15 Most Awkward Interviews Ever


From drunken on-air tomfoolery to aggressive political debates, we count 15 of the most uncomfortable celebrity interviews of all time!


15 – Ernie Dingo vs. Kyle Sandilands,


  • In 2008, an Australian radio interview degenerated into toxic name-calling. The interview, which took place between TV personality Ernie Dingo and 2DAY.FM host Kyle Sandilands, was to promote Dingo’s new show, Outback Wildlife Rescue. However, it was apparent that Dingo was on the back foot from the start and things quickly turned personal.
  • Sandilands doesn’t have the best reputation, and it certainly seemed like Dingo had preconceptions about him going in. It’s likely the interview was a contractual obligation.
  • Dingo’s contempt for Sandilands is revealed when he calls him a ‘commercial wanker’. He goes on to say that Sandilands is ‘over the top’ and suggests that he doesn’t care about animals.
  • Sandilands matches Dingo tit-for-tat and, in typical shock-jock fashion, avoids the highroad, squeezing in a final scathing remark before shutting the interview down. ‘What a cockhead you turned out to be, Ernie.’

14 – Kristen Stewart on Letterman,


  • In 2010, Kristen Stewart appeared on The Late Show with David Letterman to promote the third Twilight film, Eclipse.
  • Stewart is not a natural interviewee and, after a few rookie mistakes, unwittingly becomes Letterman’s plaything. You can see her growing more and more uncomfortable as the audience feasts on her accidental double entendres.
  • Letterman, exposing a bit of a cruel streak, subtly mocks Twilight, then foists a weird angry-dad lecture on Stewart after she confesses to owning a pet wolf. He actually lectures her about how farmers lose livestock to wolves, and Stewart is just sorta like, ‘Um, yeah, okay. That sucks. I still love my wolf, though.’ Uncomfortable viewing.

13 – Bruce Willis vs. Magic 105.4,


  • Yippee ki-yay! Don’t look now, but it seems the enemy planted a bug up action star Bruce Willis’s arse during his promotional radio interview for Red 2.
  • Right from the start, Willis is entirely disinterested in reporter Jamie Edwards’ questions. ‘This part is not acting,’ Willis sulks. ‘The fun part is over. We’re just selling the film now. Sales.’ Edwards goes on to ask him how he’d sell the movie to him. ‘I wouldn’t,’ says Willis. ‘I’d slash my hooves.’ You heard it here first, guys! Bruce Willis is part bovine!
  • Trying a different tact, Edwards quotes a line from the movie about the secret to keeping women happy, then asks if it’s proven true in Willis’s experience. Willis’ deadpan reply: ‘No. That’s just a line in a movie.’
  • In a last ditch effort, Edwards asks Willis if he enjoyed the film’s car chase scenes and receives this warm, fuzzy response: ‘I’m thinking about driving right now. I can hardly keep my mind on this interview. I’m thinking about driving up the M1. You have some great questions here, Jamie. Great chat.’

12 – Mark Wahlberg on The Graham Norton Show,


  • In 2013, ‘Marky Mark’ Wahlberg appeared on British talk show Graham Norton to promote his latest film Broken City. Norton and producers got a little more than they bargained for, though, when Wahlberg overindulged on the on-set wine.
  • Midway into the show, Wahlberg completed his seamless transformation into his jollier, drunken alter-ego. Drunken Mark Wahlberg’s hilarious antics included upstaging everyone, playing with the host’s nipples, and aggressively flirting with comedian Sarah Silverman while married.
  • Wahlberg went arguably too far during the show’s signature closing skit, the red chair. He flipped the chair lever three times before the audience member could get even the beginnings of her story out. Talk show whiplash at its best.

11 – Madonna on Letterman,


  • On March 31st 1994, Madonna’s appearance on the David Letterman Show became one of the most infamous television interviews in history. Letterman inadvertently sets the interview’s course when he refers to Madonna’s sex life during his introduction and then badgers her about kissing a stranger in the audience.
  • ‘The way he introduced me was derogatory,’ Madonna said, ‘so my whole thing was, okay, if that’s how you want to play it, you cannot beat me at this game.’
  • Madonna made Letterman squirm with her provocative and suggestive behaviour, and by requesting he smell her underwear. She used language that would make Mother Teresa blush (including fourteen f-bombs) and refused to leave the stage.
  • The episode received numerous complaints and was the most censored show in American talk-show history.


  • Epic (40%)
  • Wat (40%)
  • Lewd (20%)
  • No (0%)
  • Creepy (0%)