3. One Times Square, Home of the New Year’s Eve Ball, Is The Emptiest Building in Midtown But Wildly Profitable

When Lehman Brothers purchased One Times Square in 1995, they envisioned a new kind of tenant: advertisers. Instead of renting the offices inside the 25 floor building, they began retrofitting the facade with billboards. By 1997, the profits were up 400%, and the inside was empty.

So it remains 16 years later, hosting little more than a ground floor Walgreens and the office of Countdown Entertainment. The company, known for the New Years Eve Ball, organizes all Times Square entertainment on the last day of each year. In 2012, an appraisal note in One Time Square’s loan documents revealed its value at $495 Million, a staggering figure compared to the $27.5 million it fetched when it sold to Lehman Brothers in 1995. The New Year’s Eve ball is stored all year round inside One Times Square.

Here’s what One Times Square looked like back in the day:

One Times Square-Vintage Photograph-NYCPhoto by Brown Brothers in public domain via Wikimedia Commons