I've been a Maker's Mark guy for 20 years. I learned whiskey when I was in high school because my dad always had Jim Beam in the cabinet that he occasionally drank.
When I turned 21, I would go hang out with some other IT guys that worked for the federal govt at a local bar. They started ordering Crown Royal and Ginger Ale....then we switched up to Maker's Mark and Coke. That helped me ease into it because the Maker's made Crown taste like water. Now I drink Makers on the rocks because I'm a cold drink guy. I wouldn't dilute scotch...but I drink it fast, so it doesn't get watered down. Even neat, Maker's tastes like water to me. I have a few bottles of Lagauvulin that have far more flavor and scream PEAT. I bought a few bottles of Blanton's and have a full one in my stash. A lot of people claim it's the best, but to me, it's just the sweetest flavor and that's why people claim it's "smooth". I drink it neat because it's $65 here for a 375ml bottle...when I can find it. I'd rather stick with Lagauvulin @ $140 a 750ml bottle..it's only $5 more.
I like Bulliet Bourbon...started drinking that maybe last year when all the Disney bars served it in their signature cocktails....it's pretty good and cheap, but haven't had it in a year because it mixes good with everything. I have some Henry McKenna, Baker's, and Booker's in the cabinet that I also drink neat or on the rocks...just depends on my mood.
I never cared for Woodford because it's took oakey and dry. I don't care of Jack Daniels. The only time I've EVER ordered it in a bar was when I was in Italy....just to drink it on the other side of the world.