I was re-interviewing for the job I already had (going temp to contract for an administrative role) which was shitty enough, but I heard a rumour that one of the young men on the panel had a habit of asking applicants weird questions for fun, to try to make them uncomfortable. He asked a colleague of mine if she'd had enough sleep that night, that kind of thing. The other person on the interview panel was a very nice, very professional older lady.
Context - a few years prior, I'd helped to run a semi-famous adult store for a two years (running sales and helping manage the team, etc.). I'm not ashamed of any aspect of that job, so it's stated matter-of-factly on my CV. Part of the attraction of our store was live pole dancers every weekend.
Anyway, this dickhead interviewer saw this on my CV and thought he'd struck gold. At the end of my (very good and ultimately successful) interview, he asked "I noticed you worked at [Shop]. When you worked there, did you do... everything?". I was onto him, so I calmly rattled off a list of my regular duties, but he kept pressing "So, like... did you do EVERYTHING there?"
I let him push me for a minute, then replied with "Oh, you're asking me if I was a pole dancer!". You should have seen the older lady's face as she glared at him. I continued "No, but I helped manage our dance team at the weekends. SO YOU'VE BEEN TO OUR SEX SHOP, THEN? What did you think? Did you get anything while you were there?"
Amazing how many people have thought they could use my work history to embarrass me when I happily polished butt plugs in public for years.