The One Thing About Princess Diana That Billy Crystal Couldn't Help But Poke Fun At

Princess Diana, known for her widespread popularity and influence, left a lasting impression on many, including the celebrities she met throughout her life. However, there are still many things we learned about Princess Diana after her death, especially given the popularity of "The Crown" on Netflix. While most remember her for her humanitarian efforts, iconic public appearances, and her stunning transformation, others recall more personal moments, such as actor and comedian Billy Crystal. 

Even though she was royalty, Diana was also a well-known celebrity, both globally and in Hollywood. During an October 2024 appearance on "The View," Crystal joked about the time he met Diana at the 1989 London premiere of his famous rom-com "When Harry Met Sally" (via People). In this rare encounter, Crystal revealed that what stood out most wasn't just the princess' presence but her distinctive reaction to the film's most famous scene: Meg Ryan's "I'll have what she's having" restaurant moment. Also known as the scene that mortified Meg Ryan's kids. 

At the 1989 premiere of "When Harry Met Sally" in London, Billy Crystal was in the perfect position to observe Princess Diana. During his interview on "The View," Crystal recalled sitting with the then-Princess of Wales to his left and actress Meg Ryan seated further down. "So it's me, [director Rob Reiner], Princess [Diana] and then Meg," he said (via People). 

As the film played, the audience anticipated Diana's reaction to the now-iconic fake orgasm scene performed by Ryan. Crystal noted that the audience in the theater shifted their focus away from the screen, curious to see how the royal would respond to such a comedic and unexpected moment. "The whole audience below us is now looking back to see how the princess is going to react to Meg faking the orgasm," Crystal explained, describing the unusual situation of watching one of his raunchiest films with a member of the royal family. 

According to Crystal, the princess reacted with laughter, but the comedian went on to poke fun at the princess' reaction. "So she starts laughing — a big laugh," he said. He doubled down on his jokes by saying that her laugh was so distinctive that if they had been on a date, there would not have been a second one. "'Cause I'd go, 'The laugh. She's beautiful but the laugh!'" he remarked. Crystal finished the story by recalling the night as memorable and noting how much it meant to meet Diana, referring to the evening as "spectacular." At least now we know one of Crystal's dating dealbreakers: a big laugh.