So yesterday I was treated to a very Southwest-like situation with an AA captain who thought he was funny. It started at the boarding area, when the crew first entered to walk onto the plane. The captain says aloud, "This is the quietest boarding area I've ever seen." A few smiles, but no one really reacted.
Skip ahead, and we're now on the plane and the boarding is almost complete.
He walks out of the cockpit, to the main door and uses the FA's public address mic. He says, "Hi, I'm here to advertise for mandatory retirement ages for flight attendants." He was making a joke that the FAs were all a bit older, and teasing that they should be forced to retire. I didn't find it funny at all, bordering on sexism/ageism.
He then said, "Is everyone ready to leave?" No one really replied, so he said, "Well, we can stay here if no one wants to leave."
At this point, with the final passengers boarding, I'm wondering why he isn't in the cockpit running safety checks or something. I was in coach, and I could see the folks in J weren't finding his routine funny.

We took off early, but landed 20 minutes late. At the scheduled arrival time, he came on and said, "We are running 20 minutes late. But the good news is that we don't charge you any extra for the extra time you get to fly with us." NO ONE was please to hear that.