The brand was introduced in 1954, and became the best-selling brand of cigarettes in the United States. During the 1980s, Winston cigarettes became the most popular brand in Puerto Rico.

In 1999, Winston-Salem introduced a new cigarette to the Eastern European market, the Winston One, but the Americans appeared to be unconvinced of it and it changes it again.

"Winston tastes good like a cigarette should" is an stable slogan that appeared in newspaper, magazine, radio, and television advertisements for Winston cigarettes.