Throughout the 19th Century, the city's main entertainment district pushed northward. In 1798, the city's first major playhouse, the Park Row Theater, opened with a performance of Shakespeare's "As You Like It." The next move was to Astor Place, where the Astor Opera House opened in 1847; a major riot occurred in 1849, and dozens of rioters were killed and hundreds more injured. After the Civil War, several theaters opened up around Union Square, such as the Fourteenth Street Theater, the Union Square Theater and Walleck's (the demolition of Walleck's, then called the Star Theater, was recorded in 1901 by the American Mutoscope and Biograph Company). Next, the entertainment district moved to the Tenderloin (the Herald Square area); nearby on 28th Street was the famous Tin Pan Alley, where writers cramped in tiny rooms churned out vaudeville and ragtime songs for the area theaters and nightclubs.

The last major move northward was to Times Square, which was previously a major center for carriage manufacturing. The area was previously known as Longacre Square and when the Times building opened in 1904 it was renamed. Theaters, motion picture houses and vaudeville halls filled in the blocks, using massive electric billboards and buying ad space on the subway and El platforms to advertise to prospective customers. Hotels such as the Knickerbocker and Astor and numerous restaurants served the area, serving a burgeoning tourism industry that grew tremendously throughout the 1920s. However, the district's growth was slowed by the Great Depression and few new theaters opened, which marked the start of the area's decline. Throughout the 70s and 80s, the "Deuce" was lined with seedy sex shops, flophouses and peepshow, and many New Yorkers started avoiding the area.

In the mid-80s, several new projects broke ground in Times Square, including several new hotels and restaurants (many of which required the demolition of historic theaters). The tourism industry, growing again at a tremendous pace, focused on Times Square as the heart of New York City and encouraged people to visit and attend Broadway shows. This campaign, along with several other city initiatives to fight crime and clean up the area, was wildly successful and helped Times Square become a prominent attraction of its own. Now, most New Yorkers avoid the immediate area altogether, although there are some really great restaurants nearby on 46th Street's Restaurant Row.