Not me, but once at school the headteacher covered one of our lessons and clearly couldn’t be arsed to do anything proper, so we just had a relaxed half hour. Then he asked a bunch of people to tell him their best joke. Everyone sensibly went for the least offensive joke in their (13 year old boys) repertoire, which were all very safe and unfunny. Then Tom Barry completely froze and went for:
Why did Princess Diana cross the road?
Because she wasn’t wearing a seatbelt.
audible inhalation through the room, so painful