In Classic;
Druid - learned the game in Wood Elf Druid town Kelethin, falling horribly to death repeatedly. Hit Butcherblock and rooted skunks before moving onto;
Warrior - wandered about Freeport area bandaging myself. Got handed Wurmslayer and went nuts in the desert. I recall afk regening on the ruins there.
In P99;
Shaman - wandering the frigid plains, taking down undead and bears. Discovered a fun farming quest for a caster mace, got so excited by the farming I recorded it. Got cocky with my mace and learned that not all guards are equal.
http://youtu.be/iVWxBiFZWvU
Now I'm wandering the Karanas, getting eaten by bears.
Paladin - I have a thing for Faydark. Beautiful High Elf in shiny plate. After a long grind I earned every one of my spells. Hunting the undead in their mountain towers. Making nice with the dwarves, in their halls of stone. Hitting newbies with Lay Hands when possible. Watching groups enter Crushbone, making me quibble about investing the time to group.
Monk - being quickly eaten by a plant in the swamp. Pummeling leeches and frogs, terrified of venturing too far. Loving every hour of the super slow resource acquisition.