I used to do a lot of Monkey Island fanart back in 2002 (some of it is still floating around online). I've been meaning to do fanart again for years now but never got around to it until now!
From my favourite to least favourite game: MI2, MI, TMI, CMI, EMI. I almost didn't want to include EMI Guybrush, but I had to be fair.
My favourite design is his MI2 look so he gets featured prominently at the top. I wanted to have him holding a syringe, but I felt that anachronism would take away from the piratey feel of the whole image so I decided against it.