I'll start. I'll show off my four regular riders representing four decades. The last one isn't really classic or collectible but it's getting there.
1966 Raleigh DL-1 Tourist with rod brakes and all
1973 Schwinn Varsity nearly all original except tires, rescued from the city dump last month
1983 Raleigh Marathon also a free bike, rescued from a dumpster just before Christmas
1994 Nishiki Sport XRS my daily commuter