Presenting the Congressional Gold Medal to Bob Hope in September 1963, President John F. Kennedy noted that he had attended the comedian’s USO show on Wendy Island in the South Pacific during World War II. “He was a gay, carefree young man,” Hope quipped in reply, “All he had to worry about was the enemy.” Hope later wrote, “What set Kennedy apart from all other presidents was his ability to genuinely laugh at himself. He opened the floodgates for presidential humor, the likes of which had never been seen before.”

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