I Showed Up to Work Soaked After Saving a Drowning Puppy – My Boss Told Me to Get Lost, Then a Man Stepped in Front of Me

David Letterman built much of his reputation on sharp comedy and unpredictable interviews, but time has changed the way many of those moments are viewed. A clip that repeatedly resurfaces is Jennifer Aniston’s 2006 appearance on The Late Show—an interview that already felt awkward years ago and feels even more uncomfortable now.

Aniston was there to promote her film The Break-Up. She walked onstage looking relaxed, dressed in a simple black blouse and tailored shorts. The conversation started normally, but almost immediately shifted when Letterman focused on her appearance, especially her legs. He complimented her outfit, then made several comments about her “tremendous legs,” circling back to the topic even when she tried to redirect the conversation toward the film. She smiled politely, the way many guests did, but the discomfort was clear.

The interview continued to drift into personal territory. When the topic of Vince Vaughn came up, Letterman joked about whether Vaughn encouraged her to appear nude in the film, catching her off guard. She deflected carefully, trying to steer the conversation back to safer ground. Later, Letterman commented on a camera shot he “couldn’t stop looking at,” leaving viewers to interpret the moment on their own. Aniston kept her composure, but it was difficult to watch even then.

And this wasn’t the only uncomfortable exchange between them. A 1998 clip frequently goes viral because of a particularly strange moment: Letterman pulled Aniston toward him, took a strand of her hair, and put it in his mouth. Aniston looked shocked and uneasy, and the moment still sparks disbelief whenever it resurfaces online.

Social media has repeatedly brought these clips back into the spotlight. One viral tweet in 2021 questioned how such moments were ever considered humorous. Viewed today, the exchanges feel less like light late-night banter and more like examples of how women in Hollywood were often placed in uncomfortable situations on national television.

Despite this, Aniston continued appearing on the show. She always responded with grace, choosing to smile, redirect, or joke her way through tense or awkward moments. Her professionalism became part of her public image, and she never criticized Letterman publicly. That wasn’t something many actresses felt free to do at the time, especially when promoting major films.

When she returned in 2008 to promote Marley & Me, she brought Letterman a playful gift—a necktie similar to the one she wore on a well-known magazine cover. Letterman laughed, swapped ties, and the moment felt lighter. But even then, the pattern of focusing on appearance or innuendo remained present.

Looking back, these interviews reflect a broader pattern seen across early 2000s media. Many actresses—among them Anne Hathaway, Lindsay Lohan, Britney Spears, and Paris Hilton—had to navigate uncomfortable questions and jokes during televised interviews. The tone that once went unquestioned is now widely discussed and reassessed.

What stands out most today is the way Aniston handled it all. She remained composed, thoughtful, and kind, even in situations that would now be called out immediately. Her reactions weren’t just polite—they were resilient. She navigated a demanding, judgmental industry with steady professionalism.

The interviews may not have aged well, but Aniston’s presence has. Her responses, her dignity, and her patience continue to stand out. In many ways, the resurfacing of these clips serves less to revisit the humor and more to highlight how much has changed—and how much she endured with remarkable poise.