Thanks to everyone who suggested something. I've settled on a bottle of Angel's Envy.

Some great options in this thread but I can’t believe nobody has mentioned Blanton’s.

The bottle makes it feel like more of a gift, and the taste is sublime.

Basil Hayden, Woodford Reserve, Knob Creek, Angel's Envy, Old Grandad, Bulleit are all great choices.

Basil Hayden or Woodford would definitely be my first choice though.

Angel's Envy is one of my favorites. Runs about $45 here in the states and is relatively easy to find. I'm not sure if they export though.

Woodford Reserve is my go-to. It's not hard to find, it has a reliable taste being a blended bourbon, and is generally well regarded. They are a big sponsor of the Kentucky Derby, so it's got some cachet across the luxury brand spectrum. However, my grandpa worked for Brown-Forman his whole life so it has an emotional connection for me and makes me a little biased.

Weller Special Reserve (green label) is pretty easy to find these days, about $50 a bottle and considered by some to be one of the more accessible PVW-adjacent bourbons.

I'll add Booker's to this list, if your friend enjoys sour mash flavor profiles like Jim Beam/Jack Daniels. It's pricier, maybe over $100 now, and a bit harder to find.

I'm a fan of Elijah Craig, personally. I'm not a drinker, but that's my go-to when I decide I want a drink

I'm going to recommend Old Forester 1910. A lot of people prefer the 1920, which is a bit pricier, and I can see why they might, but I actually prefer the 1910. It's complex enough to think about but easy enough to just enjoy. It's got some classic sweet bourbon flavors (people usually describe the flavor as deserty: molasses, vanilla, etc.), and a wonderfully luxurious mouthfeel that's very bourbon and sticks around for a long time.

Maker's Mark is pretty popular and they have a few price tiers.

Stubb’s Hickory Bourbon BBQ Sauce

It’s not “fancy,” but Old Granddad’s Bottled In Bond is delicious. It’s just a very good, rye heavy bourbon.

I just got done living in KY for about 5 years, the one I like for a reasonable price was Basil Hayden, I think it's from the Jim beam distillery but it's not too expensive and it's nice and smooth. But there are literally thousands of different bourbon and even one distillery group might have several brand names, like the owners of Jim beam actually makes old grandad, makers mark, and knob creek as well

Elijah Craig. 94 proof. First company to age in Oak barrels. Around here 750ml goes for around 25-30 so it won't blow ur bank

Some good recommendations in this thread. You should give the following a try.

• Woodford Reserve Wheated. It's very smooth and I think it's the best value for money you can get. This is my personal favorite right now
• Michters Small Batch. Good and robust flavor
• Weller. If you can find it, but you probably won't.
• Angels Envy is very good and smooth
• Four Roses Small Batch
• Penelope Toasted is alright. I enjoyed it, but it wasn't wow value for the price. It's a good bourbon though
• 1792 is good.
• Rabbit Hole is good
• Blade and Bow is good

Crazy that no one has recommended Costco's in-house Bourbon. It's very hard to get unless you know when it's in stock, because it sells out in like a week, but at some places (DC for example) you don't even need a membership to buy liquor. It's a REALLY good Bourbon for the price. It's a little stronger and sweeter than many bourbons in my estimation, without much bite.

My buddy is a huge Bourbon snob, we did the trail for his bachelor party, and he had a few bourbon bars set up at his wedding. It was one of the five he chose to have at his wedding, and the decision was not made on cost. He's the one that introduced me to it, and it's basically all I buy now, unless I'm getting something cheap for bourbon and gingers or some other mixed drink.

Have you thought about giving him a rye whisky? It is still a very American style of whisky. It might be a neat treat to have something just a little different.

Back when I was a drinker (7 years sober now) my drink of choice was whiskey in general, bourbon in particular.

That said, the best whiskey I ever had was a bottle of Yamazaki 12 year single malt. I got it as a gift when they just entered the US market and picked up a second bottle for ~$45 at the time. Highly recommended to any whiskey drinker.

What's your budget? If your friend is into bourbon then most everything here he's probably tried. To get a unique gift bottle will cost a bit more, depending where you are.

Smokewagon Uncut and Unfiltered is Very Good pick it up if you can find it.

It's a cheap option and often overlooked, but my go to has been Jim Beam Devil's Cut for years now.