#2. Your Cheatin’ Heart 

If I had one song to best display Hank Williams – in both sound and style, the song I would use is Your Cheatin’ Heart. Not for the first time on this list, it is a song about lost love, with infidelity occurring to the heartbreak of the narrator. 

One of the most iconic country songs of all time was created about ex-fiancé (surprise, surprise(!)) Audrey Williams with the lyrics quickly dictated to his now-wife while Hank drove. 

Hank’s bitterness is communicated with the song’s cheating heart a snide reference to Audrey, whose conscience will come back one day to hurt her. Her guilty feelings will soon come back to seemingly repossess her.  

The song was recorded in a single take, the only time Hank would perform the song, a tune backed by an all-star cast of session musicians. Although never seeing its full impact, Williams – according to the eponymously-named autobiography of this song – called the song “the best heart song (he) ever wrote.” 

Each line is topped off with the telling line “Your cheatin’ heart will tell on you.”  

The song saw a new life when Hank died within a few months of the single. It topped the Country Billboard charts for six weeks, selling over one million units. It has since been ranked within the upper half of Rolling Stone’s 500 Greatest Songs Of All Time. 

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#1. Lost Highway 

Those of you familiar with my work will know that – due to my ardent atheism – I find a lot of Hank’s religious works such as I Saw The Light and House Of Gold harder to appreciate (as good as they are) but even I can truly appreciate the greatness of Lost Highway. The best work of Hank Williams. 

This song’s influence has served the subsequent music scene greatly. Although Hank did not write this particular track, he helped popularise it to a wider audience. 

The opening line: “I’m a rolling stone, all alone and lost”, deriving from Biblical times, has served as inspiration for Bob Dylan’s Like A Rolling Stone and later the naming of The Rolling Stones. It has become a standard and classic work of Williams as many people’s favourite work, showing how effectively Williams crafted and adapted Lost Highway. 

The song, as expected, sings about life’s vices including drinking, gambling, and unfaithfulness, having “paid the price” for his life’s deviances. 

The narrator is painted as a once-successful, or at least once-sufficient, man whose sinful ways have led to a hopeless, directionless life. Now seemingly destitute and on the “lost highway”, Williams encapsulates feelings of disillusion, fear, and sorrowful anticipation. 

One of Hank’s strengths is constructing evocative and impactful closing lines 0 and this is no different: “Take my advice or you’ll curse the day, you started rollin’ down that lost highway.”  

The song may have best been summed up by The Guardian who put it thus: “an everyman doomed by luckless love to roam, rootless and alone, in constant search of redemptive purpose. Williams’ struggle to reconcile the sacred and the profane certainly helped him…but it’s his voice – cracked, careworn but never tired – that makes this the definitive reading of an all-time classic, and a high point in a career that had more than its share.” 

It is for all of this that Lost Highway is my pick for the greatest work of Hank Williams. 

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Hank Williams: The Hillbilly Shakespeare 

What more is there to say that shows the innovation and creation of country’s true megastar Hank Williams? 

Williams helped not only with the creation of new genres such as rock’n’roll but set the standard for country music including through his smorgasbord of themes presented in a simple yet compelling and emotive style. His description upon winning a 2010 Pulitzer Prize described him as having “craftsmanship as a songwriter who expressed universal feelings with poignant simplicity and played a pivotal role in transforming country music into a major musical and cultural force in American life.” 

When talking of post-war heroes, Hank has to be top of the musical hierarchy for that era, spreading country music to a wider commercial audience whilst also staying true to country music. 

Although Hank saw some success in his lifetime, it is incredibly sad and, considering his song’s subject matter, ironic that Williams died without being able to see how his legacy would only further blossom in the coming decades. 

Hank himself once humbly proclaimed: “I think I’m good enough to play and sing.” Yes, indeed you are Hank. Love live the Albama cowboy!