The Most Cringeworthy Late Show with David Letterman Interviews

The legendary Late Show with David Letterman has its share of memorable moments, but some interviews are notably unforgettable for all the wrong reasons. Let's take a look at three such cringeworthy experiences from the show's rich history.

Nastassja Kinski: A Bizarre Hairdo Gone Wrong

One of the earliest and most memorable cringe-worthy interviews took place during the NBC era, when Nastassja Kinski appeared on the show with a bizarre hairdo that looked as Dave Letterman later described it, 'wired up like a barn owl.' This dramatic hair style quickly set the tone for a disastrous interview.

Initial attempts to make light of the situation were futile since the hairdo was part of an elaborate gag. The conversation quickly descended into what Dave Letterman later referred to as one of his worst moments on the show. The interview was compounded by the fact that this was the only appearance that night, with the second guest, actors John Candy, almost doubling as the comedic relief during the interview by getting his hair styled to resemble Kinski's.

The Joaquin Phoenix Gum Incident

Joaquin Phoenix's interview with David Letterman stands out as another cringeworthy moment. During the conversation, Dave made a joke, saying, 'I'll come to your house and chew gum.' Playing along, Joaquin produced a pack of gum and stuck it under the desk, leaving them both in an awkward silence. It was only after Phoenix left the interview that Dave expressed his regret for the situation, saying, 'Joaquin, I'm sorry you couldn't be here tonight.' This incident serves as a poignant reminder of the consequences of living in the moment and taking the interviewer's jokes too literally.

Lessons from Cringeworthy Interviews

These cringeworthy moments in the history of the Late Show with David Letterman highlight the importance of preparation and flexibility in television interviews. Actors, comedians, and guests must be ready for unexpected challenges, especially when dealing with a person as charismatic and unpredictable as Dave Letterman. These interviews also demonstrate the power of humor and the ability to turn a negative situation into a comedic one, even with the most uncomfortable of guests.

The legendary David Letterman was a masterful interviewer who knew how to handle even the most uncomfortable situations. His intuition and wit were key components in turning potentially cringeworthy moments into entertaining and memorable experiences for the audience.

While these cringe-worthy interviews may not be the most memorable parts of the show, they add an extra layer of color and depth to the story of the Late Show with David Letterman that fans and critics can still point to and laugh about today.