East 55 St, Midtown

East 55th starts off with quite a bang. The corner of 55 and 5th is the very famous St. Regis Hotel. It was built in 1904 is a very old, elegant hotel. It boasts a giant celebrity clientele especially from the Golden Era. Hemingway, John Lennon, Astor, John Huston are some of the few. Marilyn Monroe also stayed here during the Seven Year Itch -- she, reportedly, kept the entire floor up all night fighting with her husband over the celebrated subway grate scene. One block east is another building with a huge celebrity contingency: the Friar's Club. The Friar's club is somewhat of an actor's fraternity that is famous for its Roasts. They didn't allow women until the late 80's and it's quite prestigious for actors. The building, itself, is really beautiful too. It's an old townhouse. I would love to go to a roast here.
Directly across the street is where the most famous whorehouse in the city was until 1930. Seemed like an odd place, at first, to me . . but, I guess the location made the commute much easier for all of the uptown richies looking for a good time. There's another big brothel at 55 and Lexington but I guess the reputation of that was overshadowed by the Chinese restaurant on the ground floor that invented General Tsao's Chicken.
PJ Clarkes (the original one) is at 55 and 3rd. I have yet to go to this one but it has been around since 1868. The Downtown one is pretty cool for happy hour but I'm sure this one is the best given the history of the building and it being the original.
Not a jam packed street but there is some really great history as far as big buildings go. It's a pretty cool street to hit up for drinks.