The Bard of Analog Chicago: Steve Goodman - Absolutely Chicago Segway Tours

Chicago’s a really international town these days. We’ve got a world-famous mayor, we’re an international tourist destination, and soon we’ll be home to the biggest presidential library in the world. Our Cubbies broke the curse as the world cheered, and the industrial image that mayors like Big Bill Thompson and William Carter Harrison were attempting to shuck off at the turn of the last century is in the rear-view mirror. We have arrived.

But now that we are here with our beautifully landscaped front lawn, and our shimmering glass skyscrapers, many old timers look back. They don’t talk about the ‘Roaring ‘20s’ of Louis Armstrong or the ‘Gay ‘90s’ of Daniel Burnham. They speak about a time I like to call the ‘Analog Chicago.’  This was a time between Daley’s, pre-Ditka. These are times defined in history by the elements. There were no lights in Wrigley field, and a mayor’s career was assassinated by a snow storm. My parents grew up in this era. They remember Second City stars on TV every Saturday night.

The Bard of Analog Chicago

No artist captures Analog Chicago quite like Chicago’s lost troubadour, Steve Goodman. Known for a song called “City of New Orleans” about the north/south passenger train that brought King Oliver and Satchmo up from the Big Easy–Goodman was Chicago’s Faulkner. Charming, poignant, and without judgement, he talked of the city from the first person. He lived and breathed Cubs baseball and Northside culture.

So now that the Cubs are no longer “the doormat of the national league,” I’d like to look back at Analog Chicago’s great balladeer, Steve Goodman’s, and his greatest Chicago songs.

A Dying Cubs Fan’s Last Request

This song, more than any other, perfectly sums up this baseball team’s fans. The Cubbies just broke the 108 year old curse, but a lot of diehard fans couldn’t make it to 2016. The list includes Cubs announcer Harry Carrey, all-time great Ernie Banks, and my grandfather who lived all but ten of those cursed years.

Goodman serves as his own prophet of doom in writing this song. A true-blue loyal cubs fan, he knew the trials of a Cubs fan because he lived it. His song is rife with the slings and arrows of the misfortunes of Wrigley Field fandom. Like the man in the he tune tells, he died of leukemia and had his ashes laid in Wrigley’s hallowed soil. He was only 36 years old.

Lincoln Park Pirates

A darker tune with a lighter topic, this is one of the most Chicago stories possible. It would be unbelievable if it were true. Lincoln Park Towing has been plundering the streets of the windy city for more than 50 years. Ross Cascio’s, former owner/captain, and his merry band of thieves tow cars in legal and illegal parking alike, bring them back to their lair, and charge you $500 to set ’em free. Thanks to Alderman’s Ameya Pawar’s fight against the company, this may be last year that his song has meaning. Goodman’s tune stays true for now and is a simmering reduction of the purest Analog Chicago.

City of New Orleans


Trains and Chicago go together like Segways and fanny packs. Being the nation’s hub has enriched Chicago financially and culturally. We built grain elevators and elevated Jazz to the international stage with locomotives. “City of New Orleans” is an ode to the train they call the City of New Orleans. It is purely American and reverently melancholy. There are no words for how lovely this song is. Steve Goodman sang them all.

Go Cubs Go


Then there’s “Go Cubs Go.” Admittedly, this is my least favorite song. It has more cheese than a slice of Giordanos. The hand-jive-esque back beat, the obvious blues licks, the singalong… it’s perfect for a crowd of 30. It is a bar song to rival all of Ireland, but without a “frosty malt and a bag of peanuts,” it’s a disaster.

I do respect that this may be Goodman’s most famous song now that the 7th largest gathering of humans in civilization sang it aloud, but let’s also pay some respect to the other tunes as they are the lasting memories of Analog Chicago.


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