Larceny! Drink it neat, no ice no water. use a wine glass. have a glass of water on the side, not too cold. :cool:
Some good advice here...
I started on Maker's Mark and my palate has since evolved but always recommend it as a good starting point.
Hey 165, welcome aboard. Four Roses yellow label is as good a place to start as any, think of it as Baby Bear's porridge, not too sweet, not too sharp, just right.
I think starting with a couple different bourbons will help you begin learning the nuances.
Some of the easier, nicely priced drinks I've had are Buffalo Trace, Evan Williams Black Label, and Old Weller Antique (maybe cut it with water if you find it burns too much).
While I understand people saying start with Maker's Mark --- my last bottle or two tasted of pure alcohol burn, while the 50ml sized bottle I had a few weeks ago (just had an 'itch' to have a pour of it) was quite sweet and pleasant. So I'm not sure which experience to trust on that one. ;)
Knob Creek is one of my favs and sits right near the top of the price range you mentioned. Might not be the 'easiest' drink, but I find it quite rewarding... and the best thing is that it's readily available.
I'll second the Eagle Rare and 4R yellow, unless you want to splurge on one of the upper level 4R.
Rowan's Creek also comes to mind for about $35
im a newbie and i really fancy w l weller special reserve, old rip van winkle 10, lot b, 15 year, blantons, knob creek (kinda spicy), makers 46, and 4 roses. IMO (and take it with a grain of salt, but im a newbie like you) start with the 4 roses. seems to be pretty smooth and it wont break the bank. the weller is good too. cant wait to try the 107 proof weller.
Like others have said, once you get your palate acclimated to the higher alcohol content, you're good to jump off the deep end.
There's probably a range of bourbons (most have been mentioned here) that'll give you a good primer of landscape.
Welcome to SB!