Trending badgeTrendingPosted 2 hours ago19 Of The Most Awkward Celeb Interviews Of All TimeFrom hilariously cringe to low-key devastating, these celeb interview moments are both hard to watch and impossible to look away from.by Jenna GuillaumeBuzzFeed ContributorFacebookPinterestLink I like to think I'm something of a celeb interview connoisseur, which basically means I've spent a considerable chunk of my one precious life watching them for hours on end on YouTube. So I'm well-versed in the many, many awkward celeb interview moments - here are some standouts... 1. When Cynthia Erivo and Ariana Grande held space (and fingers). Out / Via youtube.com When Out's Tracey E. Gilchrist interviewed Cynthia Erivo and Ariana Grande for the Wicked press tour and asked Cynthia how she felt about people "holding space" for the lyrics of "Defying Gravity", a truly baffling interaction ensued - and a beautiful meme was born. Watch the interview here: View this video on YouTube Out / Via youtube.com 2. When Dakota Johnson confronted Ellen. NBC / Via youtube.com What was possibly meant to be funny banter on The Ellen DeGeneres Show turned awkward (for Ellen - hilarious for the rest of us) when Dakota Johnson wouldn't let Ellen get away with claiming she wasn't invited to her birthday party - and then backed it up by basically saying Ellen was not her fave comedian. Watch the interview here: View this video on YouTube NBC / Via youtube.com 3. When Ellen tried to force Mariah Carey to announce her pregnancy. NBC / Via ET / youtube.com In 2008, Mariah Carey appeared on The Ellen DeGeneres show, and Ellen harassed her into drinking champagne to "prove" she wasn't pregnant. The moment is even worse in hindsight - Mariah later said she was pregnant, but wasn't ready to announce it, and she subsequently had a miscarriage. Watch the interview here: View this video on YouTube NBC / youtube.com 4. When Heath Ledger just wanted to eat his orange. Seven / Via youtube.com While promoting Lords of Dogtown, Heath Ledger (RIP 😢) was interviewed for the Australian morning show Sunrise, and spent the entire time focused on peeling and eating an orange. Heath later apologized and said he'd been tired, hungry, and dehydrated. Watch the interview here: View this video on YouTube Seven 5. When Barbara Walters was real weird about Dolly Parton. ABC / Via youtube.com Barbara Walters asked many, well, questionable questions during her time, but her 1978 interview with Dolly Parton is now infamous for a number of very rude questions about Dolly's class, looks, and personality. The only reason it's watchable at all is Dolly's complete charm, wit, and confidence in responding to Barbara. Watch the interview here: View this video on YouTube ABC / Via youtube.com 6. When an interviewer excluded Ayo Edebiri from a question about Me Too and Black Lives Matter. ArtsLife / Via youtube.com During the Venice Film Festival in 2025, Italian journalist Federica Polidoro interviewed Andrew Garfield, Julia Roberts, and Ayo Adebiri together, and directed a question about Me Too and Black Lives Matter being "done" just to Andrew Garfield and Julia Roberts. All three actors seemed taken aback, and Ayo gracefully but firmly interjected, saying "I don't know if it's purposeful that [the question is] not for me - I don't think it's done". Watch the interview here: View this video on YouTube ArtsLife / Via youtube.com 7. When Vin Diesel obsessed over an interviewer's looks. Carol Moreira / YouTube Vin Diesel's 2016 interview with YouTuber Carol Moreira got incredibly awkward when he repeatedly talked about her looks, calling her beautiful and sexy despite her trying to keep him on topic and being clearly uncomfortable. Watch the interview here: View this video on YouTube Carol Moreira / youtube.com / Via youtube.com 8. When Diane Sawyer made Britney Spears cry. ABC / Via Entertainment Tonight / youtube.com It's an understatement to say Britney Spears was going through a hard time in the 2000s - and honestly, it wasn't a secret even at the time. In 2003, Diane Sawyer interviewed the then-21-year-old and asked her a series of judgmental questions about her former relationship with Justin Timberlake, her sexual history, and her spending habits, amongst other things. A clearly uncomfortable Britney eventually broke down in tears and asked for the interview to be stopped. Watch the interview here: View this video on YouTube ABC / Via Entertainment Tonight / youtube.com 9. When David Letterman made Lindsay Lohan cry. CBS Back in 2013, Lindsay Lohan appeared on The David Letterman Show to promote Scary Movie 5, and instead of asking her about the movie, David Letterman questioned her about her addiction and impending rehab stay - seemingly without her consent. She played it off with some jokes but by the end of the interview she was actually in tears. Watch the interview here: View this video on YouTube CBS / Via youtube.com 10. When David Letterman sucked on Jennifer Aniston's