After years of neglect, during which much of this area's architecture was destroyed, the South End made a big comeback in the 90s and still goes strong, thanks in part to the gay community. For all, take the Orange Line to Back Bay.
They have Chimay on tap (for those 21+). And if you don't know the significance of sharing four Chimays with Italian nachos (served with feta cheese instead of cheddar), then keep on walking to Shey's. That's the lineup: Chimay on tap, Italian nachos. A close third is the semi-functioning Wurlitzer at the back - semi because it's still lit and the bubbles still climb, but the records don't spin. Oh, and the rest of the menu can't be beat and is served late.
433 Columbus Ave., Boston. 5 p.m.-1 a.m., daily.
Bob the Chef's Jazz Café
It's been around for so many decades that many of the people who work there can't even tell you how long Bob the Chef's has been in business. The one time dive-like diner that only served breakfast and lunch has undergone a number of transformations over the years and is now a sort of yuppified jazz supper club, complete with recently painted orange walls and an eclectic crowd thinking they're enjoying authentic soul food. Unfortunately, the barbecued ribs, though gooey, aren't barbecued and the catfish isn't exactly jumping off the plate. But the place is always packed and the music always pops.
604 Columbus Ave., Boston.Mon-Wed 5 p.m.-10 p.m.; Thu-Fri 5 p.m.-midnight; Sat 11:30 a.m.-Midnight; Sun jazz brunch 9:30 a.m.-2:30 p.m.; Sun dinner 2:30 p.m.-10 p.m.
(617) 536-6204 www.bobthechefs.com
Charlie's Sandwich Shoppe
Back in the days when hotels were segregated, Charlie's Sandwich Shoppe was one of the few places in town where black jazz musicians could find late-night food after a gig. Though the hours have changed, little else has in the greasy spoon that has been serving breakfast and lunch in the South End for decades. Like an old-fashioned diner, complete with swivel stools at the counter, Charlie's serves up hearty American cuisine. Shovel down the infamous turkey hash.
429 Columbus Ave., Boston. MBTA: Orange Line.
At first glance it looks like a dive bar with an unusually cheesy décor. But the Elvis shrine, the pink Cadillac, the Santa Claus outside the restrooms and, of course, the album covers lining the walls are part of what makes Delux Café one of the true gems of the restaurant-heavy South End. It's the real deal with a truly eclectic clientele, plentiful drinks and a creative, well-prepared menu that changes every six weeks. Enjoy a grilled cheese at the bar where the Cartoon Network plays nightly. Number one in the hood, G.
100 Chandler St., Boston. Mon-Sat 5 p.m.-1 a.m.; Sun closed.
It's no coincidence that the Shawmut Avenue section of the South End underwent a gentrification around the time that David DuBois and Maureen McLaughlin opened the doors of the Franklin Café. The eclectic American eatery became an instant hit because of its impeccable service and seasonally-changing menu, not to mention hip, vibrant bar scene. Don't be scared by the prices - a fish taco is under 8 bucks.
278 Shawmut Ave., Boston. MBTA: Orange Line to Back Bay. 5 p.m.-1:30 a.m., 7 days.
(617) 350-0010 www.franklincafe.com
Mike's City Diner
Near the end of his presidency, Bill Clinton stopped in for breakfast at Mike's City Diner, devouring the eggs and grits while raving about the ham cut from the bone. The high-profile visitor didn't do much to put the place on the map, but he didn't need to. For years, Bostonians have flocked to Mike's for an eclectic menu, generous portions (especially of mashed potatoes) and great prices. When South End natives, South End boys, cops, truckers and hospital workers all sit down for breakfast at the same time, even the people-watching at Mike's becomes a treat.
1714 Washington St., Boston. 6 a.m.-3 p.m., daily.
Nashoba Brook Bakery
Nearly five years ago, Concord-based Nashoba Brook Bakery, known for their 100 percent organic breads, opened a café on the Back Bay/South End line and locals soon discovered that the soups and sandwiches are just as hearty and appetizing. Still, you go for the soul-satiating, anti-Atkins creations, including the finest sourdough, french, 7 Grain, rye, olive, pepper jack, rosemary garlic and raisin breads in the area.
288 Columbus Ave., Boston. Mon-Fri 7 a.m.-6 p.m.; Sat 8 a.m.-5 p.m.; Sun 9 a.m.-5 p.m.
MBTA: Orange Line to Back Bay. (617) 236-0777 www.slowrise.com
More South End restaurants