The Hotel Pennsylvania was built by the Pennsylvania Railroad and operated by Ellsworth Statler. It opened on January 25, 1919 and was designed by the firm of McKim, Mead & White, which also designed the original columned version of Penn Station located across the street. (The old Pennsylvania Station was razed in 1963 to make room for Madison Square Garden and the redeveloped below-ground station in use today.)
The hotel was acquired by the Hotels Statler Company in 1948 and renamed the Hotel Statler. Following the sale of all 17 Statler hotels to Conrad Hilton in 1954, the hotel became The Statler Hilton. It operated under this name until the early 1980s, when Hilton sold the hotel. It was renamed The New York Statler for a brief period, and was operated by Dunfey hotels, a division of Aer Lingus. It was then purchased in 1984 by the Penta Hotels chain, a joint-venture of British Airways, Lufthansa and Swissair, becoming The New York Penta. In 1992 Penta went out of business and the hotel was returned to its original name, Hotel Pennsylvania.
The hotel has the distinction of having the New York phone number in longest continuous use. The number, PEnnsylvania 6-5000, is the inspiration for the Finegan, Gray, and Sigman song of the same name. The most popular version was performed by Glenn Miller with the Andrews Sisters not far behind. Many big band names played in the hotel's Cafe Rouge Ballroom, including the Dorsey Brothers, Count Basie, Duke Ellington, and the Glenn Miller Orchestra.
Contrary to common practice, there is a 13th floor. The hotel states it has 22 floors from street level to the roof, plus three additional levels in the penthouse. The highest penthouse level is numbered as the 21st floor. The discrepancy in floor numbering is due to several mezzanine-type levels that carry names such as "lobby mezzanine" instead of floor numbers.
The threat of the Hotel Pennsylvania's demolition was first introduced in the late 1990s when Vornado Realty Trust bought the hotel. Vornado announced in 2007 that the hotel was to be demolished to make way for a new office building with Merrill Lynch as its anchor tenant. Owner Vornado Realty Trust intended to build a 2,500,000-square-foot (232,000 m2) building by 2011. The site is the only remaining area in Midtown Manhattan that would not require special permits for development of a new office project of that size.
Shortly after the announcement of Vornado's plans, the staff of ', a magazine which sponsors biennial HOPE hacker conventions at the hotel, began investigating possible ways to save the hotel from demolition. They were joined by the new Save the Hotel Pennsylvania Foundation, whose members included a number of city organizations and politicians to aid in the landmarking of the hotel, including The Historic District Council, Manhattan Community Board 5, and Assemblymen Richard Gottfried. In November 2007, Manhattan Community Board 5 voted 21-8 to have New York City Council landmark the historic hotel. However in February 2008 the New York City Landmarks Preservation Commission denied the request for landmarking.
Preservation efforts have proven difficult. Emmanuel Goldstein of 2600 noted that while people overseas expressed concern over the fate of the hotel, "New Yorkers might not care enough to get involved. The hotel was old; the rooms weren’t as big and luxurious as other more modern facilities; and New Yorkers simply weren’t in a position to grasp the importance of such a place since they normally don’t need cheap and easily accessible hotels if they already live here."
- December 1925 William Faulkner stayed at The Hotel Pennsylvania while writing one of his many novels. Later he would go on to receive the Nobel Prize for Literature.
- November 17, 1935 Herbert Hoover spoke before the Ohio Society of New York at the Hotel Pennsylvania
- In 1940, Glenn Miller and the Glenn Miller Orchestra began the first of several extended engagements at the Hotel Pennsylvania's Cafe Rouge, often broadcast live on NBC Radio. Recordings of several of these engagements were released by RCA Victor.
- In December 1942 Charlie Chaplin attended a dinner at The Hotel Pennsylvania in New York sponsored by Russian War Relief
- In 1953, Dr. Frank Olson jumped through the closed window of his 10th floor room. Olson worked for the CIA and it is believed he was involved with experiments to study the effects of LSD.
- On November 3. 1964, former Attorney General Robert F. Kennedy addressed his supporters in the hotel (then the Statler Hilton), after capturing the seat of incumbent Kenneth Keating in the United States Senate.
- The character "Statler" of Statler and Waldorf was named after the hotel, when it was the Statler Hilton.
- In June 2002, Dave Barry wrote a column about his experience at the thinly-disguised "Hotel Shpennsylvania".
- The Hotel Pennsylvania appeared in the 1986 film The Manhattan Project, as the setting of a science fair. Rather than construct a set and populate it with actors, the filmmakers hosted an actual science fair in the hotel, and simply filmed as it was going on.
- In 1997, The grand ballroom became NEP/Image TV Studios and is where the television shows such as Maury, Sally Jessy Raphael, 2 Minute Drill, and The People's Court have taped.
- In 2009, old studios in the hotel were rebuilt and consolidated into a new 10,000 square foot studio for the sitcom Sherri.