[1] The stinger was a popular drink during Prohibition in the United States, for crème de menthe could mask the taste of the inferior-quality brandies then available.

[12] Cognac, a type of brandy, was identified as the basis for the stinger as early as 1905 in William "Cocktail" Boothby's supplement to his 1900 book, American Bar-Tender.

[6][21][22] The stinger's popularity in New York City was so great that urban legends attributed the cocktail's genesis to famous millionaire Reginald Vanderbilt.

[25] The vodka stinger was the drink of choice for Joanne in the musical Company by Stephen Sondheim, with her calling for one in the song "The Ladies Who Lunch".

Dudley the angel (played by Cary Grant) orders a round of stingers while lunching with ladies from the church in the 1947 film The Bishop's Wife.

[30] The evolving stinger (used with green rather than white crème de menthe) forms a plot point in the 1948 film The Big Clock, when George Stroud (Ray Milland) orders one and a random woman in the bar (Rita Johnson) already knows his name.

[31] In the 1950 Humphrey Bogart and Gloria Grahame film In a Lonely Place, Dix Steele's lush friend Charlie orders a stinger at Paul's bar before the first fight scene.

In the 1956 Bing Crosby and Frank Sinatra film High Society, Dexter-Haven's butler offers Stingers at lunch to those who over-indulged in champagne during the previous evening's party.

[32] Cary Grant again orders stingers ("and keep them coming") as he tries to tolerate character Alice Kratzner's (Jayne Mansfield) empty-headed babbling in the 1957 comedy film Kiss Them for Me.

[33] Mr. Dobitsch (Ray Walston) instructs his Marilyn Monroe look-alike date (Joyce Jameson) in the 1960 film The Apartment to not spill the glasses of stingers she is holding as they exit their cab and enter C.C.

"[34] In the 1983 film Gorky Park, William Hurt orders a stinger, and Brian Dennehy makes a rude remark indicating that the drink is not reputable.