 40 song. The memorable and original song “Mercedes Benz” was also on the album but it did not chart. If you have heard the song you know that what she did with it was exceptional. It’s done with a breath of Country and quickly steps into an uptempo Blues song. If you have not listened you are missing out, click that link!

That’s the list, it was quite remarkable that so many names appear more than once. Hank Williams, Jimmy Webb, Glen Campbell, Don Gibson, Johnny Cash and once as a writer and once as a key performer we have Willie Nelson. However it is quite the contrast to the list for Pop Songs, where The Beatles dominate.

What is glaringly missing from both of these lists (Pop and Country) with 20 songs combined are ones written and or originally recorded by Women. I have to acknowledge Hedy West and her song “500 Miles’ that contributed to getting “I’m Nine Hundred Miles From Home” to #7. However, in order to feature more of those amazing songs from women I have to work quite a ways down the lists. The first I came across for Country artists was (not surprisingly) Dolly Parton with a song covered 249 times, which by any standard is an impressive number.

I’m working on a post that will feature the most covered songs either written and or originally recorded by women. Here is a teaser from that post and the obvious answer as to which Dolly Parton song tops the list.

“I Will Always Love You” was written by Parton and released as a single in March of 1974, as most will know it hit #1 on the Country Chart that year and a re-recording hit #1 again in 1982. In 1995 her duet with Vince Gill charted at #15. To my knowledge no other song has achieved this before or since. If that was not enough there are likely very few people on the planet over 35 years of age that don’t know Whitney Houston’s 1992 version for the movie The Bodyguard. It was a worldwide smash #1 hit song making it the only song to hit #1 on a Billboard chart three separate times. Whitney’s version became one of the few songs to re-enter the top 10 on the Billboard Hot 100 as after her passing in 2012 the song would peak at #3. This makes the song the only one to have not only the three #1 Billboard appearances but if you add her #53 showing on the Hot 100 for her 1982 version that is a total of six chart appearances, three on the Country and two on the Pop chart.

Note (March 29, 2024): I have received a comment that was quite adamant that “I’ll Fly Away” was the most covered Country Song of all time. If there is an oversight on my part I appreciate comments that address that, in a positive manner mind you. When that happens I make the changes after I do my usual back checking. In this case, I believe I have my facts straight, but I thought I’d explain this one anyway. It may provide some insight as to the process involved in compiling my lists.

True, “I’ll Fly Away” has certainly been covered by many Country and Bluegrass artists over the years.

First, the number of documented actual Country versions appears to be less than 200 and that does not put it in the top 20 according to the numbers I found on Secondhandsongs.com. “Me and Bobby McGee” at #20 at the time I first posted had 279 versions. Secondly, I can’t find another source to quote any different much less accurate statistics.

More importantly, the song does not qualify for my list to begin with, as it originated as a Gospel song, not a Country song. Much the same way as “Amazing Grace”, there are many Country singers covering the song but that does not make it a Country Song. “I’ll Fly Away” was written by Albert E. Brumley in 1929, he was a pioneer in Southern Gospel compositions. It has been performed by Church Choirs and sung as a hymn many times since first published in 1932. In the form of a sermon (with Choir) by Rev. J.M. Gates a live recording was released on Feb. 7, 1940. “I’ll Fly Away” was first covered in a song format by a ‘Country’ artist (The Chuck Wagon Gang) in 1949. Should I do a list of Country Gospel Songs/Covers it may very well be on that list.