3. The Playpen

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While once Times Square was filled with places like The Playpen, a sex emporium selling porn and sex toys and offering live peep shows, it is now a rarity. The store is one of less than ten sex shops remaining in the district. Many adult entertainment shops were closed down in the 1990s due to strict regulations enforced by Mayor Giuliani to clean up the area. Sex related businesses couldn’t operate within 500 feet of residences, schools, places of worship or other sex related businesses. Later, the rules were loosened and stores with at least 60 percent non-X-rated merchandise were not technically considered adult entertainment businesses.

The Playpen was originally located inside a theater at 693 8th Avenue. The theater opened in 1916 as the Ideal Theater and was known by a series of names after that including The Cameo, Squire Theater and The Adonis. The store was connected to The Funny Store, a gag gift and magic shop which helped the Playpen comply with the 60/40 rule. The Playpen moved a few doors down to its current location, on Eighth Avenue between 43rd and 44th Streets, in 2007 when the theater was demolished. Today, the former site of the theater is a Shake Shack.