Those billboards plastering Times Square might be illegal

The billboards in New York City's Times Square might be iconic, but they also might not be legal. Dan Lewis of Now I Know pointed out this week that, under the constraints of the Highway Beautification Act of 1965 and its most recent update in May 2012, Times Square's bright lights and mile-high billboards aren't kosher.
The law aims to keep advertisements from inundating roads and becoming too large or distracting. The point, as the law's name so aptly puts it, is to keep America beautiful. Under the law, billboard sizes are limited to 1,200 square feet, which, The Smithsonian notes, is "smaller than many of the signs that cluster about the sidewalks in Times Square."
While Times Square might be crowded, it certainly isn't a highway. So how exactly does a Highway Beautification Act apply? Well, the U.S. government passed a law in May 2012 that included "urban principal arterial routes" under the law.
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The billboards bring in millions for the city of New York annually. Times Square's biggest billboard — a megascreen that's eight stories tall and spans an entire city block — costs advertisers more than $2.5 million to use for four weeks, which, according to The New York Times, makes it one of the most "expensive pieces of outdoor ad real estate on the market." That's why city officials are fighting to keep the ads — and the ads' revenue — in place.
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