I have been a bourbon taster for about a year now. I have a collection of about 15 or so bottles of darn good bourbon. But these are the ones I always have on hand and drink mostly:
Wl Weller SR 7y/o. This is an easy to drink bourbon and goes well with mixers, tho I like it on the rocks. Hugely cheap at $22/1.75ml.
Fighting Cock. Heaven Hill obvious copy of WT101. Great mouth feel with nice rye kick. Great value at 15.99/750ml.
Wild Turkey 101. I was late to try this one, but better late than never. WT101 is probably the best bourbon you can get for less than $20. Its at least the best of the high proof brawler class of bourbon. A well made classic.
Knob Creek. My favorite at this point in time. At $25, it's not cheap, but I can afford it and a friend likes it so its always on hand.