Chart success isn’t always the same as quality. Countless songs across multiple genres never appeared on a Billboard chart or any other chart, for that matter. At the same time, there are plenty of nostalgic country classics that feel like pieces of my life that never reached the top of the chart.
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I think we all have those songs that we love but didn’t get the recognition they deserved for one reason or another. Some are hits but didn’t reach the top of the charts others are hidden gems that entirely escaped the notice of critics and failed to chart altogether. Here are a few of my favorite underappreciated tracks.
“Amarillo by Morning” by George Strait
It didn’t take George Strait long to find his stride. He notched 18 No. 1 singles between his debut track “Unwound” in 1981 and the end of the ‘80s. However, this single from his sophomore album Strait from the Heart wasn’t one of them. I know I can’t be alone in wondering how “Amarillo by Morning” only reached No. 4 nearly every time I hear it.
David Alan Coe once sang about “The perfect country and western song.” While “Amarillo by Morning” doesn’t say anything about getting drunk, mamas, trains, or prison it’s pretty close to perfect. The Western swing-influenced arrangement, the story about a heartbroken rodeo cowboy, and Strait’s vocal delivery make this one an all-timer for many country fans.
Beyond wondering why this wasn’t a bigger hit, it makes me nostalgic for the days when I’d help my mom—who is still a Strait superfan—clean the house while she cranked King George’s tunes and other classics on our home stereo.
“Midnight in Montgomery” by Alan Jackson
This is another ‘90s country classic that never made it to the top of the chart. Alan Jackson co-wrote it with Don Sampson and released it as the fourth single from his sophomore album Don’t Rock the Jukebox. How this song never went to No. 1 is beyond me.
“Midnight in Montgomery” is country gold. It’s a ghost story about meeting the spirit of Hank Williams at his grave on the anniversary of his death. The lyrics are also packed with references to Williams’ songs. It could have missed the Billboard country chart completely and it would still make me nostalgic for the good old days when country radio still played songs that sounded like country music.
“Mr. Bojangles” by Jerry Jeff Walker
Written and recorded by Outlaw Country legend Jerry Jeff Walker, “Mr. Bojangles” is a certified classic. However, when Walker released it as the sole single from his 1968 album of the same name, it failed to chart. The Nitty Gritty Dirt Band had more success with the song when they released it in 1970 as a single from Uncle Charlie & His Dog Teddy. Their rendition of the song reached No. 9 on the Billboard Hot 100 and failed to make the country chart.
No matter who is singing it, “Mr. Bojangles” is a beautiful song that tells a memorable story about the hardships of a traveling street performer. Hearing this song makes me nostalgic for the days when a good friend of mine was working hard to get me into country music. I’ll never forget hearing, “Dude, you HAVE to hear this,” before being introduced to this and countless other classics.
“L.A. Freeway” by Guy Clark
Jerry Jeff Walker was the first to record this country classic but it’s Guy Clark’s version that makes me nostalgic for long drives with the windows down, singing along at top volume. Clark wrote the song in 1970, shortly after moving from Los Angeles to Nashville, and recorded it for his 1975 debut album Old No. 1.
Clark didn’t release the song as a single and Walker’s rendition failed to chart. However, that doesn’t change the fact that this is a great song. It’s a phenomenal example of Clark’s ability to tell a personal story—even addressing his wife by name in the lyrics—and make it feel universal.
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