A clip from a 2006 interview between David Letterman and Jennifer Aniston has recently resurfaced, sparking fresh conversation about what many viewers now see as a deeply uncomfortable exchange. The actress appeared on “The Late Show” to promote her film “The Break-Up,” but the conversation quickly veered away from her work and toward her physical appearance. From the moment she sat down, Letterman fixated on Aniston’s legs, repeatedly complimenting them in a manner that left the actress visibly flustered and attempting to deflect the attention with nervous laughter.
Aniston, dressed in a chic outfit of a black blouse and shorts, found herself the subject of relentless praise for her choice of attire. Letterman declared her outfit “tremendous” solely because it showcased what he called her “fantastic legs.” He elaborated that such an outfit could only be worn by someone with “lovely, well-shaped, muscular, lengthy legs,” putting the actress in an awkward position where her professional appearance was being reduced to a single physical attribute. Aniston tried to downplay the moment, explaining she had simply dressed for the warm weather.
The host, however, was not ready to move on. Throughout the interview, he circled back to the subject, stating he “couldn’t get over” her legs. In a particularly uncomfortable remark, he expressed hope that someone was recording the show so he could continue “looking at this shot,” a comment that seemed to reference the camera’s frequent focus on her lower body. This persistent focus created a cringe-worthy atmosphere that has not aged well with modern audiences, who now view the exchange through a lens of professionalism and respect.
The leg comments were not the only source of discomfort. Letterman also pressed Aniston on her rumored relationship with co-star Vince Vaughn and posed an invasive question about whether it was Vaughn’s idea for her to appear naked in the film. Aniston handled the query with remarkable grace, deftly deflecting by suggesting Letterman should have asked Vaughn himself when he was a guest on the show. This combination of personal probing and physical fixation made for a challenging interview that tested the actress’s famed composure.
This was not an isolated incident in their history. In a notorious 1998 appearance, Letterman had physically grabbed Aniston’s neck and sucked on a strand of her hair, an act that left her visibly uneasy. Despite these awkward encounters, Aniston demonstrated professionalism by returning to the show in later years. The resurfacing of these clips has ignited a broader discussion about the treatment of women in entertainment during that era and how humor and interviewing tactics once considered acceptable are now being rightfully reevaluated.
