If I'm going to discuss tall buildings, might as well get this out of the way. Skyscrapers are not penises unless you have a very strange definition of "penis." Most have flat tops and rectangular footprints, many of the remainder have spires ending in points. (Everyone together now: ouch.)
Except, of course that some are. The current champion, in my opinion, is the Williamsburg Bank on Flatbush Avenue in Brooklyn. Tallest building in Brooklyn from the late 1920s until last year and a big old dick:
The a/c equipment for the building is under the dome, and in cold weather it vents steam...you get the idea.
The all-time champion was the Singer Building, the headquarters of the sewing-machine company, which was demolished for a rather boring black steel-and-glass building. It had a large base with a curved mansard roof, a 65-foot square tower, and then another curved mansard on top of the tower.
Singer, in its rampant glory: