The summer after 8th grade, I went downtown a few times a week to take classes at the School of the Art Institute of Chicago Young Artist’s Studio program. The photo silk screening class was in the Pakula building at 218 S. Wabash. The painting class was in a studio on the campus building behind the Art Institute. On occasion, I would shop at the Woolworth’s on State Street and the Stop & Shop at 16 W. Washington. When I was about 18, I summoned the courage to walk into an X-rated book store located on Randolph near State, if memory serves me right. I hightailed it out of there when a freaky guy in a trench coat leered at me. Perhaps he would have flashed me, or my vivid imagination got the better of me. I was fascinated by Randolph Street, in particular the block between State and Dearborn. It had a similar kind of sleazy charm as Times Square in the 1970s, albeit on a tiny scale. The photographs featured in this blog provided inspiration for businesses to include and a search for materials such as matchbooks, postcards, and menus. This ephemera offers a glimpse at a street that was once vibrant and thriving with an incredibly cool and eclectic array of businesses. Sadly, by the time I ventured downtown, most of these businesses were long gone or had lost their luster. I primarily researched businesses between State and Randolph, west to LaSalle. Of course the beautiful Chicago Cultural Center’s north lobby is on Randolph at Michigan.