- 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.
- Jimmy's speech to Dave in "Station Sale" after he passes on the offer to sell (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".
- Bill has kind of a screwed-up relationship with Matthew, repeatedly walking all over him as Matthew worships the ground he walks on. This can be expected, given the man views his nightmare of a childhood with nothing but fondness. What really demonstrates that Bill actually has some respect for Matthew is when Matthew is fired. Bill goes out to break the bad news, since Matthew looks up to him, and he does it with a great deal of tact and support and none of his usual self-inflated blustering. He even breaks down in tears once Matthew's finally left the building. He doesn't hate Matthew, he just doesn't know anything else most of the time.