The Chesterfield cigarette brand was one of the most popular brands of cigarettes in the United States for a good part of a century. In the early twentieth century, the Chesterfield cigarettes brand was created, named after the Chesterfield county of Virginia. Chesterfield non filtered cigarettes are very strong and the Chesterfield cigarette brand became well known for this during the mid twentieth century; during this time they were famously smoked by James Dean, Humphrey Bogart and Lucille Ball. Chesterfield regular cigarettes became one of the three most popular of all cigarette brands in the United States during the golden age of cigarette advertising during the fifties and sixties.

One popular series of Time Magazine Chesterfield cigarette ads during the late sixties featured the advertising slogan "one silly millimeter longer"; during this period many companies were coming out with new brands of cigarettes that were one hundred millimeters long, so Chesterfield released a new cigarette that was one hundred and one millimeters long. The slogan for the ad campaign was sung in the television and radio commercials to the tune of the popular song "La Bamba", and was one of the last of the classic cigarette advertisements before cigarette advertising on radio and television commercials was banned by the United States government at the beginning of the seventies. Since then the Chesterfield cigarette has been advertised on banner ads / bill board advertisements and in magazine cigarette advertising campaigns; this, however has failed to allow the Chesterfield cigarette brand to retain the recognition that it once had among American smokers.

In recent decades, the Chesterfield cigarette has dropped in popularity until today few people in the United States are aware of the brand any longer; however, it is easy to see the Chesterfield cigarette in classic films from the fifties and sixties such as "The Gold of Sierra Madre", "Bonnie & Clyde" and "Breathless". Also, the Chesterfield cigarette company was a sponsor of many episodes of the popular supernatural mystery / thriller show "The Twilight Zone" and the Chesterfield cigarette brand would be advertised by Rod Sterling with the phrase "there's no denying the smooth taste" after some episodes. While it is harder than before now to even find the Chesterfield cigarette in stores in the United States, cheap Chesterfield cigarettes can still be found on the world wide web and the Chesterfield cigarette brand is still popular throughout Europe.