I've been thinking about the bourbon I could share with a Scotch-drinking friend that would best open up his eyes to the qualities of bourbon. It should be a pleasant transition, not jarring, and should have a mixture of familiar elements and unexpected new experiences.

For added fun, what would be a good example of Scotch that would be a "bridge" to malts that could cause a Bourbonite to stray across the pond?

I have a couple of bourbon thoughts, but will hold back for now.