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Your top 10 FAVORITE D&D illustrators of ALL time...
1} Keith Parkinson
2} Wayne Reynolds
3} Branko Bistrovic
4} Dave Trampier
5} Damien Mammoliti
6} Erol Otus
7} Kieran Yanner
8} Jeff Easley
9} Dave Sutherland
10} Anthony Waters
11} Matt Cavotta
(My list goes to eleven cuz sometimes you need that little bit extra when you really want to Rock.)
(NOTICE: Any list with Tony DiTerlizzi can not be considered legitimate.)

John Benbo RPG Superstar 2011 Top 8 |

1). Matt Morrow
2). Larry Elmore
3). Erol Otus
4). Keith Parkinson
5). Jeff Easley
6). Tony DiTerlizzi
I'm not good with names...so I stop at six, but with the exception of Matt Morrow, basically the pre-3e D&D artists. I do really like some of the character/monster illustrations in the Paizo books, but in the APs, I'm not sure who's is who.

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@ Derek,
Yeah, that's ccol -- lots of gamers Love DiTerlizzi's work. I never liked most of his drawings and wouldn't include him on my list but I knew if I didn't put him somewhere in the OP lots of folks would ask me how I forgot him so I added the disclaimer.
If I were the OP I'd probably have put a similar disclaimer regarding WAR. I know Paizo fans love the guy, and I'm sure he's an incredibly cool dude, but if I could tear the covers off of my rulebooks and retain their value I would...

drunken_nomad |

8. Jeff Dee
Bill Willingham
BROM
Phil Foglio
Elmore for this cover of Dragon 140
Daniel Horne for Dragon 119's cover and 126's cover

Aaron Bitman |

W E Ray wrote:Having started playing DnD in 1979 he is just the Iconic artist to me. I love some of the newer artists as well but Erol Otus will always be my favorite.@ Big Killa,
A gaming buddy of mine got Erol Otus to do the artwork on her Homebrew Campaign Setting about 3 years ago.
Gee, I got started with the old Basic Set with the Erol Otus art... but the only D&D artist I've ever particularly admired, or regarded as iconic, was Larry Elmore.
(Then again, I don't pay much attention to art in general.)

SuperSlayer |

Easley really made an impact with his art in my imagination. All the other artists listed here are great too and I really enjoyed most of the artist from AD&D 1st&2nd editions. Most all the artwork for all the campaigns was great from Dragonlace, Al Quadim, Spelljammer, Dark Sun, Ravenloft, Forgotton Realms, Greyhawk, and all the source books just had magical mezmorizing fantasy art. If any of these newer RPG's can make artwork as good as AD&D did it would catch my quick.