This should be filed under “stuff I think of in the shower.”
A long time ago I compared d20/3rd edition Dungeons & Dragons to your standard, Wheel of Time fantasy cover art, while 4th Edition was like the front cover of a Hammerfall album cover. In the years since then, I must say my views of older and newer editions have shifted quite a bit. So I think a better comparison scale would be actual music and songs to represent each edition.
Typical disclaimer: I’m not trying to associate bands that were popular during the years these editions came out, and these are strictly my picks for songs that I feel capture the moods and memories I have tied to playing those editions.
Older Editions, up to AD&D 1e — “Broadsword” by Jethro Tull
Reasons: This song reminds me of the feelings I had glancing at my older brother’s AD&D books as a child: something powerful, epic, with imagery of valor and knighthood. Not so heavy on the magic, but filled with wonder, faith and honor.
AD&D 2ND EDITION — “Over Hills and Far Away” covered by Nightwish
Reasons: It’s that feeling of “Oh hey, I know this — but, it’s different. A bit prettier in places, a bit more refined.” Some people swear by this version, still many preferred the original.
D&D 3e/3.5/d20: “Instrumedley” by Dream Theater
Reasons: Because sometimes the beauty is found in the complexity of things. So much depth, layers, and technique. It’s daunting as all hell to play but damn if it isn’t awesome.
D&D 4e: “Through the Fire and the Flames” by DragonForce
Reason: Because upon first playing it I’m like “Holy shitballs THIS IS EPIC!” Then it got old pretty quick. I still like it, still have fond memories, but if given the choice I’d rather play Dream Theater again.
The OSR / Retroclone Games: “Riders of the Night” by Stone Axe
Reasons: “DUDE we were rocking this back in ’76!” “Dude, this came out in 2009…” “Oh, well, shit it still rocks.”
Special Mention — Lamentations of the Flame Princess: “SadoWitch” by Electric Wizard (NSFW) (See what I did there?)
Reasons: Because some people actually enjoy the aesthetic of black magic, acid, and S&M.
5th Edition D&D: “Far Cry” by RUSH
Reasons: Because it’s too new to be Old School, too old to be New School. It’s enough of a throwback to what made the older stuff good but still feels fresh. It stands on its own just fine, and there’s a lot to enjoy here. Who cares if it’s new or old…it’s
FUCKING D&D FUCKING RUSH.