iSteve commeter jimmyriddle came up with a nifty set of minimal handshake links from Napoleon Bonaparte, who lived from 1769-1821, to a living celebrity:
On Elba in 1814, the exiled Emperor had a 90 minute meeting with the future British prime minister John Russell (1792-1878). In the mid-1870s, the ex-Prime Minister helped raise his toddler grandson Bertrand Russell (1872-1970). In the mid-1960s, Bertrand Russell convinced Paul McCartney (1942 – ) to oppose the Vietnam War at Russell’s house in Chelsea in London.
Bertrand Russell would be my guess for the man who shook hands with more interesting people across a longer expanse of time than anybody else in history, due to his broad interests, ranging from math to popular journalism, and aristocratic social standing. Even as a nonagenarian, he was a major figure in the celebrity culture of Swinging Sixties London, when it was the coolest city in the world. But 50 years before meeting McCartney, Russell was meeting the likes of Ramanujan and Wittgenstein.
iSteve commenter Jonathan Mason adds: Bertrand Russell must be one of the few men who met both Lenin and McCartney.
Did anybody meet both Karl and Groucho Marx?