Mistwell said:
If the goal is to intimidate a guard into letting you through an otherwise open gate, the Ogre is going to accomplish that job better than the Halfling, no matter how charismatic the halfling is, or how uncharismatic the Ogre.
If the gate belongs to a great enough town, there will be quite a lot guards around, and they'll probably in line already. So the moment the ogre lifts his club, he'll be pierced by a volley of arrows, with halberds following.
If it's a small town, the ogre can just grab that guard by the collar, lift him up and say him: "you attack me, you die". This will be no intimidation. This will be a blank statement.
The halfling you mentioned will walk up to the guard, beckon him to lower his ear to his mouth, and tell him that he'll enter that door, or the guard will have an accident sometime the next two months..... The other guards won't hear that, but the guards will just about believe that (especially because that halfling is really persuasive)
Intimidate is not just threatening someone. It's an art, a skill. Someone skilled in it will be able to convey to the victim that making things complicated will result in very great inconvinience, but cooperation will be a good way out. It's not just shouting "you give me sword or me smash you".
