If you want to make a good mixed drink with bourbon/whiskey, there's only one option: Manhattan/Rob Roy
Put about 2 oz whiskey, 1/4-1/2 oz sweet vermouth, and if you're feeling sissified, a little cherry juice into a shaker with some ice. Stir; don't shake. Pour into glasses (martini glasses ideally) with a cherry, and enjoy.
Anyway, I like it. Don't listen to people who'll try to tell you that Jack is the be-all end-all of whiskeys. It's not the best, but it's damn good
Just a suggestion.