Tenderloin was a neighborhood of the West Side of Manhattan north and east of Chelsea on the far West Side, which stretched south to West 14th Street and up to West 57th Street, from the mid 1800s to the 1920s. It was primarily an African-American neighborhood. When the 23rd Precinct was built in 1907, the police commissioner's expressed his desire for a building to "look like a police station:" the unusual Medieval Revival style of the building, is more more commonly associated with armories, and forcefully asserted the authority of the police.

The raffish reputation of the Tenderloin's 1890s bordellos, repeatedly raided by Anthony Comstock's "vice squad" was sentimentally recreated in the somewhat kitsch 1960 musical Tenderloin, from the Fiorello! team: music by Jerry Bock and lyrics by Sheldon Harnick, the book by by the old master George Abbott and Jerome Weidman, based on a novel by Samuel Hopkins Adams.

With the construction of Penn Station, and new, cheaper housing in Harlem, much of the Tenderloin's Black community moved uptown by 1920.

It became an industrial area, but since the 1970s, with gentrification, the old Tenderloin's Chelsea and Hell's Kitchen (or Clinton) sections became increasingly residential again.

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• 23rd Precinct Station House A landmark building.
• Tenderloin