If you’re getting into Bourbon, do some reading about who is actually making the ones you like, then try some other brands owned by that distiller. There are only four or five companies that make or own almost all of the brands you commonly find. Personally, Heaven Hill has become one of my favorite Bourbon distillers, so I’ll try or buy about anything they produce. Among their commonly-found brands are Larceny, Henry McKenna, Elijah Craig, and Evan Williams (winner of my “Wow, this is good and amazingly cheap” award, especially the White Label Bottled in Bond). Heaven Hill makes a green label Evan Williams that is younger & even cheaper (supposed to be $8 to $9), but has limited distribution. Haven’t tried that, but if anyone can make such a thing that isn’t complete rotgut, Heaven Hill can.
The other interesting thing to look for is how many small brands don’t actually make their own product. Look for small print on the bottle or label, and if it says “Distilled in Lawrenceburg, IN” then it was made at the huge MGP of Indiana distillery, then just bottled by someone else under their brand. MGP offers a very wide variety of mash blends, aging times, and liquor blends, so it doesn’t all taste the same. They won’t reveal their customer list (despite the Lawrenceburg, IN label being a dead giveaway), but the big guys buy a lot from MGP, too. Its biggest customer is Diageo, a trans-Atlantic behemoth formed by merging Guinness and Grand Metropolitan (who already owned Heublein’s former liquor division, which included Smirnoff & the US rights to a lot of big brands like Jose Cuervo and Guinness products). So if you have an assortment of US bourbons and whiskeys, there’s a good chance a lot of it actually came from MGP.
The best example of MGP’s dominant place in distilled liquor is rye whiskey. Most distillers don’t make their own rye, they buy it from MGP by the barrel or traincar & bottle it. Here’s a list from the Wikipedia page about MGP giving the known brands that buy MGP’s 95% rye mash bill bourbon: Angel’s Envy, Bulleit Rye, Filibuster, George Dickel Rye, High West, James E. Pepper, Redemption, Smooth Ambler, and Templeton Rye.
Some of those brands blend different whiskeys in (often also purchased from MGP) and add more or less water to set themselves apart, but try a blind taste test with a few of those. Some will taste exactly the same because they literally are the same thing. Add a little more water to a higher proof version & then compare it to a lower proof version. They should taste very, very similar.
I like Bulleit’s regular bourbon, but it is an interesting pile of marketing bullshit, too. Seagram bought that brand from Tom Bulleit in 1997, and started having it made at their Four Roses Distillery (which has since passed through several hands until ending up owned by Kirin Brewing). Diageo bought the brand from Seagram, and marketed Bulleit to huge commercial success. But there was no Bulliet distillery until Diageo opened one in 2017. Bulleit doesn’t have an age statement, other than it is aged “at least six years.” So all of the regular Bulleit we’re drinking until at least 2023 will still be stuff distilled at the Four Roses plant by Kirin. Despite the shiny new distillery, they still aren’t making their own rye either, they are staying with the MGP stuff. Not exactly the “Frontier Whiskey” story the marketing campaign pushes.