Whit Stillman was born in 1952 and raised in Cornwall in upstate New York, the son of a impoverished débutante from Philadelphia and a Democratic politician from Washington D.C. Stillman graduated from Harvard in 1973 and started out as a journalist in Manhattan, New York City. In 1980 he met and married his Spanish wife while on an assignment in Barcelona, where he was introduced to some film producers from Madrid and persuaded them that he could sell their films to Spanish-language television in the USA. He worked for the next few years in Barcelona and Madrid as a sales agent for directors Fernando Trueba and Fernando Colomo, and acting in their films playing comic Americans as in Trueba's SAL GORDA. Stillman wrote the screenplay for Metropolitan (1990) between 1984 and 1988 while running an illustrating agency in New York and financed the film from the proceeds of selling his apartment for $50,000 as well as contributions from friends and relatives. Barcelona (1994) was inspired by his own experiences in Spain during the early 1980's, which was his first studio financed film. For The Last Days of Disco (1998) was loosely based on his travels and experiences in various nightclubs in Manhattan, and possibly at the Studio 54.

Was member of the dramatic jury at the Sundance Film Festival in 1995.