Lower Tier - Evan Williams Bottled in Bond is the best deal in bourbon. You can get a handle (1.75) for $25-28. You can sip it or mix it. Wild Turkey 101 is also a good deal. Handle is around $35. Also like Four Roses base level in that price range. Also, pretty much any bonded bourbon (BIB) is good, even the cheap stuff. Early Times BIB is outstanding. I also love Old Grand Dad BIB and though not bonded OGD 114. It's the same base juice they make Basil Hayden's from. Hard to find but very good is Very Old Barton. I've had the 86 and 90 proofs. Prefer the higher proof but both are good. If you just want a tailgate bourbon for super cheap get McKenna (not the 10 year BIB) or Benchmark. That stuff is basically free and mixes a fine bourbon and coke. Also consider Mellow Corn BIB corn whiskey. Google it. Good stuff.
Mid-Tier - Buffalo Trace and Eagle Rare when you can find them. Both are allocated now so harder to find but I do on occasion. For stuff you can find, Russell's Reserve, Cooper's Craft 100 proof, Smooth Rambler Old Scout. McKenna 10 went to allocation after it won international whiskey of the year in March 2019 and it was a steal at $28 before that. If you can get it around $40 do it. I'm seeing mostly $59 now. Dude in Florence wanted $99. Nope. Knob Creek is very good and Old Forester 86. Makers Mark is fine as an introduction bourbon but it isn't very complex. It's wheated so it's softer on the palate. I prefer my bourbon challenge me to a fight but have good technical boxing skills. Their 46 and cask strength are better.
Upper - the Angel's Envy line is nice, as is Belle Meade Cask Strength Reserve. I don't buy much high end as there are too many reasonably priced bourbons. I've had Pappy 23. It was delicious. So is a lot of stuff I can actually buy and buy at reasonable prices. People recommending Pappy and Weller must live on the yellow brick road because I haven't seen that stuff outside of a glass case in a long time. The hipsters jacked the price up as with McKenna 10. Find something you like and can buy on the reg and stick with it. Don't go chasing waterfalls. The high end Old Foresters are all good. I particularly like the BIB and the Statesman.
Irish Whiskey - Jameson is good but they now have one aged in stout barrels that is more complex but still easy to drink neat.