After a lifelong friendship, Paul Simon and Art Garfunkel formed a singing duo, calling themselves Tom & Jerry. Their first efforts echoed the sounds of the Everly Brothers; they experienced some mild success with a song called "Hey Schoolgirl" before taking a break and going off to separate colleges. A few years later, they reconnected in the crowded houses of the Greenwich Village folk music scene and began comparing notes on compositions they'd been working on. These later became cuts on their first post-Tom & Jerry album release, Wednesday Morning, 3 A.M. One of them was "Bleecker Street."
The resulting album eventually climbed to #30 on the Billboard charts, but "Bleecker Street" never made a splash, though many claim it is one of Simon & Garfunkel's overlooked masterpieces and a fine example of what embodies pure folk music. The song with the deep impact was "The Sound Of Silence," which was released with various overdubs and became a #1 hit.
Bleecker Street is a real street in Greenwich Village, New York, named after a real family - the Bleeckers - who owned a farm in the early 1800s. When they signed over their property to the city, they had no idea how famous their name would become, synonymous with upscale boutiques and eateries that now line the street.
The line, "$30 pays your rent on Bleecker Street" is shocking to anyone who has been to the neighborhood, where you would be lucky to find an apartment for less than $2000 a month.
Paul Simon, who wrote this song, has said that it is more representative of the New York folk sound of the times than of his particular talents. He says that while many lesser-known songwriters had one or two standout songs, for the most part, everybody of that period was writing the same thing.