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A Checkerboard Past

One great thing about ticket stubs, posters, and invitations is their ability to help us piece together the past with some precision. This relic below is the only way for me to know how I spent my evening 32 years ago tonight.

This invitation evokes memories of so many exhilarating experiences at the Checkerboard Lounge, a famous but long-gone blues club on Chicago’s South Side. The “New” in the name reflected a change in ownership after Buddy Guy, the blues legend who founded the club, moved on. But the club was still at its original location in 1989.

Going to this hole-in-the-wall on 43rdStreet – whether you call it a mecca, an oasis, or an alternate universe – was a transcendent music experience for many people, but especially for University of Chicago students of my generation. It was one of the last links to a vibrant night club scene when small clubs were ubiquitous on Chicago’s South and West Sides. These blues joints became the cradles of the electrified blues music whose influence on modern music remains immense to this day.

Magic Slim and the Teardrops headlined the show that night 32 years ago, and the “special guests” helped turn this event into a kind of South Side All-Star night. The name Junior Wells speaks for itself in the pantheon of blues musicians. Lefty Dizz had etched his name in all-time Checkerboard history in the fall of 1981, when he shared the stage there with Muddy Waters and a popular British rock band that had borrowed its name from a Muddy Waters song called “Rollin’ Stone.”

But one of my personal favorites that night was Andrew “B.B.” Odom, a regular at the Checkerboard. He was an underrated performer, a stirring singer with a surprisingly strong and rich voice. A chance encounter with him also helped me appreciate that clubs like the Checkerboard probably served as an oasis for the performers as well, and not merely for their fans. One day in the mid-1980’s, I was riding Jackson Park line on the Chicago “L” when I noticed a tired man sitting across from me. He wore work coveralls, and the four stars of the Chicago flag stitched on a patch gave me the impression that he worked for the City in some capacity. We made eye contact, and we both smiled and nodded to each without saying a word. It was B.B. Odom. I think he sincerely appreciated the unexpected recognition outside of the usual context.

By 1989 I had visited the Checkerboard so often that I’d lost count. In my book Blues Flashbacks, I offer a brief glimpse into how my “Checkerboard Past” began during my second year of college. Here is a short excerpt:


I felt a faint connection to the Checkerboard and blues in general, after someone mentioned that the Rolling Stones dropped by there once to join Muddy Waters onstage. The Stones were on the tour to support Tattoo Youand had a history of seeking out the famous Chicago bluesmen when they came to town.

The night my friend Jeff and I went there in January 1983 was like an initiation for me, with indelible images: the dark streets with the once-elegant, abandoned buildings we rode past on the cab ride; a parking lot across the street with a huge chain link fence topped with concertina wire; the unmistakable sound of blues music, audible as we left the cab and headed toward the door, where a guy named Anthony greeted us with a smile and a handshake.

Anthony collected our money and escorted us in. In the right corner, club manager L.C. Thurman played cards with a few other men. Next to them along the right-hand wall was the bar. The small room – Buddy Guy says in his book that the capacity was about 65 – was filled with mismatched tables and chairs. In the small crowd that night were two famous professional athletes whose names I won’t mention. The stage was along the wall on the street side, graced by one lonely light bulb hanging naked from the ceiling.

I don’t remember who played that first night, but I was hooked. You could say I became obsessed, because I did start researching the music as best I could. I spent far too much time and money at the Checkerboard over the next four or five years, during and after graduation from college.

As far as I know, the Checkerboard on 43rd Street represented the last stand for influential blues clubs on the South Side. The names of the acts we saw under the lightbulb at the Checkerboard may have never achieved the international fame of a Buddy Guy or a Junior Wells, or even national fame for that matter. But for all of the University of Chicago students who perused The Reader to see who was playing at the South Side clubs, these guys had star status. First and foremost come Magic Slim and the Teardrops, who released a few popular singles, but otherwise never basked in the mainstream limelight. My friends and I would also make a special effort to see Dion Payton and the 43rd Street Blues Band, and the multi-talented Lucky Peterson, and the hit-or-miss antics of Lefty Dizz. We probably saw Buddy’s brother Phil Guy perform at the Checkerboard more than we saw Buddy himself.

By the way, in all those years and all those visits, we never learned Anthony’s last name.


The Checkerboard no longer exists, but its legacy lives on in many ways in Chicago. Let’s fast forward to a night at Kingston Mines, a club on Chicago’s North Side. It’s a Saturday night in September 2018, and Shawn Holt is sharing the billing with Joanna Connor. Holt has become a fine blues guitarist in his own right, and that might be partly due to genetics. He is Magic Slim’s son. The picture below shows him playing that night at Kingston Mines.

Joanna Connor once played in the 43rd Street Blues Band. My friends and I first saw her perform at the Monday night jam sessions at the Checkerboard in the mid-1980’s, shortly after she arrived in Chicago from Massachusetts.

As 2021 gets underway, Connor is launching a new album called “4801 South Indiana Avenue,” produced by Joe Bonamassa. What does that address mean? It marked the home of another famous South Side Chicago blues club, Theresa’s, which I had the pleasure of visiting only once at its original location. But that’s a story for another day.

Frank Luby worked as blues music reviewer from 1983 to 1992 in Chicago, Cleveland, and Boston. He has interviewed all-time blues greats such as B.B. King, Willie Dixon, Stevie Ray Vaughan, Junior Wells, Albert Collins, Koko Taylor, and Buddy Guy.

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