Hank Williams' 1949 Hit 'I'm So Lonesome I Could Cry' Voted Best Classic Country Song
The icons of classic country music, like Waylon Jennings, Dolly Parton, Johnny Cash, Merle Haggard, Patsy Cline, Willie Nelson, and more, released a slew of legendary songs. Despite that, it turns out that a track recorded by another beloved figure surpassed all of their biggest hits. According to a country music fan vote, Hank Williams' 1949 track "I'm So Lonesome I Could Cry" stands above all the rest as the greatest classic country song.
Why Country Music Fans Named Hank Williams 'I'm So Lonesome I Could Cry' the 'Best Classic Country Song'
In October 2025, Ranker updated its article that allows fans to vote on the "best classic country songs." Of the 195 different songs that have received votes in the article, Hank Williams' "I'm So Lonesome I Could Cry" is ranked No. 1 with 1,092 upvotes. That said, the competition for the top spot is fierce as "Mammas Don't Let Your Babies Grow Up to Be Cowboys" from Waylon Jennings and Willie Nelson is No. 2 with 1,047 upvotes.
In addition to topping the Ranker list, Williams' song has earned other accolades. Most notably, Rolling Stone has named "I'm So Lonesome I Could Cry" the fourth greatest country song of all time and the second saddest country song ever.
Originally released in 1949, "I'm So Lonesome I Could Cry" was never meant to be a single. Instead, when Williams released "My Bucket's Got a Hole in It" as a single, it was the B-side. Back when singles were released as records, the main song would be called the A-side, and the accompanying song, which wasn't meant to be the main focus, was the B-side. In order to listen to the B-side, the record would have to be flipped.
Even though it wasn't planned to be spotlighted, "I'm So Lonesome I Could Cry" was such an emotionally raw song that listeners have connected to it for decades now. While all of the song's lyrics are impactful, a portion in the middle really stands out and has helped ensure the track has become an all-time classic.
Did you ever see a robin weep
When leaves began to die?
Like me, he's lost the will to live
I'm so lonesome I could cry
The silence of a falling star
Lights up a purple sky
And as I wonder where you are
I'm so lonesome I could cry
The Top 20: Ranker's "Best Classic Country Songs"
- No. 20: Willie Nelson - "Blue Eyes Crying in the Rain"
- No. 19: Dolly Parton - "I Will Always Love You"
- No. 18: Randy Travis - "Forever and Ever, Amen"
- No. 17: Waylon Jennings - "Luckenbach, Texas (Back to the Basics of Love)"
- No. 16: Marty Robbins - "El Paso"
- No. 15: Waylon Jennings - "Good-Hearted Woman"
- No. 14: Hank Williams - "Hey Good Lookin'"
- No. 13: Patsy Cline - "I Fall to Pieces"
- No. 12: Willie Nelson - "On the Road Again"
- No. 11: Willie Nelson - "Always on My Mind"
- No. 10: Johnny Cash - "Folsom Prison Blues"
- No. 9: Patsy Cline - "Crazy"
- No. 8: George Jones - "He Stopped Loving Her Today"
- No. 7: Merle Haggard - "Mama Tried"
- No. 6: Dolly Parton - "Jolene"
- No. 5: George Strait - "Amarillo by Morning"
- No. 4: John Denver - "Take Me Home Country Roads"
- No. 3: Hank Williams - "Your Cheatin' Heart"
- No. 2: Waylon Jennings & Willie Nelson - "Mammas Don't Let Your Babies Grow Up to Be Cowboys"
- No. 1: Hank Williams - "I'm So Lonesome I Could Cry"
Next: 1990 No. 1 Hit Ranked Best Country Song of All Time Still Holds Up Today
This story was originally published by Men's Journal on May 25, 2026, where it first appeared in the News section. Add Men's Journal as a Preferred Source by clicking here.
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This story was originally published May 25, 2026 at 12:51 PM.