I like playing rangers.  When Third Edition came out I decided to try out clerics.  It was a rough ride, but I am now familiar with their lower-level post-AD&D spells.  I was always keen on providing healing, and am pretty good at buffing & debuffing.  Now that I have adapted to being an artillery target, I sometimes play an AD&D magic-user.  Though I am no match for my former peers, there are few retro-gamers around with the tactical mastery needed to handle old-school weirdness.  I like thieves or rogues, though I have a grudge against segmented movement ever since I was unable to prevent a cleric from incapacitating me in a 1-on-1 side battle.  Fifth Edition handles it a lot better, and at least Pathfinder gives you a way to get around the "5-foot step."  I try to stick to the defensive ranged paradigm, but do play some hybrid builds like bards & scouts, and warlocks are great even in Fourth Edition!