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Seventy-seven years ago, during Prohibition, cousins Jack Kriendler and Charlie Berns opened the doors of Jack and Charlie's 21, named for its address on 52nd St. Frequent raids didn't shut the place down, nor did the repeal of the 18th Amendment in 1933. Instead, the bar, now dubbed the '21' Club, kept the Manhattans pouring for decades of boldface names, whether they’d made their names sculling on the St. Charles River, grimacing on the silver screen or keeping banker's hours on Wall Street. The now mostly vintage crowd downs its martinis and '21' burgers (which were Harvard-tuition expensive long before Daniel Boulud got into the act) in the main lounge, a stately den of tan leather armchairs and plush striped banquettes. For a taste of an era now nearly forgotten, little comes closer than a classic cocktail served by one of these gracious tuxedoed headwaiters in the Bar Room where old toy cars and airplanes drip from the ceiling like so many memories. — Amy Powell

Southside: a rum and mint cocktail invented here.