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In the realm of celebrity interviews, certain moments stand out for their sheer awkwardness, eliciting both amusement and discomfort from audiences. From unexpected questions to uncomfortable silences, these instances illustrate how the spotlight can foster some truly cringeworthy interactions. Here are the facts: we explore some of the most unforgettable and awkward celebrity interview moments that have made headlines.
The facts
One particularly bizarre exchange occurred during a promotional interview for the musical Wicked, where Cynthia Erivo and Ariana Grande were caught off guard by a question about the lyrics of “Defying Gravity.” This unexpected query led to a moment that quickly became a viral meme, showcasing how some interactions can spiral into confusion.
When fun turns into discomfort
On The Ellen DeGeneres Show, Ellen faced an awkward moment when actress Dakota Johnson confronted her about a birthday invitation. The playful banter shifted as Dakota asserted that Ellen was not her favorite comedian, leaving the audience in stitches while Ellen appeared visibly flustered.
Another eyebrow-raising instance occurred during a 2008 episode featuring Mariah Carey. Ellen pressured Carey to drink champagne to dispel pregnancy rumors, an act criticized when Mariah later revealed her actual pregnancy and subsequent miscarriage. This moment serves as a poignant reminder of the sensitivity surrounding personal topics.
The consequences
The late Heath Ledger was once interviewed on an Australian morning show during the promotion of Lords of Dogtown. Instead of engaging with the conversation, he became preoccupied with peeling an orange. His later apology revealed he was simply tired and dehydrated, highlighting how personal circumstances can influence an interview.
During the 2025 Venice Film Festival, a journalist directed an inappropriate question regarding social movements like Me Too and Black Lives Matter to Andrew Garfield and Julia Roberts. Ayo Adebiri stepped in gracefully, asserting that the topics were still relevant and emphasizing the importance of inclusivity in discussions that matter.
Meanwhile, Vin Diesel‘s interview with YouTuber Carol Moreira took a different turn when he repeatedly complimented her appearance, making her visibly uncomfortable while she attempted to steer the conversation back to the subject matter. Such moments illustrate the challenges of maintaining professionalism in the entertainment industry.
Emotional turmoil on camera
In 2003, a young Britney Spears faced a tough interview with Diane Sawyer, who bombarded her with questions about her past relationships and personal choices. Britney’s discomfort culminated in tears, prompting her to request a halt to the interview, which starkly highlighted the pressures faced by celebrities and the emotional toll of public scrutiny.
Another notable incident occurred when Lindsay Lohan appeared on The David Letterman Show in 2013. Instead of discussing her film, David delved into her struggles with addiction, leaving Lindsay in tears by the end of their conversation. This showcases the fine line interviewers walk between professional curiosity and personal boundaries.
In a particularly strange exchange from 1998, David Letterman asked Jennifer Aniston a series of inappropriate questions before playfully sucking on her hair, an act that left her visibly startled and the audience in disbelief.
Handling unexpected situations
One particularly bizarre exchange occurred during a promotional interview for the musical Wicked, where Cynthia Erivo and Ariana Grande were caught off guard by a question about the lyrics of “Defying Gravity.” This unexpected query led to a moment that quickly became a viral meme, showcasing how some interactions can spiral into confusion.0
One particularly bizarre exchange occurred during a promotional interview for the musical Wicked, where Cynthia Erivo and Ariana Grande were caught off guard by a question about the lyrics of “Defying Gravity.” This unexpected query led to a moment that quickly became a viral meme, showcasing how some interactions can spiral into confusion.1
One particularly bizarre exchange occurred during a promotional interview for the musical Wicked, where Cynthia Erivo and Ariana Grande were caught off guard by a question about the lyrics of “Defying Gravity.” This unexpected query led to a moment that quickly became a viral meme, showcasing how some interactions can spiral into confusion.2