In my experience with trying to get people into bourbon (or liquor in general), the bottle you choose has to have these 2 qualities, if not others as well:
1) It should have the quality people always describe as being "smooth", which I guess means they don't like the anything too spicy or the burn that comes from drinking spirits. So I think you want something not too high in rye and not too high in proof.
2) As stupid as it is, if you're not doing it blind, the bottle has to have some sex appeal. A fancy bottle added to buzz words people know (small batch, single barrel, etc.) and you will be on your way to winning them over.
My go to is usually Eagle Rare SB. Nothing offensive, 90 proof, mashbill is high in corn, good looking bottle, and "single barrel" written on the label.
VW Lot B works well for this purpose, for the same reasons. However it costs more ($20 more in OR), and the ERSB is probably the better choice.
"Remember that your sense of humor is inversely proportional to your level of intolerance."
- Serge Storms