Ya know...Erol Otus was the most influential D&D artist for me, so I went browsing through his old OD&D and AD&D art, figuring there must have been some character depiction that inspired me... But I can't say his heroes are inspiring. Most of them seem to be having a real rough time. I mean the MONSTERS, now yes! Wow! Really, they inspire me to play monsters.
Erol must mostly have been a DM. Maybe that's how I ended up becoming a mostly DM. Erol inspired me to play monsters!
OK so I wanted to post this image by Howard Lyon from the 4e DMG to say that it inspired me to want to play a warlock in that edition, but when I went to look up the attribution for it, I discovered she’s actually meant to be a cleric (and yeah, now I can see Corellon’s holy symbol on her armor).
Thank you to @James Gasik who very kindly located the piece I was referring to - anyway yes the Priest of Mask on the left convinced 10-year-old me to make a Speciality Priest of Mask as my very first ever PC.