My first drink was Coors Light and I absolutely hated it, luckily the buddy I was hanging with had Jack Daniels on hand so I got to experience the delight of mixing sweet tea and Jack together. I'd suggest staying away from light beer, until you've developed a taste for beer itself I'm not sure a watered down version of the stuff is the right way to introduce yourself to it.
Surprisingly I'd suggest trying plain old Budweiser, it's like a good starting point since it's got no real extreme taste or flavor to it. It's like the vanilla of beers in my opinion, and the nice thing about it is it's rather easy to find in most locations. I'd start with that before trying most of the light/cheap-o beers, mostly because you get less of any harsh alcohol or nasty after tastes.
If you find yourself enjoying beer, I'd say branch out to try the other regular beers before diving down the path of Malt Liquor and light beer. I've found myself partial to German beers mostly, the flavors are richer, there's no harsh chemical aftertaste with them, and outside of getting beer farts I've have no negative impacts from drinking german beer.
If you really want to venture into 40s territory I'd say find one that is still within a glass bottle, and grab yourself a fast food burger and fries to go with it. I've found Colt 45 and a Whopper go beautifully together, but just keep in mind you'll probably have to take bigger swigs of the 40 to enjoy it all while it's still cold.
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