KOOL is a brand of menthol cigarette currently produced by the R. J. Reynolds Tobacco Company, introduced in 1933, that has marketed itself towards the "sophisticated man". Originally introduced as an unfiltered "regular" size (i.e., short) cigarette, filtered 85 mm king-size versions were later added to the lineup as filtered cigarettes gained popularity in the 1960s. Since then, mild (milder menthol flavor), light (reduced tar), and 100 mm long varieties have been introduced. Nat King Cole, who died of lung cancer at the age of 45, was known to chain-smoke Kool cigarettes, which he believed to have a beneficial effect upon his singing voice.
Kool cigarette advertising began with the character of "Willie" the penguin who was portrayed as several different professions, among which were a doctor, a soldier and a chef. In the early 1960s, the image of the cartoon penguin was no longer used, and Kool instead began marketing their cigarettes by linking the cool taste of menthol to cool outdoor scenes portraying water or snow.  In the newest Kool ads, male/female encounters and sports references are prominent. Former Kool Models include Steve Tyler.