I speak as a person who ran 1E for 5 years (1984-9), 2E for 11 (1980-2000), 3E for 8 (2000-2008) and now I've been running 4E since it came out.
In terms of 'nifty things to use in the game and odd detail stuff', the 1E handbook wins hands down. 2E DMG loses.
In terms of 'things which facilitate me preparing adventures quickly and enjoyably', the 4E handbook wins hands down. 2E DMG loses.
In terms of 'cartoons which STILL make me laugh', the 1E DMG wins and everyone else is kicked down the stairs, taking 10d6 falling damage. If there's anything I truly miss from 1E, it's that 1E had a sense of humor about itself that other editions have lacked.
In terms of 'making you a better DM', the 4E handbook wins, setting everyone else on fire for 20 ongoing fire damage.
In terms of 'organization', I'm not sure yet if 3 or 4E DMG wins, but the 1E DMG DEFINITELY LOSES.
In terms of 'beauty of prose', I wouldn't give any of them an award; Gygax's prose amuses me but I really want clean, technical language in crunch stuff. I like his prose better in adventures.
In terms of 'nifty things to use in the game and odd detail stuff', the 1E handbook wins hands down. 2E DMG loses.
In terms of 'things which facilitate me preparing adventures quickly and enjoyably', the 4E handbook wins hands down. 2E DMG loses.
In terms of 'cartoons which STILL make me laugh', the 1E DMG wins and everyone else is kicked down the stairs, taking 10d6 falling damage. If there's anything I truly miss from 1E, it's that 1E had a sense of humor about itself that other editions have lacked.
In terms of 'making you a better DM', the 4E handbook wins, setting everyone else on fire for 20 ongoing fire damage.
In terms of 'organization', I'm not sure yet if 3 or 4E DMG wins, but the 1E DMG DEFINITELY LOSES.
In terms of 'beauty of prose', I wouldn't give any of them an award; Gygax's prose amuses me but I really want clean, technical language in crunch stuff. I like his prose better in adventures.