* Joe's speech to an unconscious Jimmy James when Jimmy had a heart attack was surprisingly poignant. Rare because Joe was often OutOfFocus.
* For this troper, Jimmy's speech to Dave in "Station Sale" after he passes on the offer to sell counts as a CrowningMomentOfHeartwarming (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 CrowningMomentOfFunny 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 [[BunnyEarsLawyer 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, [[CrowningMomentOfHeartwarming "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".