Harry Caray did things like this all the time but the best one was during a break in the game. They were showing the crowd and the camera stopped on a young couple kissing.
Harry said something like, “ahhh young love at the ball park. He kisses her on the strikes and she kisses him on the balls.” :eek:
The other guy didn’t say anything for like 5 minutes. I think he fell off his chair laughing but old Harry just kept going like nothing happened.
Curse you Grant! That’s what I was coming in here to post! feh:)
But to mitigate Harry’s rep, he remembered my anniversary back when I was married and working at Wrigley Field and he and his wife sat down to a wonderful meal with us at his restaurant.
I had made a off hand joke about him saving me a couple nice pork chops about 5 weeks before the date. A couple days before, he asked me "so you still coming for your anniversary? I stammered “yes” and he told us he’d have a bottle of wine for us. We got there and not only was there a bottle, it was sitting at the table with him and his wife where we proceeded to sit for about 2-1/2 hours and talk and eat like GODS 
Then there was the time I got drunk with Turk Wendell at Murphy’s Bleachers and ended up playing lacrosse with him in the outfield at 2am…good times, good times.