Looking for wisdom to go with my age.

So, in about a month and a half's time i will turn the ripe old age of 21. for those of us in the united states, this mean i will then legally be able to consume alcohol. unlike most my age however i will not be in a bar slugging down shots untill the verge of death. i prefer quieter settings. anyways, i took a trip to mexico about 9 months ago and was able to sample some beverages down there. i have come to the conclusion that i prefer Whiskey (whisky bourbon or scotch as well i suppose from what little i know) to other alcoholic beverages. My question to you guys is what would be a good first bottle of whiskey to invest in and what would be a good stogie to enjoy with it?

the whiskey's (or variations) i have tried.
Crown royal, (not a fan)
Canadian club (liked it)
Jim beam (liked it)
SOCO (i mean its sugary so i liked it)

Cigars i currently have....
Oliva Master 3 robusto
cohiba red dot robusto
flor de oliva robusto
la aroma de cuba cetro
camacho slr maduro toro
oliva serie g torp
padron 2000 (i think) robusto

you guys haven't steered me wrong yet, thanks in advance for the advice.

Can't go wrong with Gentleman Jack

I remember turning 21 and "investing" in a bottle of whiskey. I think it was Jim Beam. I mixed it with Dr. Pepper, and it almost lasted through the weekend.

On the other hand, if you really want a good bottle of whiskey to commemorate this occasion you won't remember a year from now anyway, go with either Maker's Mark or Woodford Reserve. Do yourself a favor, and stay away from the blended scotch. There's a thread somewhere in here about single malt scotch, check it out. I personally had to evolve from whiskey to scotch, and that took at least 5 years. I still keep a bottle of Maker's Mark on hand, and usually keep a bottle of Bacardi 151 (for cooking) on hand, but scotch is the prevailing brown liquor in our cabinet these days.

Midleton Very Rare Irish Whiskey. Fairly pricey but as long as you aren't going to be using a funnel it will last a while and be well worth the $.