RPGMemes

That's the dumbest argument you could make. "The little guy is intimidating because he could tell the big guy to attack" just means the big guy is the threat, not the little guy. Imagine the little guy on his own and ask if he'd be as much of a threat at the big guy on his own. Even if he tried to hurt you, how much harm could he do?

If anything, what you're describing isn't the little guy succeeding on intimidation. It's the little guy using the help action to give the big guy advantage, and it seems the big guy really needed it.

Absolutely, Charisma (Intimidation) checks make sense, but you can't threaten them with simple bodily harm. You have to threaten them socially, or with a nearby weapon, or something along those lines.