You know this Don Draper look-alike isn’t looking to go see a show or do any shopping, the type of “pleasure” Sheraton suggests can be mixed with business during a stay in New York. No, this ad taps directly into the one-track mindset of the 1950s traveling businessman. What’s great about this ad is it deviates from the typical 1950s and early 1960s hotel advertising formula of featuring the building and talking about how tall it is, how many rooms it has, or any number of stats that don’t speak to that amazing feeling you have when you look out your hotel window and think: “what kind of mischief can I get into in this amazing city?”.

FUN FACT: In 1957, New York’s Park Sheraton (now Park Central Hotel and no longer a part of the Sheraton family) was the site of an infamous mob murder. Albert Anastasia of the Gambino crime family, was shot several times in the hotel’s elegant barber shop. (Source: Concierge.com)