OD&D: fighting man. I went through so many of these... until a run of good luck, high hp, and finding a magic sword +2 (big deal back then) lead him to one great victory after another. My fighter living meant the other party members lived as well, so the whole group (with the exception of a few thieves) had long careers.
AD&D: Elf multiclass (you had level limits but you could really shine),
Dual class human Fighter/Thief. You couldn't see in the dark which stunk, but the extra hp made you a great goto guy in the dungeon. Became a spy for the kingdom.
Half-orc fighter/assassin I didn't expect to live but I did. Developed a network of connections to guilds and became something of a underworld kingpin.
2E: Didn't play much 2e but did have some success as a Druid
3e: First time I could play really weird stuff so I took advantage of that. Played Bugbears and Acolytes of the skin and other unique combos, My strange characters didn't see me shine though, and the RP seemed to take a back seat. Wizards turning into hydras and pyrohydras stole the show.
4E: Warlord: great fun if you are the only one, not as fun if everyone wants to be one. Randomly add quotes from war movies for easy laughs: " I've seen it happen, Ia Drang in '66, They cut us to ******* pieces!"