|Image from PopMatters|
While I focus mainly on roguelikes, it bears repeating that we're still in the midst of a renaissance of challenging games. FTL Dark Souls, Spelunky, Rogue Legacy, X-COM; the list of games with harsh challenges and long-lasting consequences is a long one. There's certainly some sort of ebb and flow effect here in terms of popular opinion, but I think we could be coming to a more homeostatic point where hard games maintain their mass appeal.
The reason behind this is social: not only is it easier than ever to share the knowledge required to overcome obstacles, it's also easier to share failures. What was once a quiet, isolated defeat is now a shared story between you, your friends, and whoever was watching the stream when you decided to get cocky and look before leaping. Even if you're not playing for an audience, many single player games have created social connections through leader boards and latent multiplayer dynamics. Seeing how other players fared or watching their final moments makes death a shared experience, which helps keep the game fresh. When you're connected to other people, there's an opportunity to learn, improve, and simply laugh after shared misfortunes.
Finally, I just wanted to point out The Binding of Isaac League Racing because it's amazing. Competitive speed runs in a game with randomly generated levels? It's more likely than you think.
Yet another reason why the combination of challenging games and capture technology makes "the social death" a good death.