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For the sake of that, I compiled five disastrous interviews with musicians. Thankfully, none of them were done by anyone on the SOTC staff.
How Not To Interview Musicians
5. Tom Waits
Tom Waits has given some bizarre interviews, including one which briefly became internet famous due to Waits' resemblance to Heath Ledger's portrayal of the Joker in The Dark Knight. Credit where it's due. though, interviewer Don Lane was a professional the whole way through.
The disaster here, then, was when Waits decided to promote his last record Bad as Me with an appearance on Late Night with Jimmy Fallon. The future Tonight Show host Fallon has done well for himself in the Late Night seat, but he showed his youth in conducting interviews in this one where he practically breaks down because he's so starstruck interviewing Waits. Waits plays it off decently, guiding Fallon through it, but it's clear how ridiculously nervous Fallon is to be in his presence and it ends up being terribly uncomfortable.
4. Billy Bob Thornton
Whatever you do, don't refer to Billy Bob Thornton as an actor when he's doing an interview as a musician. Billy Bob Thornton is a serious musician with a serious band, and you will not mention his other career.
The Q radio show on CBC found that out the hard way when Thornton's band the Boxmasters appeared and host Jian Ghomeshi briefly referred to Thornton's acting career in his introduction of the band. Apparently Thornton had instructed them not to bring that up and after it is mentioned, he refuses to answer questions until he finally simply blows up and has a fit over the whole thing.
Before Madonna even steps through the curtain, our host David Letterman assures bandleader Paul Shaffer that "everything is fine." But, of course, it's not, or this classic interview disaster wouldn't have made our list.
Everything goes horribly wrong after Madonna does come out and immediately goes on the attack, bringing Letterman a pair of her panties, then taking him to task for being so interested in her sex life. It's all downhill from there, especially when she starts cursing and referencing drugs. The best part is when she randomly starts giving Letterman tips on how to cure athlete's foot with your own urine.
See also: Famous Musicians Talk About Each Other, In Illustrated Form