7. P.J. Clarke’s (1884)

P.J. Clarke's, one of the oldest bars in NYC

Dating back to 1884, P. J. Clarke’s has been a staple of the East side for more than a century, and its history has been recounted to almost mythic proportions. In the 1940s Johnny Mercer wrote his song “One For My Baby” on a napkin at P.J. Clarke’s, and a young Sinatra regularly ended nights here. Buddy Holly proposed to his wife there and Keith Richards gave an unplanned performance of “Brown Sugar” at the bar. It is has also served as the location for numerous films, including The Lost Weekend and Annie Hall, and the television series Mad Men.

The bar is named after its second owner, Irish immigrant Patrick J. Clarke, who bought it in 1912. As a holdout, the two story establishment stands in particular contrast to the skyscrapers that surround it. The upper floor houses Sidecar, a restaurant that provides a more refined dining experience.