I always loved the Grenadier hirelings figures.
It’s just so optimistic — you’ll need to hire some dudes to carry out all the loot. There’s a “potion tester” too (above, in red, far right). I love the idea that adventurers are callous enough to hire some guy to test if the potion they pulled out of the dungeon is poison, or some other cursed item. How much did potion-testers make? Could they identify potions with a small swig like a wine tester? The list of objects useful for the manufacture of potions in the 1st edition of the Dungeon Masters Guide make potions sound pretty foul.
“Sir, I’m sorry, that ‘potion’ was just wee wee.”
You also might notice one of the hirelings is carrying away a dead body. Was that your buddy? Is he just really sleepy, or sick, or lazy? I used to think the position of the body’s hands made it look like he might actually be trying to pick the hireling’s pocket, but what kind of a thief is so desperate he plays dead to try to pick a pocket, especially that of a menial laborer who probably couldn’t cut it as a potion taster. Or maybe he’s carrying the first potion tester.
The guys with all the treasure chests make you think it must be worthwhile in those dungeons, if you literally carry out treasure by the chestful.
The photography is bad as usual but these two are a torch & lantern bearer, and of course dungeons are dark places, so they do make sense. The lantern bearer’s bent spear and facial expression make me think he’s pretty scared. The chick with the torch is one of the relatively few female figures for D&D that aren’t dressed like slave girls.
Wait a minute…
Kenzer & Co., who publish Hackmaster, put out some awesome figures (I don’t know if they still do). This guy is a pack ape. I don’t play Hackmaster but someone in the Hackmaster stall at Origins some years ago sold me a bunch of Hackmaster figures rather cheaply and gave me (& my brother who probably bought a Hackmaster DMG) a free Player’s Handbook, which mentions that although pack apes are obviously a lot stronger than humans and able to cross difficult terrain, climb, etc., they are also prone to going “ape shit.”
He came in a set with a pixie carrying a lantern, which is another nifty idea.
I don’t know if there would be much reason to bring hirelings in a 4th edition D&D game, though, since the gritty details of adventuring are not really the focus of that game, which is much more focused on combat.
I finally painted most of these guys a few years back when my gaming group had shrunk a bit and were mostly playing a home-brew version of Advanced Heroquest (a miniatures dungeon-crawl game). I never used henchmen & hirelings much in D&D, partly because we usually had plenty of players, partly habit. In the Castles & Crusades game I’m playing in now, I anticipate lots of hirelings and henchmen being hired, because we are down to three players and will need the cannon fodder.