Roger at Roles, Rules and Rolls is the latest person I've seen posting about how D&D is not really suited for emulating swords & sorcery fiction. The theory goes: D&D is about 4 or so guys, maybe with hired help, going on an adventure to bring back treasure, while most fantasy fiction and especially swords & sorcery is about just one guy, maybe two at most, having an adventure. Of course, I think Roger's main point is that it does a good job of emulating other adventure fiction, like H. Rider Haggard, where parties of treasure seekers are the norm. And there is a point there, since A. Merritt is listed in Appendix N; "The Moon-Pool" not only has groups of about four people and an occasional hireling, but there's even a first expedition that suffers heavy losses.
One might claim that D&D doesn't emulate swords & sorcery, but rather an amalgam of literary styles, which takes a lot of its attitude from swords & sorcery, but takes other elements like expeditions from general adventure stories (or fairy tales and some Arthurian tales like "Culhwch and Olwen", where there's a group of people, each one with a specialty.) Or one could point out that swords & sorcery frequently *does* have more than two characters, but the extras are often just that: extras, sometimes without a name, usually dying pretty quickly, or taking their leave. Conan occasionally has a band of men under his command; Fafhrd and the Grey Mouser sometimes have a couple extra people in their "party", usually their current love interests like the ghoul-woman; Elric goes on at least one expedition, several wars, and teams up with other incarnations of the Eternal Champion on at least two occasions.
But I think it's much more relevant that it's not that D&D can't emulate the one- or two-character adventures of swords & sorcery, but that most groups these days choose not to do so, mainly because they are groups. Several people who have played with Gygax, including Michael Mornard (Old Geezer from RPGNet,) have said that many of the players went on solo expeditions; Mornard himself bragged about going on a solo dungeon crawl as a 1st level Magic-User. That's so rare these days that some people think it's impossible; you need a balanced party filling the four major roles.
It's not the rules that prevent people from playing swords & sorcery. It's the people choosing not to play that way.
D&D does one cunning thief or doughty warrior just fine, you just need a player who is cunning enough to survive.
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