I'm not huge on mixed drinks. The alternative choice (straight bourbon or dry martinis) usually wrecks my night, though.
I drank a lot of rum while sailing in the Caribbean this past February. My favorite concoction (other than rum and whatever random juice we had left on the boat) was a bushwacker. I hadn't heard of it before, but they had it at all the little island bars in the BVI. It's like a dessert, practically. I figure if i'm mixing, i may as well go all out. Here's my latest version:
For 4 servings
2 oz rum
2 oz spiced rum
2 oz vodka
2 oz kahlua
2 oz frangelico
2 oz bailey's
2 oz coco lopez (or coco goya)
4 oz milk
Ice, enough to fill 3/4 blender
Blend until smooth. Pour into 4 glasses. Add a dab of chocolate syrup and liberal amounts of fresh grated nutmeg to top.