In July of 1986—eight years before Rudolph Giuliani took over as the city's Mayor—LIFE magazine visually documented Times Square, and its bevy of XXX-rated establishments. Here's what that summer in the Crossroads of the World looked like. An article in City Journal once noted that many are nostalgic for this old Times Square, because it "provided a harmless, playful way to subvert stuffy bourgeois morality." They counter that nostalgic longing, however, with the fact that in 1960 the New York Times was calling 42nd Street between Seventh and Eighth the "worst block in the city." Two years before these photos were taken there were 2,300 crimes on the block, with 20% of them being serious felonies. Could there ever have been a happy median between murder and Mickey Mouse?