If you could bring 5 people from Skyrim into a bar fight, who would that be? Chairs, bottles, mugs and other stuff from inn are allowed, but no weapons.
Now there are certain rules in it, not to make OP crew, so it would go like this;
Two people can be real brawlers, so there would go really strong lads/gails to aid you in combat.
One should be guard from any capital, just to represent your colours.
One is awesome guy. Someone with good/funny/brutal quotes, who will just sit there with mug and rant about that whole fight.
And the last one is completely incompetent fighter, one who'd do everything wrong and who'd get beat up fast, and probably moan how much he/she hates this event.
So lets start;
I would go like this:
Brawlers:
Vilkas - No brawl is won without Vilkas ofcourse.
Hrongar - He looks really tough.
Guard:
Stormcloak guard - I like blue, and I like Stormcloaks.
Awesome guy:
Orgnar - First one to approach him, he'd just reply; "I'm just a cook, lad."
Incompetent fighter:
Heimskr - He would pull aggro anyway, everyone wants to beat him up.

Anyone else?