I once ate a goat eyeball. It was in a taco at the Maxwell Street Market. It was gross. But, I didn't know it would be so terrible until I tried it. And the reason I tried it is because foods that seem challenging at first often turn out to be delicious. Exhibit A: the oyster, one of my very favorite things.
When you really consider what an oyster is--a squishy little piece of meat that filters sand and whatever else happens to be in the water in which it's growing—I'll admit it's not the most appetizing idea. And yet, close your eyes, bring a raw oyster on the half shell to your nose and you'll smell the sea. Throw it back like a shot and you'll be rewarded with a cool, creamy taste of the ocean, a salty finish and sometimes even fruity, melon-like notes.
People often speak of breaking bread with others, but a couple dozen oysters and some champagne shared among friends can make even the most ordinary night celebratory. As Duncan Biddulph, executive chef of new River North seafood restaurant Kinmont, said, "Whenever there was an important event, like my First Communion or Confirmation, we'd head over to Sabatino's in Irving Park and I'd slurp down dozens of oysters to celebrate."
Even in an ocean-less city, pristinely fresh oysters are only a day away thanks to the advances of modern shipping. "This is the best place in the country to have oysters," seafood purveyor Carl Galvan of Supreme Lobster and Seafood Company (aka the "Chicago Fish Dude") said. "People stick to eating what they grew up with on the East or West coasts. In Chicago, we have no such affinity. We get everything from everywhere." (Chicago also has a storied oyster history; read more at redeyechicago.com/oysters.)
With recent seafood-focused restaurant openings such as Kinmont, Bow & Stern and Pearl Tavern—plus more on the way soon—2014 promises to be the greatest year for oysters in Chicago yet. To properly prepare you, we quizzed chefs on their best advice for oyster virgins; for the advanced oyster eater, don't miss our list of oysters to try before you die.
Don't let the names confuse you
Though oysters are named for the location they're harvested—which results in a dizzying array of names—there are only a handful of individual species. Just like wine varietals taste different depending on where the grapes were grown, oysters can have different, nuanced flavors depending on the water in which they grow. "Except for wine and grapes, I can't think of anything that is as simple and complex as an oyster," said Pearl Tavern executive chef Chris Lorenz, who keeps an oyster journal documenting the flavors of varieties he's tasted—he's slurped more than 100 so far.
Trust your server
If you're trying oysters for the first time, treat your shucker, chef or server like a sommelier and ask, "What's good?" Don't settle for one type. Try a sampling as you would a flight of wines. Grab some oysters from the East and the West coasts, and if available, the Gulf of Mexico.
Oysters that are smaller in size because of the cold waters in which they grow—such as West Coast oysters like Olympias from Washington, or oysters grown in Maine, such as Beausoleils from Prince Edward Island—are great starters. "It's no denying [that eating an oyster] is weird," Biddulph said. "How comfortable are you with big, chewy things? Imperial Eagles and Blue Points are huge. Start with something small and work your way up."
Know a clean oyster
Oysters on the half shell should be swimming in a juicy liquor (it's not alcoholic—that's the official name for an oyster's natural juice) and free of shell fragments and sand. "I have one guy, and all he does is scrub mountains of oysters all day long," Brian Greene, chef at West Town's Bow & Stern, said. "No one wants to eat a delicious, beautiful oyster and then have to spit something out." Pearl Tavern's shucker Matt Balikov wears a mini-flashlight around his neck that he uses to survey and inspect his mollusks. The oyster should be plump, and its surface smooth and uniform—not mangled, with gills and meat all askew.
Skip the sauces at first
Though oysters often are served with lemon slices, mignonette (a vinegar, shallot and wine-based dressing) and cocktail sauce, try eating them unadorned to experience their true flavor. "I would never put cocktail sauce on an oyster," Lorenz said. "Some people like ice cubes in their wine, and hey, it's like Burger King—you can have it your way. But, you never want to cover up the flavor." Once you know what you like, then add sauces. At Kinmont, Biddulph serves his oysters with a fruity, acidic hot sauce made from fresno chilis and a champagne mignonette. At Bow & Stern, Greene makes a pico de gallo-like cocktail sauce featuring smoked tomato, jalapeno and pickled red onion.
FOR ADVANCED FANS
Collectors of fine wine speak reverently of certain bottles; those who know oysters speak equally respectfully about cucumber- and melon-flavored West Coast oysters, deep-cupped Kusshi oysters from British Columbia and buttery Kumamotos from Puget Sound. Galvan said he's particularly enamored of the crisp watermelon rind-perfumed Montauk Pearls grown on the eastern tip of Long Island, N.Y.
If there is a unicorn of oysters, it's the wild, metallic-tanged Belon oyster that grows in France's Belon River. You have to travel to Europe for those, as they thus far have been tough to procure in the U.S., Galvan said. There are coveted versions of the Belon grown domestically (see map), but just as sparkling wine is only truly champagne if it is grown in the Champagne region of France, Belon oysters grown in the U.S. are not true Belons.
>>How to eat an oyster
 Pick up the oyster with the smooth edge facing you, keeping it flat as to not spill the juice
 Tip it back and slurp
 Chew a few times and swallow
Optional: Dress up your oyster with a squeeze of lemon, a dash of cocktail or hot sauce or mignonette. Some like eating them on or with a saltine cracker. (See "Oysters for beginners" to read why chefs recommend trying your first oysters without any condiments.) Though some use the tiny fork provided to ensure the meat is fully detached from the shell, that shouldn't be necessary at any restaurant with a decent shucker. –Lisa Arnett