I've recently discovered a new bourbon, Straight Edge, that I will highly recommend if you like that sort of thing.
"Straight Edge Bourbon is new and limited edition bourbon finished in used Orin Swift Cellars Mercury Head Cabernet Sauvingon Barrels for 4 to 5 months. Straight Edge is from Splinter Group Spirits, a new spirits company based in Napa Valley founded by Orin Swift Wines Founder Dave Phinney and other investors. The Orin Swift Cellars collection is known to enthusiasts as some of the most forward-thinking and appreciated wines on the market including famous labels Prisoner, Papillon, Abstract and others."
The ageing in wine barrels really give Straight Edge a supple cognac-like experience on the back of the palette. I personally find neat is best for this smooth contender. You should be able to find this around $50 USD per standard bottle.
I also would like to recommend a bourbon from my home state. Garrison Brothers, home of the "first and oldest legal whiskey distillery in Texas", is a very nice alternative to the better known higher end bourbons. It's made in Hye, TX (about an hour west of Austin). Dan Garrison and his brother started the business back in 2005 when there weren't many craft distilleries around... well, especially in Texas. He studied under some of the best master bourbon craftsmen in Kentucky to refine his skill and create what has become one of my favorite go-to bourbons. While I have not had the Cowboy Bourbon that was just named “American Micro Whisky of the Year” in Jim Murray's Whisky Bible with a score of 96, I regularly purchase and enjoy their more mainstream line at about $80 USD per standard 750ml bottle. (As an aside, the Cowboy Bourbon release has been harder to find than Big Foot in Texas, but if anyone sees it in the wild, please let me know. It launched at about $150 for a pint, but I've heard rumors the 375ml of nectar have sold in the $600+ range between private collectors).
I'd love to hear your recommendations and what your favorite labels are and why... I have had a lot... maybe not "most", but a lot. I have yet to experience my white whale, Pappy Van Winkle's 23 Year Old Family Reserve, so try not to rub it in too much if that is your daily driver.
/clayton