When Frank Sinatra’s smooth, swaggering voice belts out the lyrics to “Chicago (That Toddling Town),” he isn’t just singing about a destination; he is capturing the rebellious spirit of the “Roaring Twenties.” Among the vibrant descriptions of the city’s nightlife and excess lies a peculiar line that often piques the curiosity of modern listeners:
“The town that Billy Sunday couldn’t shut down…”
For many fans of Oldies music, this name might ring a bell from history books or religious revivals, but his presence in one of the most famous jazz standards of all time is no accident. To understand why a fundamentalist preacher is immortalized in a Sinatra classic, we must travel back to an era of Prohibition, moral crusades, and the cultural tug-of-war that shaped the American identity.
Who Was Billy Sunday?
Long before the mega-churches of today, Billy Sunday was the original superstar of the American evangelical movement. His journey to fame was as uniquely American as the music he eventually inspired.
From the Baseball Diamond to the Pulpit
In the 1880s, Sunday was a popular professional baseball player for the Chicago White Stockings (now the Cubs). However, after a religious conversion at the Pacific Garden Mission in Chicago, he traded his glove for a Bible. He began his religious career at the YMCA and slowly climbed the “kerosene circuit”—preaching in small, rural towns without electricity—before moving to major urban centers.
A Master of Performance
Sunday was not a typical solemn preacher. Influenced by his athletic background, his sermons were highly physical and animated. He was known to:
- Sprint across the stage to “slide home” for Jesus.
- Punch the air as if boxing with the devil.
- Walk an estimated mile within the confines of a single sermon.
His charisma and “rags-to-riches” story resonated deeply with Midwesterners, turning his revival meetings into massive public spectacles.
The Crusade Against “Wet” Chicago
While Sunday preached on many topics, from communism to evolution, his primary enemy was alcohol. He viewed the saloon as a “source of misery and crime,” and he became a leading figure in the Temperance Movement.
In the spring of 1918, Sunday returned to the city where his baseball career began to lead what he called a “crusade.” He built a massive tabernacle on Chicago Avenue, near Lake Michigan, capable of holding 16,000 people. Despite his popularity and the fact that Prohibition became law shortly after, Sunday faced an uphill battle in Chicago.
The city was the heart of the “wet” resistance. Even as Sunday filled his tabernacle with thousands of followers, the streets were becoming the playground of mobsters, bootleggers, and underground jazz clubs. The moral regulation Sunday fought for was constantly undermined by the city’s thirst for freedom and entertainment.
Why Sinatra Sang About Him
The song “Chicago” was written in 1922 by Fred Fisher, right in the middle of the Prohibition era. It was intended to celebrate the city’s refusal to be tamed by moral reformers. However, it didn’t become a global sensation until Frank Sinatra recorded it in 1957 for the film The Joker Is Wild.
The Clash of Values
Sinatra, the ultimate icon of cosmopolitan cool, was the polar opposite of Billy Sunday. Sinatra valued the nightlife, the cocktails, and the “excess” that Sunday spent his life trying to eradicate.
By singing the line “The town that Billy Sunday couldn’t shut down,” Sinatra was taking a victory lap on behalf of the city. It was a nod to the fact that, despite the best efforts of the most powerful preacher in America, the spirit of Chicago—its music, its grit, and its nightlife—remained untouchable.
The Bittersweet Legacy of an Era
Today, Billy Sunday’s name survives largely through this mid-century anthem. For many, it is a bittersweet legacy. A man who moved millions with his voice is now remembered as the antagonist in a song celebrating the very things he hated.
Yet, this intersection of religion, law, and music provides a fascinating window into the golden era of American music. It reminds us that behind every classic “oldie” is a story of a changing nation. The song “Chicago” remains a testament to a city that was too big, too loud, and too vibrant to be silenced by any one man—even one who could “box with the devil.”
Explore the timeless melodies of the past and discover more hidden histories behind your favorite classics.
References
- Martin, R. A. (2002). Hero of the Heartland: Billy Sunday and the Transformation of American Society, 1862-1935. Indiana University Press.
- Granata, C. L. (1999). Sessions with Sinatra: Frank Sinatra and the Art of Recording. Chicago Review Press.
- History.com Editors. (2010). Prohibition. History Channel.