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Help me towards a smooth bourbon.

Maker's Mark maybe. But if by smooth you mean Speyside-y fruity and light, that's a stretch for bourbon.
 
Speysides tend to be a bit on the lighter side, so Makers 46 might be a good choice too. It has a bit less butterscotch than Mark.
 
Woodford is gonna be probably the smoothest in the price point you're looking at. Not terribly complex but definitely smooth.
 
Sipping on Buffalo Trace as we speak and it's quite smooth. That said Makers 46 and Woodford are two quality offerings as well.

I'm traditionally a Scotch drinker myself, and find all 3 quite good. I've tried far more expensive Bourbons in my newbie journey, but these are always on rotation, and can usually be had for $25 or thereabouts.
 
A step up from Buffalo Trace, try Eagle Rare. It's a 10 yr single barrel that's smooth and a great value, in my book. It's under $35.

On a tangent, it lost its single barrel moniker due to the change to automated bottle filling, so technically you could get a bottle between two barrels that would contain juice from both. It doesn't change the quality of what's in the barrel.
 
I'm not familiar with Speyside scotch, but there are some good suggestions here. Eagle Rare has been my favorite bourbon to date. George Dickel 12 is a very good Tennessee Whisky.

Also, check out the website/app Distillr. It may help you locate some good bourbon's (and scotches, and other whiskeys) to try.
 
Elijah Craig 12. Not sure on price. Depends on local taxes, mostly. Under $32 on BevMo.com
 
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Makers 46 or Basil Hayden's.
If you can step up a few bucks, maybe Angels Envy, it's a little sweeter than some, has hints of fruit, and is very, very smooth.
If you can go up $15, you should absolutely try Blanton's -- the best bourbon <$100, IMHO.
 

Mike H

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I really enjoy Buffalo Trace. Eagle Rare (made at the same distillery) not as much.
Elijah Craig, and Woodford Reserve are also good.
 
Have you tried Rye? I LOVE Speysides and I really like Rye I've found.

Last fall I spent a week in Speyside...ended up being a very expensive trip. 48 distilleries within 60 minutes of each other, but no way to drive after all the tastings!
 
Basil Hayden, Great flavor, gentle and super smooth and complex enough to keep a more experienced drinker happy.

It was my gateway bourbon many moons ago. I always recommend it as the best beginner bourbon.
 
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