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Upper West Side Historical Photo Challenge: Bonus-Edition Followup

April 3, 2026 | 11:40 AM
in COLUMNS, HISTORY, NEWS
0

By Rob Garber for the Bloomingdale Neighborhood History Group

OK, these AI fakes fooled approximately nobody!  But what exactly was wrong with them?  The image purporting to look down the Hudson gave you more opportunities to find flaws: Where does Riverside Park ever undulate so noticeably, and what ship captain in their right mind would head straight for a shoreline lacking any evidence of piers with all their sails set?  Most Upper West Siders know their church spires, but there is and was none that looked like the one near the upper left corner.  It’s tough to reconcile midtown skyscrapers with 19th century sailing ships unless they had time travelled from Op Sail 1976.  And what’s with New Jersey?  There hasn’t been a protuberance like that on the Jersey coastline since Chris Christie went sunbathing.

The Broadway scene was a bit more convincing, I thought.  The buildings are low enough and the street traffic sparse enough that this could be from before 1900, in which case you wouldn’t expect a wall of 15-story buildings along West End Avenue or Riverside Drive, so that was plausible.  But there’s something wrong with Riverside Park—too flat, too broken up.  And where would WEA run into the park the way it does in this image?  There’s a cross street in the foreground, but even though there are regular breaks in the center island, the cross streets never quite materialize as you scan uptown.  The more you look, the more the scene becomes generic, like the streetcar-ish vehicles.

Let’s flip on their heads the obvious deficiencies you caught, and ask a different question: How soon will this kind of fakery become essentially impossible to detect?  These were created with a few minutes of prompts by a complete AI amateur, at the dawn of AI image generation.  This wouldn’t have been possible just a few years ago; imagine how much better it’s going to get very soon!  Historical research will become more fraught and less fun when you don’t know what you can trust.

Shout–out to Readers: Henry, Jay, and Ron Wasserman were struck by the sailing ships too close to shore.  Elgin 93 noted that Riverside Drive was too straight.  Steevie caught the lack of cross streets by and the unvarying vehicles on Broadway.  Hat tipto ecm for giving us Slopville, the West River, and Moses Avenue.

About the author:  Rob Garber has lived on the Upper West Side since the late 20th century and is a member of the Bloomingdale Neighborhood History Group. To learn more, visit their website at upperwestsidehistory.org. All photos in Upper West Side Historical Photo Challenge are used by permission.

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