If I were starting out, I would basically try to do a “flight” of various beer styles to get a sense of what flavors work for you. Anchor Steam is always a safe bet. Sierra Nevada is a good introduction to the hoppier varieties of beer. If you want something heavier and maltier, I would suggest at least one bock beer: Ayinger Celebrator or Spaten Optimator. Also, look through your stouts: Samuel Smith’s Oatmeal Stout or Bell’s Kalamazoo Stout are good places to start (if you can get Bell’s in your region–a lot of the distribution is regional, so I’m trying to throw out mostly breweries that are widely distributed.) Hell, I even think Murphy’s and Guinness are good places to start if you want a more middle-of-the-road stout. I enjoy both of them very much.
Also, Belgians do all sorts of crazy shit with their beer and end up with a product that is often quite different than what you typically associate with beer. A lot of people who don’t typically like beer enjoy the Belgian beers. The easiest-to-find introduction to this country’s libations would be Chimay. The most common types come in either blue, red, or white/yellow label. They’re all good. If I were you, I’d buy one of each and try them over a few evenings (or one, if you’re really ambitious, although these usually come in 750ml bottles and pack an alcoholic punch.) But this is just the tip of the iceberg. There’s a lot more styles to explore in this country if you like them.
There’s just so many really good beers out there, it’s hard to exactly pinpoint a place to start. Just start drinking!