Jennifer Aniston — David Letterman
In the annals of cringe-worthy interview moments, one between Jennifer Aniston and David Letterman during an episode of The Late Show in 1998 stands out as particularly bizarre and uncomfortable. As the conversation unfolded, it took an abrupt and unsettling turn when David Letterman, seemingly out of the blue, scooted closer to Jennifer Aniston and remarked that he "just want[ed] to try one thing." What followed was a moment of sheer weirdness as he held her head in place and placed a strand of her hair in his mouth. Jennifer, understandably bewildered and uncomfortable, tried to pull away while attempting to laugh off the inexplicable situation.
To make matters even more cringe-inducing, David Letterman repeated the strange hair-eating act, leaving Aniston and the audience stunned and perplexed. To cap it off, he casually handed her a napkin to wipe her hair off as though nothing extraordinary had happened. This bizarre episode left a lasting impression on viewers and has since become emblematic of the awkwardness that can sometimes occur in celebrity interviews.
