Playboy Magazine’s most sought after cover of all time is undoubtedly their December 1954 inaugural issue featuring Marilyn Monroe. Their second most desired cover might arguably be the June 1959 issue, especially because three different types of fans truly love it: people who dig Italian motor scooters (that’s a Lambretta on the cover, not their rival, Vespa); fans of Jack Kerouac, as his name and article “The Origins of The Beat Generation” appear on the cover; and lastly, admirers of Jackie Kennedy Onassis will note the distinctly Jackie O look-alike aboard the scooter.
In the zeitgeist of 1959, both Jackie Kennedy and Jack Kerouac were all the rage when it came to the intersection of culture and cool. Jackie was much more famous than Jack, of course. Her husband, the junior Senator from Massachusetts, had already been considered a possible Vice President by the Democrats in 1956, and in October 1958, Frank Sinatra came out in support of a Kennedy presidential campaign. The intersection of culture and cool came together around October 1, 1959 as represented in the black-and-white photograph below.
Even though JFK wouldn’t formally announce he was running for president until January 2, 1960, it was obvious he had been thinking about it for a very long time. His 1955 bestseller Profiles in Courage is a classic among books written by politicians to elevate their political ambitions. Then in September of 1959, his father, Joseph P. Kennedy, bought him a private jet that would turn out to be the very first private plane used in a presidential campaign.
The plane was called the Caroline, named after the couple’s only child at the time. It was a 1948 Convair 240 (2 engines, 40 passengers) purchased used from American Airlines for $385,000 (about $3.5M today). The plane was nicknamed “The Mother Ship,” and the Kennedys took delivery on October 1, 1959.
What else happened on October 1, 1959? That was also the publication date for the paperback edition of Jack Kerouac’s novel The Dharma Bums, his second most popular book—which Jackie can clearly be seen reading while onboard the airplane. In other photographs JFK can be seen sitting in his seat eating clam chowder (and maybe discussing yabyum?)
In 1967, the Caroline was donated to the Smithsonian Institution’s Air and Space Museum, in a ceremony presided over by the President’s brother, Robert F. Kennedy.