To say that 8 Spruce is ugly is a joke. The building is very unique as it looks like it is melting from up close but glistening in the sun from afar. Totally un-cookie-cutter. CitiCorp Center epitomizes Italian minimalism making this a classic building in the NYC skyline. Its 45 degree sloped crown made a huge architectural statement denying the skyline of a spire or flattop cap. Back in 78' it was one of a handful of buildings that dominated the skyline. 550 Madison, the former Atlantic Bell corporate headquarters has that classic Chippendale crown and a beautiful lobby. 2 Columbus Circle is definitely weird, but what better way to house the museum of arts and design in a building that is avant-garde in its architecture.
If I had to make a list of ugly buildings I'd say Madison Square Garden which looks like a giant cesspool, 450 West 33rd, 3 Park Avenue, The AT&T Long Lines Building, 375 Pearl, 1250 Broadway and 4 New York Plaza should be included.