For years, David Letterman was considered untouchable in late-night television — quick-witted, unpredictable, and endlessly entertaining. But some interviews that once passed as harmless comedy are now being viewed through a very different lens.

One resurfaced moment involving Jennifer Aniston has sparked renewed conversation online, with many viewers saying the interview feels far more uncomfortable today than it did at the time.

The 2006 appearance on Late Show with David Letterman was supposed to promote Aniston’s film The Break-Up. Instead, the conversation quickly shifted toward her appearance — specifically her legs. Almost immediately, David Letterman repeatedly commented on them while the cameras awkwardly zoomed in.

“You have tremendous legs,” he told her more than once, refusing to let the topic go even as Aniston laughed nervously and tried steering the interview elsewhere.

Watching the clip today, many people notice what audiences often overlooked back then: her visible discomfort.

And it wasn’t an isolated moment. Older interviews have resurfaced as well, including a now-infamous 1998 appearance where Letterman unexpectedly grabbed a strand of her hair and placed it in his mouth while she sat frozen in surprise.

At the time, moments like these were often dismissed as “just late-night humor.” Today, they spark bigger conversations about celebrity culture, power dynamics, and how women in Hollywood were expected to smile through uncomfortable situations in public.

What stands out most now isn’t the joke itself.

It’s how gracefully Jennifer Aniston handled moments she likely should never have had to navigate in the first place.