Whiskey/Bourbon suggestions for newbie

Woodford Reserve is my go to recommendation for a beginner. Cheap, not too much proof, and is great by itself.

Wild Turkey 101 if you want something with slightly more proof.

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Russell’s reserve 10 or single barrel
Woodford reserve
Elijah Craig

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This man gets it.
All very undervalued at less than $40

Knob Creek, Elijah Craig, Four Roses. These are all good to sip just over ice, but you don't feel guilty if you make a drink with them. All in the $30 range. There's a bunch more, but I usually have no trouble finding these.

I like baby Saz in an old fashioned.

Knob Creek and Buffalo Trace are good to start

Gentleman Jack is also delicious with a splash of coke. Some will argue its not bourbon, but who really cares.

Elijah Craig rye is very solid for a ~$30 bottle.

Johnny Drum Private Stock or Four Roses Single Barrel are good for ~$40.

Old Forester 1910 is roughly $50 (maybe a few bucks over) and would be good for a beginner, too.

High West Double Rye will be more complex as it blends a younger and older rye. Bulleit Rye is a go to well bourbon in cocktail bars I trust. I haven't had Pendelton, but would add Rittenhouse Rye to good ryes in your price range.

As far as the difference between rye and bourbon, think about bread. Rye bread is more earthy/spicy/funky than corn bread or wheat bread. Most American whiskeys contain a combination of corn, malted barley, and either rye or wheat (a few have both). Bourbon is required to be at least 51% corn, but most also include some rye and some barley. Most cocktails include some sweetener which matches well with a spicy/funky rye. Most beginners, however, don't just go straight into drinking rye straight/neat. Most will start with a lower proof, lower rye content bourbon.

Michter's is one of my favorites in the $40 price range.

Makers 46

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Thanks for the breakdown. I think with whatever I get I will be mixing it with Coke or something else.

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In that case just buy some Jack Daniels. Don't waste money on anything decent to mix it with Coke