Among the best fantasy art of contemporary 'Old School' games is that commissioned for James Raggi's Lamentations of the Flame Princess (LOTFP) products line. The above piece graces the cover of the Rules and Magic booklet for the 'Grindhouse' edition of the LOTFP roleplaying game. It is by Jason Rainville and I assume was created sometime in 2010 or 2011. More of Rainville's work can be found at deviantArt.
Raggi's game and related supplements are almost defined by the art they contain. They are generally not for children. The illustrations are often graphically violent and/or sexual, sometimes macabre and often cynical or at least, well, arch. Some would say it's nihilistic, though I don't think that gets it quite right.
I like it.
The best pieces almost always tell a story. Scratch that. The best pieces almost always tell an interesting story that makes you think. Indeed, the attraction of many of them is that it isn't completely clear what the story is. That is they are subject to multiple interpretations, and part of the fun is puzzling out which one works best.
Contrast the above scene of implicit combat with, say a typical 3e, 4e or 5e illustration. Most of those are also of combat scenes. And almost always they catch the figures in mid-jump or mid-charge or mid-something or other that is supposedly incredibly exciting. But in fact they are dramatically static, equivalent to (as has been pointed out before) an almost arbitrary screenshot from a video game.
What is going on above? The first interpretation for many is that it's a girl suddenly finding herself in the position of defending her family against some unseen attacker, perhaps someone or something supernaturally horrific. Her father is almost certainly dead-killed first (though how did the girl get between him and the attacker?). Her mother stares at the unseen (by us) attacker in fear, instinctively protecting her baby. The girl grips the adult sword steadily but awkwardly. It's obviously too heavy. How did she get it? Are the tears due to to simple terror at what now confronts her, or the realization that she herself is already 'tainted' by perhaps wounding or killing one of the attackers? Logically there is no hope. But somehow one thinks that this girl may have a chance, surprising all of us-even and especially the enemy who thought it would be easy.
An alternative view is that the bleeding man was himself one of the enemy (would her father have been sleeping in his breastplate?) that unfortunately (for him), took no account of the young girl. Who would have?
She's not a victim. She's a heroine. That's why we like this piece.
She might die. They all might die. Bad things happen-even to innocent girls. That's not cynical. Just, well, accurate. But you can go down fighting...