“So when you come out of Penn Station, look up. Our building is the one that has a big painting on it.”

“A painting? What of? Like a…” and then they name the first artist they think of. Picasso. Michaelangelo. Rembrandt. Cave drawing.

“No, no, just like a hand-painted ad that covers the entire side of the building. I think it was cigarettes last time I looked.”

“Oh, it changes?”

“Yeah, like every month or so. You’ve been through Penn Station before haven’t you? Didn’t you ever notice the building a two blocks north of there with the big-ass painting on it?”

To which the person I’m talking to embarassedly admits that, no, they never noticed a giant, 20-story painting looming over Penn Station. Which brings us to our usability lesson for the day:

New Yorkers never look up.

Which is a shame. Because, while paintings on the south face of the Eli Haddad building have, over the course of the last 30+ years become a source of secondary revenue for our landlord, there was a time in the not too distant past when signage painted on the sides of Manhattan buildings seem to have had real moxie. While I’m hardly the most accomplished photographer on staff, here are some business advertisements from around the neighborhood that, in several cases, may have outlived the businesses they peddle:

Right down the street, The Kaufman Management Company hasn’t gotten around to adding the last 2 digits of their phone number back to their sign since the hotel next door went in.

An ad for an indoor ice rink in this building near the post office. I think the rink itself has relocated to Chelsea Piers; at least the Sky Rink brand has.

I’m not sure what the Sable Brothers do but, their location squarely in the middle of the Fashion District, it’s safe to assume it involved dead foxes.

Insert your own joke about ‘Entertaintments’, proofreading and the effort involved in updating a typo once it’s on the side of a building.

View from the Flatiron Building, looking north.

C.O. Bigelow has the most deliberate olde timey typography of all the building adverts I remember seeing.

Enjoy.

EDIT 4/24 12:07pm: Photo submitted by longtime fan Em-dash: