Jennifer Aniston’s Awkward Late-Night Moment That Still Has Fans Talking

David Letterman has long been known as one of television’s most iconic late-night hosts — sharp, funny, and sometimes a little too bold. But as old clips resurface in the age of social media, not all of his moments with celebrity guests have stood the test of time. One interview that continues to spark discussion features Jennifer Aniston, who appeared on The Late Show in 2006 to promote her film The Break-Up.

What started as a friendly conversation quickly turned uncomfortable. Aniston, dressed in a simple black blouse and shorts, found herself on the receiving end of repeated comments about her legs instead of her new movie. Letterman complimented her “tremendous legs,” circling back to the topic several times despite her polite attempts to move on. Watching it now, the exchange feels awkward — a reflection of how much talk-show culture has changed over the years.

The conversation didn’t stop there. Letterman also pressed Aniston on her rumored relationship with co-star Vince Vaughn and asked about her role in the film’s more revealing scenes. Though visibly uneasy, she handled it all with her usual composure and humor, keeping the interview on track despite the tension.

This wasn’t the first time the two had shared an uncomfortable moment. Years earlier, a 1998 interview made headlines after Letterman unexpectedly pulled Aniston close and kissed a strand of her hair — a clip that continues to circulate online and draw criticism today.

Despite the awkward encounters, Aniston remained gracious. She returned to The Late Show several times afterward, often turning uncomfortable moments into lighthearted exchanges. Her professionalism and warmth never wavered, reminding viewers why she’s one of Hollywood’s most respected stars.

Looking back, these interviews highlight how much entertainment culture has evolved. What once passed as casual humor now opens important conversations about respect, boundaries, and how women in the spotlight are treated. Through it all, Jennifer Aniston’s calm and confident presence has remained the constant — a quiet reminder that grace can outshine even the most uncomfortable moments.