I am having another pineapple and whiskey drink and thinking that combination has to be my favorite. And everyone to whom I've recommended it seems to love it. I put whiskey in my pineapple upside down cakes now, even. There is just such an affinity between the flavors.
Look up the Golden Crown by Katherine Bouchel for the syrup recipe and another whiskey/pineapple drink.
I realized I didn't answer which whiskey - honestly I think the best with canned pineapple juice is Irish whiskey, when we are out, like at a festival , pineapple juice and Jameson is one of the most reliable things you can order.
Bourbon with fresh pineapple juice.
Scotch in pineapple tepache is amazing, and I bet the roasted pineapple syrup would also be a good match.
So, all sorts of whiskey I think probably have some pineapple match.
Whisky or bourbon pair SO WELL with fruits of many sorts. I'm on a big bourbon and grapefruit kick making Brown Derby's, bourbon palomas, that sorta thing.