Gramercy Park Hotel was designed by Robert T. Lyons and built by the developer brothers Bing & Bing from 1924–1925, with a westward extension along Gramercy Park North – a continuation of East 21st Street – designed by the firm of Thompson & Churchill and built in 1929–1930. Both wings were designed in Renaissance Revival style. The hotel occupies the site of the former homes of the flamboyant architectStanford White, political leader and defender of agnosticismRobert Ingersoll and lawyer-diarist George Templeton Strong. Humphrey Bogart married his first wife Helen Menkenat the hotel, and the Joseph P. Kennedy family, including a young John F. Kennedy, stayed on the second floor for several months, before the family moved to London so the elder Kennedy could take up his post as the American ambassador. During the Great Depression, Babe Ruth was a regular bar patron – an autographed picture of Ruth hung in the bar until it disappeared in the 1960s – and when James Cagney and his wife lived nearby at 34 Gramercy Park, they were frequent diners at the hotel. In the 1940s, Edmund Wilson lived in the hotel with novelist Mary McCarthy, and humorist S.J. Perelman maintained his residence there, dying in his room in 1979. In 1958 Herbert Weissberg, a prominent New York hotel owner, bought the hotel. He added a gift shop, doubled the size of the bar and gave tenure to Pinky, the beloved hotel bellhop. Guests were drawn to its bohemian character, low prices and locale. The hotel's reputation for discretion attracted such musicians as Bob Marley and Bob Dylan in the 1970s. The Canadian and Chicago part of the first cast of Saturday Night Live stayed in the hotel during the show's premiere and Paul Shaffer, the show's original bandleader, continued to live in the annex for another 16 years. Other former residents include character actress Margaret Hamilton, actor Matt Dillon, and playwright David Mamet. Other notable guests include the Clash, Madonna, Debbie Harry, and David Bowie. By the late 1990s the hotel's ratings began to decline, as Weissberg's health began to fail. His sons fought for control and, after a series of family tragedies, the hotel was subleased in 2002 to Steven Greenberg, the founder of the Roxy nightclub. A bar was added to the roof but the restaurant closed. It began to attract a younger clientele and the prices began to increase rapidly. Following Weissberg's death in 2003 Gramercy Park Hotel was sold to Ian Schrager, who renovated the hotel in collaboration with artist Julian Schnabel. Schnabel designed the interiors, many fixtures and furniture pieces throughout the hotel. In 2010 Schrager sold his interests in the hotel and is no longer affiliated with it. Gramercy Park Hotel is currently owned by the real estate firmRFR Holding LLC, and operated by Manhattan Hospitality Advisors. The Rose Bar anchors the hotel, along with the Jade Bar and rooftop Gramercy Terrace restaurant. It is also home to Danny Meyer's Maialino, which serves Italian cuisine. The hotel continues to exhibit paintings by noted artists, including Jean-Michel Basquiat, Damien Hirst, Richard Prince, Julian Schnabel, Cy Twombly and Andy Warhol.
Renowned Argentine rock musicians and singer-songwriters Charly García and Pedro Aznar, two of the most important artists in their country's history, jointly created the song Gramercy Park Hotel, as a track in their 1986 maxi single albumTango. Hotel Gramercy Park, a documentary directed by Douglas Keeve, premiered at the Tribeca Film Festival in April 2008, chronicles the hotel's history during the Weissberg era, the turmoil that plagued his family, and Schrager's renovation.