Well, sweetie, it really depends on the porpoise and situation. One bourbon may be fantastic on its own, for example, and be underwhelming in a Manhattan. Another bourbon may be a standout among its similarly priced peers but fall short of unqualified excellence.
What follows is a few classes and uses of bourbon and their corresponding champion that can be readily found in any reasonably stocked American liquor store. If you feel that a category was unduly omitted, shoot me a telegram.
Best Bourbon for People Who May Not Appreciate Good Bourbon:
Described by aficionados as "really not bad", this bourbon is widely available at or under $25 for a 750ml. As a true crowd pleasing bourbon, it is a perfect fit for bringing to a party where it makes up for whatever it may lack in complexity with its easy sipping flavor profile wrapped up in a price point that makes you not feel the urge to punch the one asshole that inevitably dunks four shots into a half can of Diet Pepsi and dumps it down the sink because "I don't really drink alcohol so I don't know why I poured that."
Best Bourbon for Drinking Straight from the Bottle:
Evan Williams Black Label
Punching just slightly above its weight class, this bourbon is a grizzled veteran in the category and any liquor store should be thanking you for your generosity if you pay more than $13 for a 750ml bottle. Perfect for those days when you don't have the energy to grab a glass from one cabinet over, Evan Williams Black Label has a straight forward profile of brown sugar and vanilla that delivers its message without being given room to breathe. Just remember to breathe in between gulps.
Best Gateway to Greatness Bourbon:
Four Roses Small Batch
Arguably the best value in an already competitive price range, Four Roses Small Batch offers nuance and layers, sweetness and spice in a 750ml bottle at or under $30. While it can be argued that there are better choices for mixing, it's a standout when sipped neat or on rocks.
Best Mixing Bourbon for Sweet Cocktails:
Comfortably seated among the ranks of the most iconic and ubiquitous bourbons, Maker's Mark runs around $25 for a 750ml bottle and has a wheat-heavy mashbill that comes across saccharine on its own but works beautifully in sweet drinks like an old fashioned. To elevate a cocktail with a similar flavor profile, upgrade to Maker's 46 at around the $35 price point.
Best Mixing Bourbon for Dry Cocktails:
Equally ubiquitous but not marketed quite well enough to be iconic, Knob Creek brings a healthy serving of rye and backs off a bit on the sweetness. At 100 proof and only $35 for a 750ml bottle, you get an assertive bourbon that is ideal for dryer cocktails like a Manhattan while also holding its own as a sipping bourbon.
Best Cheap Mixing Bourbon:
Evan Williams Bottled in Bond
Whiskies "bottled in bond" are bourbons that are bottled at 100 proof and are bonded and supervised by the federal government to guarantee that they have been produced under a single distiller in a single season. While the reasons for this may be a bit antiquated, it all works out to mean that you as a consumer get a consistent, quality product at a price point just two or three dollars above the black label. With a flavor profile that is similar to the black label sibling but a bit "brighter", it delivers standard bourbon flavors without threatening to overpower any cocktail, sweet or dry. Its 100 proof packs a punch, though, and makes it a price conscious daily pour.
Best Bourbon for Understanding Life in the United States Armed Forces:
Military Special Kentucky Straight Bourbon
Only available, as far as I know, in 1 liter bottles, this bourbon is bottled at 80 proof, the minimum for bourbon. With an unremarkable - even bland - taste up front, you settle in thinking it won't be so bad until you get hit with notes of cloying sweetness and a sour taste that might be considered the right flavors for bourbon by someone who had never tasted bourbon for themselves but had heard it described in great detail. The sour flavors linger until you take another gulp. Make no mistake: this is not a sipping bourbon and, if you manage to drink enough of it to get a hangover, you have more than earned your prize. Coming in at a disturbingly cheap $9.50 per liter and only available on military bases, this bourbon looks to the sacrifice and hardship endured by our armed forces and says, "That's not good enough."