The Saddest Hank Williams Songs

Country artist Hank Williams was known for his numerous hit songs. Even if you’re not a fan of country music, chances are you know at least a few of his famous tunes. 

Williams lived a hard life, and he reflected that in his lyrics.

So we decided to learn more about the King of Country Music and the sad songs he made so famous.

Let’s jump in!

About Hank Williams

Hiram “Hank” Williams was born on September 17, 1923, in Mount Olive, Alabama. His dad, Elonzo, worked as a railroad engineer for a lumber company. His job required the family to relocate between various towns in southern Alabama. 

Hank started life with spina bifida, which would later play a part in his addiction to drugs and alcohol. In 1930, his father was diagnosed with a brain aneurysm and entered a Veteran’s hospital for long-term care. 

Hank’s mother, Lillie, raised him and his sister essentially as a single mother from then on. They moved several times, eventually settling in Montgomery, Alabama, where Lillie opened a boarding house. 

Hank got his first guitar at the age of 8. While living in Georgiana, Alabama, he met a blues street musician, Rufus “Tee Tot” Payne. Tee Tot gave young Hank guitar lessons in exchange for meals Hank’s mother prepared for him. Hank Williams would use the style learned from Payne in most of his later songs.

Until 1937, Williams went by his birth name of Hiram. But by the age of 14, he decided Hank suited him better for playing blues music. Around this same time, Hank caught the attention of local radio station producers from WFSA. He regularly played his guitar and sang on the street in front of their studio. 

After performing a few times on the radio, the producers gave Hank his own 15-minute show twice a week. This opportunity led to Hank earning enough money to start his band, The Drifting Cowboys. 

The Drifting Cowboys played shows throughout central and southern Alabama. They did so well that Hank dropped out of high school at age 16 to tour full-time.

Increasing Fame

His mom became their booking agent and even drove them to some of their gigs. They booked shows as far away as Georgia and the Florida Panhandle. Between tours, Williams returned to Montgomery to host his radio show.

With success came money, which Hank began to spend on alcohol, using it to deal with increasing back pain from ongoing spinal issues. 

World War II began in 1941 and proved to be the beginning of difficult times for Williams. While he wasn’t medically able to be drafted for military service, his bandmates were. 

Hank hired replacements, but his alcohol use drove most of them away. He even showed up to his radio show intoxicated, which led to his eventual firing in 1942. 

The war and alcoholism temporarily halted Hank’s role as a touring musician. So, he picked up a job with a shipbuilding company in Mobile, Alabama. There, he met aspiring musician Audrey Sheppard. They married in 1944 and moved to Montgomery, where Audrey helped Hank regain his radio show. 

Hank Williams wrote many new songs to perform on his WFSA radio program. With his popularity increasing, Audrey stepped in as Hank’s manager sometimes singing duets at some of his concerts. 

In 1946, Hank traveled to Nashville, Tennessee, to meet with music publisher Fred Rose. This led to Williams signing his first recording contract with MGM Records. 

Williams released his first hit song, Move It On Over, in April 1947. Soon after, he and Audrey moved to Shreveport, Louisiana, where Hank joined the Louisiana Hayride radio show. This introduced radio audiences across the Southeast to Hank Williams and his successful country songs. 

Hank and Audrey’s son, Randall Hank Williams (professionally known as Hank Williams Jr.), was born in May 1949. The following month, Hank made his Grand Ole Opry debut.

A Brilliant Legacy

The early 1950s proved to be the height of Hank Williams’ career. However, his increasing dependence on alcohol and drugs began to take its toll on his daily life and career. 

His already turbulent marriage to Audrey ended when they divorced in 1952. Soon after, The Grand Ole Opry fired him for regularly showing up to perform heavily intoxicated or not showing up at all.

Hank met and married his second wife, Billie Jean Jones, in October 1952. The remainder of that year, Hank Williams performed his last concerts, all while under the influence of alcohol and drugs. 

In the early morning hours of January 1, 1953, Hank died in the back seat of his Cadillac. He was 29 years old. He and his driver had been going from Knoxville, Tennessee, to a show in Canton, Ohio. 

Hank Williams left a legacy of hit songs and a style unlike any other musician at the time. He’s been credited as influencing artists like Elvis Presley, Bob Dylan, Johnny Cash, George Strait, and even The Rolling Stones. 

Hank Williams released 11 number one hit songs and numerous other Top 10 country tunes. Posthumously, his popularity continued to grow. The Songwriters Hall of Fame inducted Williams in 1961, and in 1987, he received a Grammy Lifetime Achievement Award. 

With the troubled life he led, it’s no wonder Hank Williams wrote some of the saddest songs in country music history. Let’s take a look at some of them. 

#7 Your Cheatin’ Heart 

About the Song: Hank Williams often wrote from personal experience. In this case, the divorce from his first wife, Audrey, inspired the lyrics. It’s pretty clear why that marriage ended.

Greatest Lyric:

Your cheatin' heart will pine someday
And crave the love you threw away
The time will come when you'll be blue
Your cheatin' heart will tell on you

First Appearance: MGM Records released this song in January 1953, shortly after Williams’ death.

#6 Moanin’ the Blues

About the Song: There’s no chance a song with this title is anything but sad. Williams seems to confess in these lyrics that he didn’t always treat his lady right. 

You can hear Hank Williams playing the drums in this number. Only one other song he wrote, Kaw-Liga, features him on drums.

Greatest Lyric:

If you want a good girl to stay around
You gotta treat her nice and kind
If you do her wrong, she'll leave this town
And you'll almost lose your mind
Then you'll be moanin', moanin' the blues

First Appearance: Released in October 1950, Moanin’ the Blues became Williams’ fourth number-one hit song.

#5 Cold, Cold Heart

About the Song: This blues ballad is full of sadness and heartbreak. Hank sings about dealing with his lover’s pain from a former relationship. 

There’s some controversy surrounding the origins of this Hank Williams song. Paul Gilley, a young songwriter from Kentucky, may have written the words. Rumor has it that Williams paid Gilley for the rights to the tune and allowed Hank to take credit for it. 

Greatest Lyric:

Another love before my time 
Made your heart sad and blue
And so my heart is paying now 
For things I didn't do

First Appearance: Recorded in Nashville in December 1950, MGM Records released the single two months later in February 1951. 

#4 Lost Highway

About the Song: While Hank wrote most of his songs, this one is an exception. Written by blind country singer Leon Payne, Lost Highway depicts someone feeling hopeless after “a life of sin.”

As the story goes, Payne wrote the lyrics while hitchhiking from California to Texas to visit his sick mother. He sat on the side of the highway, waiting for his next ride, while the words came to him. 

Greatest Lyric:

I'm a rollin' stone, all alone and lost
For a life of sin, I have paid the cost
When I pass by, all the people say
Just another guy on the lost highway

First Appearance: Bullet Records released Payne’s single in October 1948.

#3 Alone and Forsaken

About the Song: The song begins with colorful imagery and ends with bleak despair. Hank Williams wrote and recorded this folksy ballad in 1948. 

The recording released is from a radio performance on the Shreveport, Louisiana station KWKH. 

Greatest Lyric:

We met in the springtime when blossoms unfold
The pastures were green and the meadows were gold
Our love was in flower as summer grew on
Her love like the leaves now have withered and gone

First Appearance: The date of the radio show that Hank Williams performed this song is unclear. Records indicate it happened sometime between August 1948 and May 1949. 

#2 Lovesick Blues

About the Song: While not a Hank Williams original, his recording made the song a popular country hit. In fact, it’s considered Hank’s signature song and one he’d end his shows with regularly. He was even given the stage nickname “Mr. Lovesick Blues” and “The Lovesick Blues Boy.”

Greatest Lyric:

Such a beautiful dream
I hate to think it's all over
I've lost my heart it seems
I've grown so used to you somehow

First Appearance: Lovesick Blues first appeared in the 1922 Tin Pan Alley musical Oh! Ernest. 

#1 I’m So Lonesome I Could Cry

About the Song: Williams’ first wife, Audrey, inspired these sad lyrics. Initially, Hank wanted this song to be a spoken-word piece, but fellow musicians convinced him to set it to music. 

Over 300 versions of this song exist. Elvis Presley, who recorded a live performance in 1973, called it “the saddest song I’ve ever heard.”

Greatest Lyric:

I've never seen a night so long
When time goes crawling by
The moon just went behind the clouds
To hide its face and cry

First Appearance: MGM Records released this song in November 1949. It appeared as the B-side to the more uptempo tune My Bucket’s Got a Hole in It.

Reflections of Hank

So there you have it—seven of Hank Williams’ saddest songs sure to bring a tear to most eyes. People say good country songs reflect life’s toughest moments. These tunes certainly seem to do just that!

Which are your favorite of Hank’s saddest songs?