Frank Sinatra: High Hopes (1960)

When the handsome young John F Kennedy ran for the US presidency in 1960 (and beat Richard Nixon), there were planty of people weighing in with support.

And one of his biggest fans was Frank Sinatra who courted JFK and brought his high profile friends in the Rat Pack, as well as other Hollywood types, into the spotlight in support.

Sinatra also produced the inaugural ball for JFK.

But it all turned sour later when he invited JFK to visit him at his Palm Springs house. Sinatra had a helicopter landing pad built on extra land that he purchased and also had a new guest house constructed.

It is said that when JFK cancelled -- maybe on advice to distance himself from Sinatra and his Mob connections -- the singer took to the helicopter landing pad with a sledgehammer, such was his fury.

Their friendship never flourished in the way that Sintra had hoped, and within a short period he had shifted political allegiances . . . and became a Republican.

But back in 1960 when Kennedy was runing Sinatra was right there -- and even sang this as a fundraiser for the Kennedy campaign.

Want more oddities, one-offs or songs with an interesting backstory then check the daily updates at From the Vaults.