Have You Played? is an endless stream of game recommendations. One a day, every day of the year, perhaps for all time.
We had no idea what a roguelike resurgence there was going to be back when brutal yet light-hearted dungeon-running RPG Dredmor was released in 2011. Sure, a few were doing the rounds, but they were rare enough that this tongue-in-cheek take on perma-death adventuring seemed ever so special. It still is, even if what it's doing seems rather more commonplace today. It's got wit and strangeness as well as a mean streak a mile wide.
If anything, roguelike has given way to roguelite and various experimental branching off the original concept, and while Dredmor takes a ton of liberties with the original formula it is that much closer to the core - i.e. that almost every action matters. Thoughtlessness, impatience or complacency will get you killed, and in this case that means saying goodbye to a character you've potentially invested hours rather than minutes in. Going back to the very start of a Dredmor campaign is far more heartbreaking than in, say, The Binding of Isaac or Rogue Legacy.
There are roguelikes which push the suffering and tactical thinking far higher than this does, but I think it's a well-judged middleground between evil and approachable. It's got great character classes, too.