Well since I have more knowledge here as opposed to whiskey, I'll pop in my best Values.
Padron Londres Maduro - One of my favorite smokes period. If you like them, you can spot them online for about $3 a piece.
Perdomo Lot 23 Natural - Smooth and creamy. If you like these, get a box from The Party Source at about $2.50 a piece.
Famous Nicaragua 5000 - Available at Famous smoke shop (online) for just over $2.00 per. Like smoking a chocolate brownie.
If I can go to $5? I'll mention a few.
Lots of good Cubans in this range. If you're in America they're illegal
If you watch Joe cigar at Cigars international, you can get any Don Pepin Garcia for less than $5, Cains for under $5.
601 Blue online is less than $5 without looking hard.
Joy de Nicaraugua Antano 1970. Ditto
Oliva G, O ,and V ditto.
Tatuaje Havana VI. Ditto.
You can try one or two of each of these from a local shop (apart from Famous) to see what you like. This is off the top of my head. I could work and find 5 times more if you like. These are all strong enough to stand up to bourbon.