Give the People What They Want

In his book How to Be the Greatest Improvisor on Earth, Will Hines shares a story from his time in class. The scene was a simple gambling scene, with a couple playing roulette, letting their winning ride on the same number over and over again, winning each time:

The couple screamed! The class loved it. Then the teacher, Ali Farahnakian, edited the scene and said, "Kudos for the decision to make them keep winning. That's what I want. I come to improv shows hoping to be blown away." The lesson was clear. Top of your intelligence would say you can't win that many times in a row. But a good sense of theatrics and patterns says: yes, it can happen.

You can't just jump straight to such huge outcomes. You have to earn it step by step. You can't break reality, but you should, with good comedic taste, bend it.
- How to be the Greatest Improvisor on Earth pg. 68

When I was in rehab, a common event was to play Spades with illicit playing card decks that people managed to get access to. In the rehabs I went to, playing cards are officially banned since gambling is, rightfully, frowned upon. I believe this is common. Staff look the other way on this in the way that Col. Potter looked the other way on Hawkeye's gin still in MASH. Technically, a rules violation, but if it keeps people happy, maybe it's worth it. Most of the time, if there was a deck around it, it was because a staff member brought it in.

One evening, during a Spades game, I decided to head downstairs to get a cup of coffee, and I asked if anyone else in the room wanted anything. Someone asked for a cup of coffee, and then another person asked for coffee, and then it became a bit, and everyone, one by one, asked for a cup of coffee, all nine people. It was funny. I left. By the time I got downstairs, I realized that it would be even funnier if I actually got everyone a cup of coffee. So I did. I got ten cups, I assembly-lined them up with lids and sleeves, filled them up with coffee. Filled my pockets with cream and sugar packets. Then, I stacked the cups and carried all ten back up the stairs through the heavy doors to the community room. Let me tell you that me carrying a cartoon-stack of ten cups of coffee into the room absolutely killed.

Unless it is part of a game move, improvisers should resist trying to fulfill the audience's expectations, says George Wendt of Cheers; fortunately this is easier in improv than for performers trying to develop material further.
"Always assume the audience is one step ahead of you?" he says, quoting one of most useful rules he learned while working with Del.
In improv, you almost never give the audience what they're expecting, because you're working on the fly — this really relates more to shaping the material.
"Always assume that the audience is going to get the easy joke. In other words, if an audience sees a set-up coming, they're less likely to laugh at the joke. If they see a set-up coming, you'd better do a quick 180 and give them something that they don't expect," he says.

— Charna Halpern, Del Close, and Kim "Howard" Johnson, Truth in Comedy (pp. 44-45)

Sometimes the most surprising and hilarious thing you can do is exactly what people ask you.