Wilson was born in Evanston, Illinois, and was inspired by the work of the satiric "Mad" and "Punch" cartoonists, and 1950s science fiction films. His cartoons and prose fiction appeared regularly in "Playboy", "Collier's" and "The New Yorker" for nearly 50 years. He published cartoons and film reviews for "The Magazine of Fantasy & Science Fiction". From 1992 through end of publication, he prepared all the front covers for the annual book "Passport to World Band Radio". Wilson was a movie review columnist for "The Twilight Zone Magazine" and a book critic for "Realms of Fantasy" magazine.