I’m pretty sure this picture comes from Darlene’s apartment in Chicago, where she attends art school. Some of the posters that she had in her room, like the Golden Age one, made the move with her, but then there were some new ones like the Batman Grendel poster above Roseanne and to her left. Here’s what the full poster looks like.
I haven’t read either of the two issues from this 1993 crossover: Devil’s Riddle and Devil’s Masque. In fact, I’ve never read any Grendel comics, though I’ve been curious about it thanks to the fact that I’m a gigantic fan of Matt Wagner’s other creator owned character Mage. Wagner wrote and drew these two issues. This was followed up by another crossover in 1996 and everything was collected in the 2008 Batman/Grendel TPB.