A quick heads-up before diving into the story: I've set aside for you a complete shopping list of every ingredient you'll need so you can recreate this classic at home. Here's the tale.
The Mary Pickford is a piece of Cuban film history, created in Havana in 1922 by bartender Fred Kaufman at the Hotel Nacional, for a visit by the silent film star Mary Pickford, at the time "America's Sweetheart" and one of the co-founders of United Artists. Pickford had traveled to Cuba with her husband Douglas Fairbanks and the director Charlie Chaplin during the Prohibition years.
The cocktail, based on white rum, pineapple juice, grenadine and maraschino, has the same rosy color as Pickford's iconic "golden curls," and became one of the most ordered drinks in the Cuba of the Roaring Twenties. Today, visiting the Hotel Nacional, you can sit in the garden and order a Mary Pickford at the same bar where the godmothers of Old Hollywood sat.
To recreate this one with the right style, tools matter as much as the recipe. I use and recommend a complete barman kit like this set on Amazon, which covers every essential tool at a very reasonable price. For a more serious setup, a professional cocktail bar station keeps bottles, glasses and tools organized and close at hand, instantly upgrading the whole experience.