Mary Pickford (1892-1979) was a silent film star, nicknamed “America’s Sweetheart.” She married actor Douglas Fairbanks (1883-1939), and it was probably during a 1922 trip to Cuba that the Mary Pickford Cocktail originated. “We lunched with the Hicklings at the Sevilla, well, off red snapper and heart of palm salad, with a Mary Pickford cocktail” was cited in print in 1926. “The Mary Pickford, invented during a visit to Havana of the screen favorite by Fred Kaufman, is two-thirds pineapple-juice and one-third bacardi, with a dash of grenadine” was cited in the book When It’s Cocktail Time in Cuba (1928) by Basil Wool. Fred Kaufman worked at the Hotel Sevilla, then called the Sevilla-Biltmore Hotel
 
The Mary Pickford Cocktail is sometimes credited to the bar at the Hotel Nacional de Cuba, but this hotel was built if 1930—after the cocktail already existed. Popular mixologist Eddie Woelke of Havana’s Jockey Club has been credited since 1955 for originating the drink, but it’s probable that the 1926 and 1928 citations crediting Fred Kaufman of the Sevilla-Biltmore Hotel are correct.
 
   
Wikipedia: Mary Pickford
Mary Pickford (April 8, 1892 – May 29, 1979) was a Canadian motion picture actress, co-founder of the film studio United Artists and one of the original 36 founders of the Academy of Motion Picture Arts and Sciences. Known as “America’s Sweetheart,” “Little Mary” and “The girl with the curls,” she was one of the Canadian pioneers in early Hollywood and a significant figure in the development of film acting.
 
Because her international fame was triggered by moving images, she is a watershed figure in the history of modern celebrity and, as one of silent film’s most important performers and producers, her contract demands were central to shaping the Hollywood industry. In consideration of her contributions to American cinema, the American Film Institute named Pickford 24th among the greatest female stars of all time.
   
The Wikitender: Mary Pickford
The Mary Pickford is a Mixed Drink which consists of Cuban Rum, Fresh Pineapple Juice, and Grenadine Syrup.
 
Who created the Mary Pickford?
The Mary Pickford was created by Fred Kaufman, at the Hotel Sevilla, Cuba. (1920’s)
 
Google Books
A Winter in Paradise
By Alan Parsons
London: A.M. Philpot
1926
Pg. 35:
We lunched with the Hicklings at the Sevilla, well, off red snapper and heart of palm salad, with a Mary Pickford cocktail.
 
Google Books
When It’s Cocktail Time in Cuba
By Basil Woon
New York, NY: Horace Liveright
1928
Pg. 40:
The two other cocktails mostly in demand in Havana are the president_ and the Mary Pickford. The presidente is made with half bacardi and half French vermouth, with a dash of either curacoa or grenadine.  It is the aristocrat of cocktails and is the one preferred by the better class of Cuban. The Mary Pickford, invented during a visit to Havana of the screen favorite by Fred Kaufman, is two-thirds pineapple-juice and one-third bacardi, with a dash of grenadine. Both cocktails are sweetish and should be well shaken. The pineapple juice must be fresh-squeezed.
 
26 January 1929, Havana: The Magazine of Cuba, “A Lesson in Cocktails,” pg. 45, col. 1:
The “Douglas Fairbanks” is similar to the “Ideal,” but the “Mary Pickford” is a swell pink ceremony in a slim glass, made of pineapple, Bacardi, orange juice and grenadine.
     
19 February 1929, Havana: The Magazine of Cuba, pg. 7, col. 1:
I prefer the “Mary Pickfords” at the Florida bar to those brewed at any other establishment I know of.
 
Google Books
Two Hundred Selected Drinks
By Knut W. Sundin
Göteberg: Ragnar Orstadius Boktryckeri
1930
Pg. 24:
Mary Pickford.
Fill the shaker half full of broken ice and add: 2/3 ot Bacardi Rum 1/3 ot Pineapple juice 2 dashes of Grenadine syrup. Shake well and strain into a cocktail glass.
 
Google Books
Movieland
By Ramón Gómez de la Serna
New York, NY: The Macaulay Co.
1930
Pg. 67:
“Waiter, a Mary Pickford cocktail.” This cocktail produces in one’s soul the same effect as the provoking grace of its namesake.
 
Cuban Cookery:
Gastronomic Secrets of the Tropics, with an Appendix on Cuban Drinks 
By Blanche Z. De Baralt
Havana: Editorial “Hermes”
1931
Pg. 122:
Mary Pickford Cocktail
 
5 September 1934, The Register (Sandusky, OH), “Screen Life in Hollywood” by Hubbard Keavy, pg. 9, col. 2:
The Mary Pickford cocktail, according to a match book, consists of Italian vermouth, peach brandy, gin (mostly) and lime juice.
 
Gourmet magazine
MARY PICKFORD COCKTAIL
MAY 1943
(...)
An old favorite with us. Take 2 ounces Gold Label rum, 1 ounce fresh pineapple juice, a dash of grenadine, and a dash of maraschino—these last to taste. Must be very cold to be good.
   
18 November 1955, The Era (Bradford, PA),  “On the Side” by E. V. Durling, pg. 12, col. 6:
THAT COCKTAIL…
Did Mary Pickford have a cocktail named in her honor? If so, what is the recipe? Such is the query of a Beverly Hills, Calif., barman. That distinguished mixologist, Eddie Woelke of the Jockey Club, Havana, Cuba, originate the Mary Pickford cocktail recipe of which is as follows: one and one half ounces of rum, three quarters ounce of French vermouth, three dashes of grenadine. Shake with ice. Strain into cocktail glass.
 
My Cuban Cocktail Recipe Book
By Ramon Pedreira Rodriguez
Havana: Editorial Arte y Literatura
First English-language edition: 1997
Second English-language edition: 2000
Pg. 69: 
Mary Pickford
(...)
Although this cocktail was named after the famous North American actress, it was created in Cuba.
   
Sloshed!
Mary Pickford Cocktail
February 14th, 2011
(...)
The cocktail named for Mary Pickford is variously attributed to a few different people, but the most likely creator is Eddie Woelke, who moved to Cuba during Prohibition and helmed the famed Jockey Bar in Havana. Though the Mary Pickford is not unknown, Woelke is better known as the creator of the El Presidente, a similarly rum-based tipple that has been enjoying a resurgence in popularity. The Mary Pickford is particularly interesting, as its composition is sort of proto-tiki, foreshadowing the tropical concoctions that would become all the rage in Hollywood (and elsewhere) after Prohibition.
 
2 oz gold rum (Cuban-style, if you have it)
1 oz fresh pineapple juice
dash grenadine
dash maraschino liqueur
 
Add all ingredients to a shaker filled with ice. Shake well, strain into a chilled cocktail glass and serve.
   
Vince Keenan
FRIDAY, MAY 04, 2012
Cocktail of the Week: The Mary Pickford
(...)
For my first stab at a more adventuresome rum drink I chose another born of Cuba. The Mary Pickford, crafted at Havana’s Jockey Club, was indeed named after the silent film legend, so how could I resist? There is no evidence, alas, that she ever sampled it.
(...)
The Mary Pickford
2 oz. rum
¾ oz. pineapple juice
½ oz. maraschino
¼ oz. grenadine
Shake. Strain. No garnish.
POSTED BY VINCE AT 11:06 AM  
 
The Rachel Maddow Show
October 4, 2013
Cocktail Moment: The Mary Pickford