In Hollywood, not every moment on the red carpet or in front of the camera is picture-perfect. While countless charming and captivating interviews exist, some stars are trapped in cringe-worthy moments that make us squirm.
From inappropriate questions to glaring identity mix-ups, these 10 interviews have one thing in common: they left the audience, and often the celebrities themselves, in sheer disbelief.
David Letterman’s Invasive Dig at Lindsay Lohan’s Rehab Plans
During a 2013 Late Show interview to promote Scary Movie 5, Lindsay Lohan was questioned by host David Letterman about her upcoming rehab visit. Letterman’s tone was immediately confrontational.
Despite complimenting Lohan on her appearance, Letterman relentlessly questioned her about alleged theft and financial management, causing her obvious discomfort. Lohan, visibly perturbed. She requested a shift to positive topics, emphasizing her desire to keep the discussion light and promotional, as intended.
Samuel L. Jackson Mistaken for Laurence Fishburne
During a live interview, news anchor Sam Rubin from KTLA made a mistake when he mentioned a Super Bowl commercial that Samuel L. Jackson had no involvement in. This caused an awkward and tense moment.
Jackson corrected Rubin, pointing out the irony and inappropriateness of the mistake, especially since Rubin is an entertainment reporter. Despite the uncomfortable situation, Jackson’s response was stern and corrective.
Megan Fox’s Revelations Met with Jimmy Kimmel’s Insensitivity
In a 2009 episode of Jimmy Kimmel Live!, Megan Fox shared her experience as a minor extra in Bad Boys II. The director, Michael Bay, had to work around her age by not allowing her to be shown with alcohol or at a bar.
Instead, she was asked to wear a stars-and-stripes bikini, a red cowboy hat, and six-inch heels to dance under a waterfall, which resulted in her getting wet. Kimmel responded dismissively, implying that many people shared Bay’s exploitative approach but chose not to reveal it.
An Unsettling Moment Between Jennifer Aniston and David Letterman
In a 1998 episode of The Late Show, Jennifer Aniston was in an unexpected and uncomfortable situation with host David Letterman. While discussing her aversion to flying, Letterman unexpectedly moved closer to Jennifer Aniston.
As a drumroll amplified the tension, he strangely placed his hand on her neck and attempted to suck a strand of her hair, leading a visibly shocked Jennifer Aniston to recoil and dry her hair with a napkin. Despite the evident discomfort of the moment, Letterman tried to lighten the mood by commenting on her reaction, to which Aniston admitted her trauma from the peculiar encounter, half-jokingly signaling for an exit.
Anne Hathaway’s Body Becomes the Focus
In 2012, while promoting her role as Catwoman in The Dark Knight Rises, Anne Hathaway faced an uncomfortable line of questioning from Extra reporter Jerry Penacoli, who seemed fixated on her physique.
Delving into her “feline fitness regime,” Penacoli emphasized the need for Hathaway to be in “perfect shape” for the film. Ever the professional, Hathaway clarified that her training was more about executing stunts and fights effectively than mere aesthetics.
Taylor Swift’s Unexpected Red Carpet Encounter
At the 2015 Grammy Awards, Taylor Swift faced a rather inappropriate comment from an Entertainment Tonight reporter while showcasing her attire on the red carpet. Swift allowed the camera to focus on her dress and shoes. The Entertainment Tonight interviewer suggested she could go home “with maybe more than just a trophy.”
“I just wanted to show the legs… you’re going to walk home with maybe more than just a trophy tonight. I think lots of men.”
Swift, known for her swift retorts, gracefully responded by stating she had no plans of walking home with any men. Instead, she intended to spend time with friends post-ceremony and head home to her cats.
Uma Thurman Faces Age-Related Questions from David Letterman
When Uma Thurman, then a 25-year-old actress fresh off her Pulp Fiction success, appeared on The Late Show, host David Letterman navigated the conversation into personal waters. Steering away from her professional accomplishments, he inquired about the age of the oldest man she’d ever dated.
When she responded negatively, Letterman further prodded about her short-lived marriage. Before moving on, he unexpectedly complimented Thurman’s ears, calling them “perfect,” only to wrap up the segment by making the entire exchange feel unsettlingly personal.
Vin Diesel’s Overbearing Flattery
In 2016, Brazilian YouTuber Carol Moreira interviewed actor Vin Diesel to discuss his illustrious career. However, the conversation took an unsettling turn as Diesel.
Mid-discussion about Saving Private Ryan, Diesel digressed to comment on her beauty, even addressing the offscreen crew about her looks. When Moreira attempted to redirect the conversation by mentioning their shared interest in Dungeons and Dragons, Diesel persisted with his flirtatious advances.
Rashida Jones’ Tan Becomes a Topic of Discussion
At the 2015 Screen Actors Guild Awards, as cameras appreciated Rashida Jones’ stunning gown, a reporter’s comment about her tan took an awkward turn. Observing Jones’ complexion, the reporter remarked she seemed as if she had “just come off an island,” further describing her as “very tropical.”
In a composed manner, Jones gave a straightforward acknowledgment of her biracial heritage, with a Black father and white mother.
Ben Affleck’s Questionable Antics with Anne-Marie Losique
In 2004, Ben Affleck’s interaction with Anne-Marie Losique during a Box Office interview for Jersey Girl attracted attention due to Losique sitting on his lap and Affleck making questionable comments.
On the other hand, Losique had a different opinion about the situation. She explained to Entertainment Tonight that the way she interacted with Affleck was not what it seemed and was taken out of context.
