Randolph Street has always skirted dangerously close to becoming a sort of hipster Disneyworld. It’s a safe, roomy thoroughfare surrounded by an area just gritty enough that conventioneers can feel adventurous for branching out from the Loop while hitting a one-stop boulevard that indulges any food whim in a stylish way. A sleek French bistro over here; a roadhouse-chic Mexican taquería over there. There’s a sushi bar and a trattoria and a breakfast joint, small plates of all stripes, and an army of valets to deal with the hassle that is your automobile. All that’s missing is the monorail from your hotel.

But that viewpoint oversimplifies a street whose moment in the sun has lasted a good decade longer than anyone anticipated. For starters, the restaurants have always been pretty good. From the beginning—which is 1991 for our purposes in this story—no stretch of Chicago has had a higher batting average, restaurant-wise. More than a dozen different establishments on Randolph Street have earned stars from Chicago magazine in that time, and I wouldn’t call many of them calculated. Rather, I would say restaurateurs look down the street at the competition and have learned to either bring their A-game or not to bother. There is no coasting on your address; just ask Izumi. Or Pasha. Or Veerasway or Millennium Steakhouse.

When Vivo, a loftlike Italian charmer, opened in an abandoned grocery in 1991, the Market District at night was basically skid row. Jerry Kleiner, one of Vivo’s original partners, described the area as a red-light district full of “hookers and hoboes.” But its location, near three major expressways, the Financial District, and the United Center, quickly caught on with Bulls fans during Michael Jordan’s 1990s ascension. Visionaries like Kleiner and Michael Kornick saw which way the wind was blowing and soon, the block was teeming with over-the-top glitz factories like Marché, Red Light, and Blue Point Oyster Bar. A few blocks west of the action, Jordan himself had a stake in One Sixtyblue; to the east, Paul Kahan set up shop with Blackbird and Avec. All were packed. An excitement so charged the air that all you had to do was say “Randolph Street” and there was some vague expectation of fun.

As it happens, though, the mystique faded. Too many of the restaurants went on cruise control; Kleiner’s empire withered away completely. (Vivo, still going strong, is now owned by Dan Krasny, one of Kleiner’s original partners.) I myself have written off Randolph Street countless times, perhaps most recently in 2007 when Alhambra Palace, modeled after the sumptuous complex in Andalusia, spent three years and untold millions on a 24,000-square-foot space, imported every fixture from the Mediterranean and Middle East, then forgot to serve good food. (I recall a press release that told the world the chef was “sitting idly by in his kitchen waiting to be reviewed.”)

But a funny thing happened. A new generation of consistency-obsessed restaurateurs, like Stephanie Izard (Girl & the Goat) and Brendan Sodikoff (Maude’s Liquor Bar, Au Cheval), targeted the area and recreated it in their own hip-but-populist image. “The area still has a bit of street cred,” says Chris Dexter, a partner at Nellcôte, one of three Randolph Street spots that landed on this year’s Best New Restaurants list. “It exudes an industrial, crazy-city vibe and energy, and even though it’s regenerated several times, the meat-packing-kind-of-vibe that remains speaks to our concept.” It obviously speaks to more than Dexter. I count eight promising Randolph Street restaurants on the verge of opening, including Curtis Duffy’s Grace, Graham Elliot’s G.E.B. Bistro, and Stephanie Izard’s Little Goat. Any of the eight could make next year’s roster.

Moment in the sun? If anything, Randolph Street is the sun. And the rest of us, whether we realize it or not, are but planets revolving around it.