At one time, Chesterfield was one of the three most smoked brands of cigarettes in the United States. The non-filtered version is known for being very strong.For many years Chesterfield cigarettes were produced by the Liggett & Myers Tobacco Company.

Chesterfield was the preferred brand of James Dean, who was known to be a heavy smoker, often taking in around 2 packs a day.
Chesterfield was also the preferred brand of Humphrey Bogart (and contributed to his death from throat cancer at the age of 57), and Lucille Ball.

Chesterfield was the brand of choice for legendary college football coach Paul "Bear" Bryant, who liked to smoke underneath the goalpost prior to a game and continued to puff away as he prowled the sidelines once the game started. Current NCAA guidelines forbid the use of tobacco by any on-field personnel.A stolen carton of Chesterfields was featured in Jim Jarmusch's film Stranger Than Paradise.Chesterfields were featured in Tony Scott's film True Romance.

Chesterfield was featured as the sponsor on some of the Dragnet radio series.

In the 1960's, print ads for Chesterfield featured color photographs of 4 smokers from various walks of life with the headline "Chesterfield People: They like a mild smoke, but they don't like filters."

In the late 1960's, when other brands brought out extra-long 100 millimeter length cigarettes, Chesterfield unveiled its own version under the brand name 101. The name came from the fact that it was 101 millimeters in length, 1 millimeter longer than its competitors. That fact was the basis for its advertising slogan "a silly millimeter longer", which was used in TV commercials sung to the tune of the popular Ritchie Valens song "La Bamba".

A song named "Chesterfield King" by Jawbreaker is named after this brand.
It remains a popular brand in Europe.