I chose a nice blended Scotch that wasn't too peaty and a bold, spicy, Rye that would be strong enough to dance with the Scotch without being overwhelmed. A little cinnamon syrup and coffee bitters round out the drink. A twist of orange as a garnish lights up the cocktail and adds aromatics.
This is certainly not something that you can only do with these two drinks. Pairing different whisk(e)y is an art form. Some distilleries have mastered it, or at least gotten pretty darn good at it. For some examples, check out these blends:
"An Unwritten Life"
1 oz. High West Rendezvous Rye
1 oz. Great King St.
1/4 oz. Cinnamon Simple Syrup (see previous posts)
1-3 dsh. Coffee Bitters (see previous posts)