After finishing a set as atrium pianist on a cruise ship, I was about to walk up the staircase, which was spiral and majestic, when a passenger approached me and said "Awesome stairway." So I looked at the staircase and nodded my agreement, whereupon the passenger said "No, Stairway to Heaven," which I had just played. I thanked him.
At one point during a gig the guitarist invited one of his young students up to jam on a blues. They're nearing the end of a chorus, and the kid doesn't know where he is. I say "turnaround", to which the young student complies, doing a complete 360, coming around and facing front again with a baffled look on his face.
I believe they covered that in his next lesson.
As a vocal jazz quintet, we were used to playing all of the top venues in town. One of them was THE jazz club in town, and we played it frequently. The stage was set up to where one side of it was actually a bar where jazz fans could get closer to the artists, so it was always occupied by four or five patrons-of-the-arts.
One night, we finished a set with a song that ended abruptly. In the instant following the song, which would have normally been silent, we instead heard: "Don't tell ME - I've been to other planets and I KNOW!"
We did a trio gig (sax, bass, drums) backing a burlesque revue and had a sub drummer for the week. Since the dance routines changed weekly and were heavily choreographed, we got together with the dancers and our sub drummer for a rehearsal for that week's run of shows.
The guy we got was pretty overqualified but open to do it for the fun of it, and the choreographer/lead dancer was a young lady who was quite full of herself. She had no understanding of music and would make ridiculous musical requests, and made life generally miserable for a lot of the other people involved. It was evident that she was an amateur, as she had little to no formal dance training and disappointingly little natural ability.
We all got a bunch of satisfaction out of this exchange, which took place immediately after another of her inane musical 'directions' ---
Dancer: Have you ever even worked with dancers before?
Drummer: Sure I have.
Dancer (incredulously): Oh really? Where?
Drummer (nonchalant): Academy Awards.
She learned the lesson that we all take to heart as working musicians -- be humble, because you never know who you're talking to.
We were playing a Mall Christmas gig and the bass player's 90+ year old mother-in-law turned up to listen. This was a treat for her as she didn't get out much, and Pat, the bass player, was a great singer. He was, however, also known for rambling intros to songs and saying the right thing in the wrong way ... On this day he dedicated a song to his mother-in-law.
Unfortunately, he chose the song "Knockin' On Heaven's Door"
1976. A phone call from a drummer who is on the road with a national act.
Friend: Could you wire me some money?
Me: Sure. Where are you?
Me: Is that Washington State or Washington D.C. ?
Friend: Hold on, I'll go find out.
The lead singer of a band is handed a note by the club owner, and proceeds to announce on the mic:
"License plate ***-***, your car's been hit. That sucks. Does anyone here own that car?"
"Anyone? Again, the license plate is ***-***."
We then hear his girlfriend and fellow singer shout "Baby! That's our car!"
Ladies and gentlemen, we're gonna take a short break..."