There’s something timeless about an uncomfortable interview. Whether it’s due to an incompetent interviewer, an annoyed artist, or illicit substances on either side, moments like these get shared and discussed for decades.

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KISS found themselves receiving backlash after an awkward encounter with a South American interviewer. The journalist wore an Iron Maiden shirt to his interview with the band, and before the chat even got started, Paul Stanley and Gene Simmons protested the man’s choice of apparel. Ultimately, Simmons pressured the interviewer into wearing a KISS shirt, creating an uncomfortable, high school bully dynamic.

Courtney Love’s ill-fated crossing of paths with Madonna at the 1995 MTV Video Music Awards has to be one of the most surreal moments in television history. No doubt struggling with substance abuse along with the death of her husband Kurt Cobain the previous year, Courtney Love interrupted a live interview with Madonna by throwing her compact over the pop star’s head.

Courtney ended up crashing the interview, chasing Madonna away as a visually annoyed Kurt Loder was forced to continue speaking with Love. The Hole frontwoman ended up face planting off her chair while claiming that she’d slept with Ted Nugent in the past.

Check out The Most Uncomfortable Interviews Ever in the Loud List below.

The Most Uncomfortable Interviews Ever

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