Late-night television has often reflected the cultural norms of its time, and revisiting older interviews sometimes reveals how those standards have changed. David Letterman, long known for his sharp humor and unpredictable style on The Late Show with David Letterman, is now part of a renewed discussion as some past interviews are viewed differently by modern audiences.

One of the most talked-about appearances involved Jennifer Aniston in 2006 while promoting the film The Break-Up. Much of the segment focused on comments about her appearance rather than her work, with repeated attention directed toward her legs and personal life, creating a moment that many viewers today see as uncomfortable.

An earlier 1998 interview resurfaced online as well, when Letterman unexpectedly placed a strand of Aniston’s hair in his mouth during the conversation. Although the audience laughed at the time, the moment has since been widely reexamined as an example of how personal boundaries for female guests were sometimes overlooked in entertainment.

Despite those awkward moments, Aniston handled the situations with composure and continued appearing on the show. During a later visit promoting Marley & Me, she shifted the tone by humorously presenting Letterman with a tie she had worn on a GQ cover, demonstrating her ability to redirect the conversation and maintain control of the moment.