Good question.

It's pretty late (and I'm far too into my cups) to answer fully, but I'll give it a shot. ;)

Maker's (a mutual favorite of ours :) has a lot of cherry notes, so that would be my first "off the cuff" answer. Cranberries may work well (20 bags?!? Yeesh!), but it might take a more robust bourbon to balance them out (perhaps a more rye-centric recipe, like Knob Creek, or Wild Turkey 101 [or, my new love, WT Rare Breed Barrel Proof]). Cranberries can be pretty aggressive.