It’s not easy to make a suspension bridge look clunky, but the Williamsburg Bridge somehow manages. Similarly, it’s not easy to make a 55-story, 693-foot skyscraper appear squat and clunky, but the (former) Lincoln Building, completed in 1930, at 60 East 42nd Street gives a good try:

It was the sixth tallest building in the world (and the fifth tallest in NYC) when completed, although the topping out of the 500 Fifth Avenue, 20 Exchange Place, and the Empire State in 1931, 70 Pine Street in 1932, and 30 Rockefeller Plaza (AKA the RCA Building) in 1933 pushed it down that list pretty quickly.
I’m not sure why it feels so off to me. Maybe some combination of the out-of-character gothic arches at the top, the out-of-scale bracketed cornice at the very top, and the lack of east-west setbacks? From the street up to three stories below the first setback it’s got a functional semi-moderne vibe, and then it switches to too-small details at the setbacks. It’s been repositioned upscale in recent years: it used to be a rabbit warren of lowish-end undifferentiated office space. I had a summer job there between high school and college and the floor (if I recall correctly, the floor was in the teens) was a huge dark maze.
We’re looking at a couple of better buildings right behind it (the Lefcourt Colonial Building at 295 Madison Avenue, and 275 Madison) and then a bit further away, the Empire State Building. The low-rise building with the steep hip roof and smoke plume is the Murray Hill Hotel.
The Wurts Brothers titled this photo “General View – Manhattan – Aerial view – East 42nd Street – looking southwest” but of course it’s not. We’re not up in the air: we’re looking out a window of the Commodore Hotel. The low roof in the bottom right is Grand Central Terminal, the Lincoln Building’s reason for being, and just to the left of the Lincoln Building at the bottom you can see the back of the statue of Mercury on the terminal’s south facade.

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