Hugh Hamilton Wilson, Jr. was born in Miami, Florida. He attended Coral Way Elementary, Ponce de Leon Jr. High, and Coral Gables Sr. High, where he was a member of the Ching Tang Fraternity. He entered the University of Florida in 1961 and graduated in 1964 with a degree in Journalism. At Florida, he was a member of Blue Key Honor Society and president of his fraternity, Phi Delta Theta. Wilson received the school's Distinguished Alumnus award in 1982. He has also served as a guest professor of Media Studies at the University of Virginia.
In 1966, he entered the advertising business in Atlanta at the Burton-Campbell Agency. He was a copywriter before becoming creative director in 1970 and president in 1973. Tom Patchett and Jay Tarses, producers of the Bob Newhart Show, were instrumental in getting Wilson a position with Mary Tyler Moore Productions in 1975. They, along with Grant Tinker, gave him his first writing assignment for the Bob Newhart Show in early 1976 and in 1977 made him a co-producer of the Tony Randall Show. In 1978, Wilson created WKRP in Cincinnati (1978-1982) for CBS. Two of his WKRP scripts won Humanitas Prizes and the show was nominated twice for the Emmy in the Best Comedy category. The character of Bailey Quarters on WKRP was based on Wilson's wife. Wilson attempted to break into movies by re-writing a low-budget comedy on the condition that he could direct it. The result was the first Police Academy for the Ladd Company (Warners) and producer Paul Maslansky. It was a surprise hit of 1984. In 1985, Wilson shot the singing cowboy comedy Rustlers Rhapsody, starring Tom Berenger and Sela Ward. The movie was filmed in Spain. “I grew up watching Roy and Gene and Hopalong Cassidy,” Wilson said in the production notes. “That was my idea of a movie.” The movie failed at the box office but has gained a strong cult following over the years. The same year, he created the short-lived television series Easy Street starring Loni Anderson. In 1988, Wilson returned to CBS to create and co-produce with Tim Reid the highly regarded but short lived (22 episodes) Frank’s Place. Along with The Days and Nights of Molly Dodd (created by Jay Tarses) the two shows were the first to be done in the style that has come to be known as “dramedy.” Wilson received three Emmy nominations for Frank’s Place and won the Emmy for Best Writing. Wilson also created the CBS show The Famous Teddy Z (’89) and directed the movies Guarding Tess (’94) and Blast from the Past (’99). In 2001, Wilson and John Grisham teamed up to make Mickey, an independent movie about little league baseball.
Wilson married Charters Smith in 1979. They have five grown children. Daughter, Caroline Charters Wilson, is an actress and singer. Wilson moved to Virginia in 1992 and sometimes teaches screenwriting at the University of Virginia. He is a Roman Catholic.