In 1953, Marilyn Monroe hesitated about appearing on The Jack Benny Program. The popular variety show aired live, so anything could happen. But her perfect performance in a skit where Jack Benny falls asleep on a cruise ship and finds himself alone on deck with the Gentleman Prefer Blondes star went off without a hitch and made the episode a ratings winner.

Marilyn’s time on the show cemented the two performers’ affection and respect for each other — a connection that would last until the end of her life. “Jack always loved women, and he had many female friends,” notes Kathryn H. Fuller-Seeley, author of Jack Benny and the Golden Age of American Radio Comedy. “He really credited women for their intelligence, personalities and as people, as opposed to other guys who saw women only as stereotypes and sex objects. He was often more comfortable with women than with men.”

In a business filled with men looking to take advantage of beautiful young women, Jack treated Marilyn with appreciation and courtesy. “Sometimes you go on somebody else’s show and they’d make mean jokes, or it might be kind of awkward or humiliating, but Jack always did right by his famous guest stars,” says Fuller-Seeley. “I’m sure Marilyn would have been nervous, but Jack had an incredible ability to make anyone feel comfortable.”

Inside Marilyn Monroe’s Unforgettable Performance

Marilyn’s appearance on Jack’s show would be her biggest live-television performance of the 1950s. The comedy they created together is still as funny now as it was then. “The wonder of that scene is her saying she can’t trust herself around him because she’s so incredibly attracted to him,” says Fuller-Seeley. “It’s delightful.”