I started with Evan Williams Single Barrel and Eagle Rare 10 year. Both are very smooth with Evan Williams having a slight caramel or vanilla taste. Small batch and single barrel bourbons all have a unique taste, so you should try several. Woodford Reserve is my current go to bourbon, both smooth and tasty. When I want a little more flavor I grab the Knob Creek for a sweet and rich caramel flavor, but it can overpower some cigars.
I drink bourbon neat or with 1 ice cube. I always keep a bottle of Maker's Mark around as it's good for drinking neat or mixing.