I recorded Hank Williams’s “You Win Again” as part of my Quarantine Sessions project with regular co-collaborator instrumentalist, Mark Caserta, and singer Kathryn Lewis. You can listen to our full cover at Soundcloud. In this post, I will offer some thoughts on the life of the legendary Hank Williams.

You can catch Kathryn and me on Live Muzic Mondayz every Monday night from 8:00 P.M. to 10:00 P.M. – videos stream on the official Facebook page.

My Introduction to You Win Again

I first heard the Ray Charles version of You Win Again from his iconic 1962 album, Modern Sounds in Country and Western Music, which I discussed in my previous Quarantine Sessions post. You Win Again was originally written and recorded by Hank Williams in 1952. The Charles version led me to Williams’ original, with which I am now well-acquainted. Having an interest in Williams’ music and work, I decided to do some research into his life and background.

Separating Hank Williams Fact and Fiction

Sketch of Hank Williams by Victor V. Gurbo.
Sketch of Hank Williams by Victor V. Gurbo.

Hank Williams is one of the most influential figures in American music. His look, sound, and songs are part of American culture and have been copied time and time again. Williams’ songs have been covered by luminaries such as Johnny Cash, George Jones, Chuck Berry, and The Rolling Stones. Williams’ most famous song, Your Cheatin’ Heart, is a part of the cultural lexicon.

Hank Williams accomplished a great deal in a short time. He died at the age of 29 in 1953. As is the case with many famous artists – especially those who lived short lives – there are many legends about Williams. It is often difficult to separate fact from fiction.

I had once been under the impression that Williams grew up in a brothel. As the story went, his experience growing up in a brothel inspired his material. However, I later learned from a documentary that this was not the case. Williams read the equivalent of Cosmo magazine and drew inspiration from it to write compelling pop songs.

I was privy to other Williams legends. He supposedly used cheap guitars because he needed them to fend off the husbands of women who were swooning over him while he was on stage. Supposedly, Williams was banned from the Grand Ole Opry for drunken behavior. How did he die? The account I heard was that he died in the back of a Cadillac on the way to a New Years Eve show. Are any of these stories true?

The Life and Times of Hank Williams

Hank Williams, named Hiram Williams, was born on September 17, 1923, in Butler County, Alabama. His parents were devoted Freemasons, which informed their decision to name him Hiram.


Williams was not a healthy child. He was born with Spina Bifida Occulta, a birth defect that affects the spinal cord. As a result, Williams suffered from debilitating back pain – which played a role in his later struggles with drugs and alcohol.

Williams’ father was a veteran of World War I. On account of injuries he suffered in that war, he spent the majority of Williams’s life in a veterans hospital. Williams’ mother was the sole guardian of Williams and his siblings and the provider for the family. She worked multiple jobs and opened a boarding house in order to earn enough. The story that Williams grew up in a brothel came from a family friend, who claimed that Williams told him that men were led to the upper floors of the boarding house during his childhood.

Learning Guitar

It is unclear when Williams received his first guitar. We do know, however, that he learned to play guitar from Rufus “Tee-Tot” Payne, an African-American blues street performer. Payne taught Williams in return for money and meals. Later in life, Williams would state that Payne was his only guitar teacher. He recorded one of Payne’s songs – My Bucket Has a Hole in It.

Although Williams was a brilliant songwriter, he never learned how to read or write music.

Becoming Hank Williams

According to anecdotes from people who heard him on stage, Hank Williams began going by “Hank” so his name would sound like a cat’s yowling. The effect was produced with his iconic western yowl.

Beginning His Professional Career

Hank Williams won a music contest in 1937. This achievement brought him to the attention of recording labels. Having found his path in life, Williams dropped out of school in 1939 to devote his life to music. He formed The Drifting Cowboys, and his mother acted as his manager.

Achieving Prominence

Most of the members of Williams’s Drifting Cowboys were drafted in 1941. Having lost most of his band to military service, his alcoholism worsened. Williams was forced to take other jobs while playing evenings in bars to get by. During this period, he met another singer by the name of Audrey Sheppard. They wed in 1944.

Shepard took over managing Williams’ career after their marriage. Over the coming years, Williams recorded some of his most well-known songs. He was accepted into the Grand Old Opry.

Subsequent Struggles

Williams was injured during a hunting trip in 1951. This injury exacerbated his preexisting back problems. He dramatically increased his drug and alcohol consumption, leading to his 1952 dismissal from the Grand Old Opry for “habitual drunkenness.”

Recording You Win Again

Williams and his wife divorced in 1952. One day later, he recorded You Win Again. However, according to Fred Rose, the producer, Williams had actually presented him with I Lose Again. Rose convinced Williams to change the name of the song to You Win Again.

Final Years and Death

Williams’ health declined in his final years, but he did not stop performing. His final single was I’ll Never Get Out Of This World Alive.

Williams had been scheduled to perform at the Municipal Auditorium in Charleston, West Virginia, on January 1, 1953. He was set to depart from Nashville, Tennessee. Due to an ice storm in the area, Williams hired a college student to drive him to the show. En route, Williams began to feel unwell, due in part to drugs and alcohol, and his hired driver convinced him to stop and see a doctor on the way. The doctor administered a shot of vitamin B-12, which also contained morphine, and caused a further negative reaction. Either during the night of December 31, 1952, or the morning of January 1, 1953, Williams passed away in the back of the Cadillac on the way to the show in West Virginia.

Those who had hoped to see Williams perform on New Years thought that the announcement of his death was a joke. They only realized that the announcement was quite serious when Williams’ band began playing his hit song, I Saw The Light.

Hank Williams was interred in Montgomery, Alabama, after what had been the largest attended funeral in Alabama history.

Much Truth to the Legends of Hank Williams

As it turned out, much of what I had heard about Hank Williams was true. But despite his short and often difficult life, or perhaps in part because of it, he was able to produce material that has stood the test of time.

Additional Thoughts on You Win Again

You Win Again has a different tone than many of Williams’s earlier songs. It has a darker, sadder, and more serious feel than much of Williams’s earlier content. It is certainly sadder than most of the songs I have covered as part of the Quarantine Sessions – as you will find in our cover.