“In Boston stingers are post-dinner drinks of which one’s not enough and three are too many” was printed in the Boston (MA) Globe on November 11, 1972. The saying usually refers to martinis and was made famous in the movie The Parallax View (1974), where this line was said by the character Gail (played by Doria Cook-Nelson), a worker at the Salmontail Bar:
 
“They say a martini is like a woman’s breast: one ain’t enough and three is too many.”
 
New York-based entertainment newspaper columnist Earl Wilson (1907-1987) wrote in October 1981:
   
“Henny (American comedian Henny Youngman—ed.) OK’d this: Martinis are like breasts. One is not enough and three are too many.”
 
The saying is sometimes credited to San Francisco (CA) journalist Herb Caen (1916-1997), but there is no early evidence that credits him. The martini saying has been printed on several images.
 
       
Wikipedia: Martini (cocktail)
The martini is a cocktail made with gin and vermouth, and garnished with an olive or a lemon twist. Over the years, the martini has become one of the best-known mixed alcoholic beverages.
 
H. L. Mencken called the martini “the only American invention as perfect as the sonnet” and E. B. White called it “the elixir of quietude”.
   
11 November 1972, Boston (MA) Globe, “Tech’s R and R sure to give BC recreation, but no rest” by Ernie Roberts, pg. 23, col. 2:
ATLANTA—In Boston stingers are post-dinner drinks of which one’s not enough and three are too many.
     
IMDb (The Internet Movie Database)
The Parallax View (1974)
Quotes
Gail: They say a martini is like a woman’s breast: one ain’t enough and three is too many.
 
30 October 1981, Indianapolis (IN) Star, Earl Wilson entertainment column, pg. 43, col. 3:
Henny (Youngman—ed.) OK’d this: Martinis are like breasts. One is not enough and three are too many.
     
Google Books
Killed Twice Buried Once:
A Story About the Catastrophic Apollo Fire
By W. Boyes
Rockville, MD: Chesapeake Bay Press
1986
Pg. 10:
Seeing him reminded me once again about that old adage concerning the imbibing of martinis which goes like, “Martinis are like breasts; one isn’t enough and three are too many.”
 
5 June 1988, Orlando (FL) Sentinel “Rambo III Casualty Count Excluding Audience Tops 100,” pg. 2:
Actually, we like one of the runner-up entries better (from a guy in New Jersey): “It has been said, Mr. Malle, that martinis are like women’s breasts . . . one is too few, and three are too many. Do you agree?”
     
10 May 1992, Los Angeles (CA) Times, “Whitey Herzog,” Magazine sec., pg. 34, col. 3:
He (Whitey Herzog—ed.) drains his drink and orders another. When it comes, he holds up the glass, and says: “Drinks are like a woman’s breasts. One ain’t enough and three are too many.”
   
Google Books
The Martini:
An Illustrated History of an American Classic
By Barnaby Conrad
San Francisco, CA: Chronicle Books LLC
1995
Pg. 120:
Richard “Mr. Rick” Fishman, founder of San Francisco’s floating party known as “Mr. Rick’s Martini Club,” says, “A Martini is like a woman’s breasts: one is not enough and three are too many.”
 
Google Books
The New Year’s Eve Compendium:
Toasts, tips, trivia, and tidbits for bringing in the New Year
BY Todd Lyon
New York, NY: Clarkson Potter
1998
Pg. 104:
Martinis are like a woman’s breasts. One isn’t enough, and three are too many. — CHINESE PROVERB — ANONYMOUS
   
Google Books
Bottled Wisdom:
Over 1,000 Spirited Quotations & Anecdotes
Edited by Mark Pollman
St. Louis, MO: Wildstone Media
1998
Pg. 71:
Martinis are like a woman’s breast - one’s not enough and three’s too many, unless it’s in the back for dancing!
Mark Pollman
         
Google Books
Comedy Quotes from the Movies:
Over 4,000 Bits of Humorous Dialogue from All Film Genres, Topically Arranged and Indexed
By Larry Langman and Paul Gold
Jefferson, NC: McFarland
2001
Pg. 116:
“You know what they say about martinis?” a bar girl asks Warren Beatty. “They say they’re like a woman’s breast,” Beatty replies. “Three are too many and one is not enough.”—The Parallax View (1974)
 
Twitter
Coco‏
@CocoGoesOut
And Orange Bitters. Is there a better drink? No. No, I say. “Martinis are like a woman’s breasts, one is not enough and three are too many.”
10:08 PM - 17 Aug 2007
   
7 October 2010, The Times (London, UK), “The danger of drinking dirty martinis: Fast drink” by Joanna Weinberg, pg. 9:.
My favourite witticism, most often attributed to Dean Martin but more likely to have come from the San Francisco columnist Herb Caen, is: “Martinis are like breasts—one is too few, and three too many.”
 
Google Books
The One That Got Away:
A Novel
By Melissa Pimentel
New York, NY: St. Martin’s Press
2016
Pg. 341:
“A wise man once said to me that martinis are like breasts. One is not enough, three is too many, but two is just right.”
 
Reddit—Jokes
Martinis are like tits…
submitted January 11, 2018 by jedi_jonai
Ones not enough and threes too many
(my grandpa’s favorite joke)