If you liked Candyland, you'll LOVE Cartagena (http://www.boardgamegeek.com/game/826). It's Candyland for grownups, full of delicious, take-that fun.
And it's got pirates.

Risk, a skill game? Hahahahahaha! Struggle of Empires leaves Risk players weeping quietly, and has very little of its luck. Not to mention it won't let you hole up in Oz.

Thanks for your awesome list. It takes me back. Though I echo what others have said: it's time to update the collection. Wits and Wagers is a GREAT party game. For Sale and Razzia! are fun, too. Settlers of Catan beats the pants off Monopoly (and I'm a former competitive Monopoly player--Illinois is the most landed-on, but St. James is second-most). Bohnanza is the most fun you can have playing cards with your clothes on (but no one says you have to).

I'd love to see a post about your game group tackling some of the post-1960s games!