- Joe's speech to an unconscious Jimmy James when Jimmy had a heart attack was surprisingly poignant. Rare because Joe was often Out of Focus.
- For this troper, Jimmy's speech to Dave in "Station Sale" after he passes on the offer to sell counts as a Crowning Moment of Heartwarming (even though Dave had to pay him $7 for it):
Jimmy: These people... they're not employees. They're like family. And I can't imagine anything worse than having to part with them.
- Becomes a Crowning Moment of Funny as well when he immediately steps back into his businessman persona afterward and thanks Dave for the money. "I'm on a roll, I can't lose!"
- Really, Jimmy in general. It's rare to see a total spaz of a boss who is so attached to his employees. Once he broke off an engagement to a woman because she pulled him aside to inform him she thought they were weird.
- In one episode, Jimmy has a coma-inducing heart attack. When Dave and Lisa come to visit him, and a doctor mentions that he has a big heart (clinically), Dave instantly retorts with, "He's like a father to us.". His video will states that, in the event of life-threatening illness, all he wants is to spend his last days among his "friends and colleagues at WNYX".