6. Lane Pryce
Showcase Episode: "The Good News"
The most poignant character — the British business brain who gets brought in to fire people, but ends up desperately yearning to be one of the Americans. ("I've been here 10 months and nobody's asked me where I went to school.") He bonds with Don over Japanese monster movies and hookers; he falls in love with a Playboy bunny; he repeatedly shatters the hearts of us poor deluded Joan/Lane 'shippers. He left a little chewing gum on the pubis of our hearts. Huzzah!