In mulling this over, I can't really think of a bourbon that will overpower a medium to full-bodied cigar. If you had said light cigar, I might be able to break it down some, but a strong cigar speaks for itself, and when you're not sipping the bourbon, and turn back to puffing the cigar, nothing will get lost. If anything gets lost, it'll be the bourbon, until the next sip.
Go for what you know, and when it comes to bourbon, it all depends on your budget. You can see the thread with my latest Top 25 for suggestions, and there's something for every budget down to about $20-23 a bottle, depending on where you live, and what taxes are like.