"There are no rules in shots," Henry Prendergast says. He and Robert Haynes are preparing a sort of miniature cocktail inspired by the old-fashioned and modeled after a tequila shot: you lick your hand, shake some demerara sugar on it, lick the sugar, take the shot (whiskey with a little Angostura bitters in it), and then bite a slice of orange.

Shots based on classic cocktails are one part of the menu that Prendergast and Haynes are preparing for their Logan Square bar, Analogue, which is slated to open in October. Until a few weeks ago, Haynes was the beverage director at the Violet Hour (Prendergast, a Violet Hour manager, will keep working there until it gets closer to Analogue's opening date). They began their careers at the pioneering Wicker Park cocktail lounge back when it opened in 2007, starting as bar backs and working their way up the ranks. At first, Haynes says, "We had no fucking clue. I remember walking in and being like wow, I have no idea what is going on here. I liked to drink but that was kind of the extent of my knowledge."

While the Violet Hour wasn't the first cocktail bar in the city, it was the first to really capture the public's attention, and played a major role in sparking a general fascination with composed mixed drinks in Chicago. Plenty of craft cocktail bars have opened since then—Aviary, Barrelhouse Flat, Sable, the Drawing Room, Bar DeVille, Drumbar—and a good percentage of the city's cocktail bars have set up shop in Logan Square, which is currently home to the Whistler, Weegee's Lounge, Scofflaw, Longman & Eagle, and Billy Sunday (with more to come soon). In fact, Weegee's, which focuses on classic cocktails, predated the Violet Hour by about a year.

Haynes vividly remembers the first cocktail he tried at the Violet Hour. He'd been working there for several weeks before he got up the nerve to ask a bartender who'd just worked a 13-hour shift to make him a drink at 3:30 in the morning. "It was literally the best thing that I had ever had," he says. "I've never had anything close to that. It totally changed the paradigm."

The drink was a whiskey smash—one of the simplest cocktails there is. Haynes has tried to re-create it since, but can't do it. "I think you have to be soaking wet and dehydrated and hungry and then sit down for the first time in 15 hours to really get it."

Haynes insists that he and his partners aren't planning to open another iteration of the Violet Hour in a different neighborhood. Analogue "is not a cocktail bar." It'll have cocktails, certainly, but also a dance floor and DJ to make it feel clubbier. Analogue will need something to set it apart—it's opening in a neighborhood where there seems to be a new restaurant or bar announced every other week, raising the question of how many such businesses Logan Square reasonably can support before turning into the Wicker Park that Haynes and Prendergast are leaving.

Paul McGee, who was the head bartender at the Whistler from the time it opened in 2008 until he left at the beginning of last year to open the new, wildly popular tiki bar Three Dots and a Dash in River North, says that the Whistler built its reputation on time-intensive, creative cocktails—but it wasn't conceived with that aim in mind. According to McGee, the owners envisioned a simple neighborhood bar with live music and art, and when they hired him as bartender, he asked if he could put together a cocktail list. He expected to sell 30 to 35 cocktails a night, but the first Friday the bar was open they served about 230; by the time he left, they were doing 450 cocktails on a typical weekend night.

"Overnight it turned into a cocktail bar," he says. "The Violet Hour had really paved the way—a dedicated cocktail bar that was doing everything right. They were the pioneers."

When the Whistler opened, McGee recalls, there were only a few other bars nearby—the closest being Bonny's, a 4 AM bar known for its late-night crowd (now closed), and Helen's Two Way Lounge, where McGee says he used to see fights out front (a prominent gin expert from Europe who was visiting the Whistler witnessed a stabbing on the street). Now there are at least a dozen bars within a half-mile radius of the Whistler, not counting Analogue or any of the other yet-to-open places.

"Yuppies call us a dive bar because our liquor's cheap. But you know what, if you're a bozo, you're out the door." —Paul Lynn Miller, owner of Helen's Two Way Lounge

Paul Lynn Miller, 68, owner of Helen's Two Way Lounge and son of Helen Estep, who opened the bar in 1965, has seen the neighborhood change over the years—several times. "It was OK, and then it was bad, and then it was OK again," he says. "But even so, I have a man on each door." (The Two Way gets its name from the fact that it has entrances on both Milwaukee and Fullerton.) The bar has changed with the times, according to Miller. It used to be a lounge with booths, candles on the tables, a bandstand, and live polka music—the official name was the Two Way Polka Lounge. Families would come in on the weekends. "Over the years, they started picking up the candles and throwing them at each other. The clientele changed," Miller says.

The crowd the Two Way attracts is much younger now, Miller says—mostly college kids. "Yuppies call us a dive bar because our liquor's cheap. But you know what, if you're a bozo, you're out the door. Be good or be gone."

He's watched bars come and go, and remembers that in the 60s there were five other bars just on the stretch of Milwaukee between Fullerton and Sacramento (about a tenth of a mile), with a couple more around the corner. All the other bars were owned by men, Miller says, and they told his mother that she'd never make it—"and the Two Way's here and they're gone." Estep died in 2002, but Miller keeps her ashes behind the bar.

A line out the door at the Whistler is a regular occurrence on weekend nights.

Ashley Limon

At the rate things are going, Logan Square may soon boast as many bars as it did in the 60s, if not more—but the changing demographics of the neighborhood have ensured that these aren't the working-class neighborhood joints that Miller remembers. They're places that cater to increasingly affluent residents. Though not all the new restaurants and bars are upscale, nor are any of them likely to be offering the dollar-beer specials that the Two-Way has some nights.

Among the soon-to-open spots are Radler (2375 N. Milwaukee), a German beer hall that will contain a small restaurant called D.A.S.; Chicago Distilling Company (2539 N. Milwaukee), a distillery and tasting room; the Harding Tavern (2710 N. Milwaukee), from the owners of Cafe con Leche and D'Noche; Madison Public House (2200 N. Milwaukee), from the owners of Wicker Park bar Innjoy; California Point (2101 N. California, in the old Ronny's space), from Land and Sea Dept. (owners of Longman & Eagle and Parson's Chicken & Fish); an unnamed project in the works, from the owners of Scofflaw; and two new places, from the owner of pizza place the Boiler Room: Parts & Labor (Sawyer and Milwaukee), a burger joint, and Prindiville (2354 N. Milwaukee), a speakeasy-style bar.

Demographic shifts have accompanied—and are no doubt responsible for—the influx of businesses. Comparing Logan Square to that earlier poster child of gentrification, Wicker Park, is an inexact science. But in 1990, both Logan Square and West Town—the community area that includes Wicker Park, the Ukrainian Village, Pulaski Park, and Noble Square—had Hispanic populations of about 65 percent and white populations of about 27 percent (West Town's black population was just under 10 percent, compared to about 5 percent for Logan Square). Between 1990 and 2000, West Town underwent a demographic shift very similar to the one that Logan Square experienced between 2000 and 2010, with a dramatic decrease in the number of Hispanic residents (to 47 percent) and increase in the number of white residents (to 40 percent). By 2010 the balance had tipped to a mostly white population—57 percent, compared to 29 percent Latino.

Whether the same thing will happen in Logan Square is difficult to predict, but the proximity of public transportation, the affordable (but quickly rising) rents, and now the flood of bars and restaurants make it seem pretty likely. Chicago demographer Rob Paral calls it "a prime candidate for gentrification."

Paul John Higgins/Julia Thiel

Only five bars that opened in Logan Square before 2005 are still around. Nearly 20 of the neighborhood's existing bars have opened since then—most of them in the last four years—and there are another eight places (both restaurants and bars) slated to open in the next year.

The Whirlaway Lounge is another Logan Square standby, and just about anyone who's ever been there knows Maria Jaimes, who's owned it since 1980 (first with her husband, who's since died, and now with her son). A comfortable, welcoming neighborhood bar located half a mile west of the Two Way on Fullerton, its hours have changed as its customer base has shifted. Jaimes used to have a lot of retirees coming in, she says, then people in their late 30s and 40s. In the mid-90s, younger people started coming in, little by little. The bar had always opened at 7 AM and been closed by 10 PM, but when customers stopped coming in during the day, she switched to opening at 11 AM, and is now open from 4:30 PM to 2 AM.

Jaimes also remembers a time, in the 80s, when there were a lot more businesses in the area—seven bars, two liquor stores, and two social clubs within three blocks. "We're the only ones that are still here." She says she's not at all worried by the recent influx of businesses or shifting demographics, though. For one thing, more bars and restaurants in the neighborhood mean that residents can go out in the area instead of going to Lincoln Park or Bucktown.

As for the idea that Logan Square could become the next Wicker Park? "It will not bother me at all. People is people, regardless," she says. "It's all kind of people living in the neighborhood, but we've always had good people coming in. When the neighborhood was really bad, because there were a lot of gangs and a lot of drugs and a lot of prostitution, we still had the good people in the neighborhood."

Nor is she worried about being forced out. She owns the building—back in the 80s when the neighborhood was bad, it was the only area where she and her husband could afford to buy anything—and doesn't believe her customer base will disappear. "I think there's always a place for the neighborhood bar," she says.

Prendergast, who's lived in Logan Square for eight years, has seen it change plenty and says he knows it's going to keep changing. "For me, it's kind of like planting a flag in Logan Square," he says of Analogue, "saying, all right, before this neighborhood goes to the fucking dogs we're gonna build something that's gonna be cool. And that's one thing about Wicker Park. Rainbo's still here. Danny's is still here. Charleston, Gold Star—there's still those places that have been kicking it for 20 years even with all the changes."

Prendergast and Haynes, along with chef Alfredo Nogueira (Flipside Cafe, Rootstock) and investors Amanda Brimmer and Scott Crawford, are still in the process of staffing Analogue, but most of the other details have been figured out. Nogueira, who's from New Orleans, has developed a Cajun-influenced menu for the bar. Food will be served only in the early evening, after which the tables will be cleared away and the area will turn into a dance floor.

"We're trying to design in some nooks and crannies because I think that's where the fun stuff happens," Haynes says. "Like if you're in a little corner and no one can see you . . . I think that encourages loose behavior, indiscretion."

He and Prendergast want dancing, good music—what Prendergast describes as "punk-rock cocktail disco." Haynes says they're "taking cues from the punk-rock nightclubs from the late 80s. Something about that environment is really appealing . . . the kind of environment that's decadent but fun and loose."

"For me, it's kind of like planting a flag in Logan Square, saying, all right, before this neighborhood goes to the fucking dogs we're gonna build something that's gonna be cool." —Henry Prendergast, co-owner of the soon-to-open bar Analogue

Despite Haynes's assertion that they're not opening a cocktail bar, the cocktail menu is a major focus. It's divided into three sections, the first of which will be determined by the current obsessions of the bartenders who work there. Each bartender will have five to six cocktails on the menu, and Prendergast and Haynes envision it as a way to explore ideas in a new way. "Say I'm really into split-based cocktails, like rum and gin—let me explore that, get to the bottom of it," Haynes says. "You can really understand it and what it means, do it for two months, and then be like, yup, I'm done with that, let's move on."

The second section of the menu is devoted to purls, which traditionally were beers preserved with bittering agents like wormwood. "In rural England, servants had their own beer and it was often of lesser quality, so they'd spike it to cover up the taste and preserve it," Prendergast says. The idea came about when they were making bitters and soda, and started topping the bitters with beer instead. The result is a carbonated, intensely bitter drink that tastes almost nothing like beer. "It's just a really strong, bitter shot of flavor. It'll knock you on your ass," Prendergast says. Haynes describes it as a "richer, earthier bitter" than the bitterness that comes from hops. "It's less of that supercarbonated, effervescent, weed bitter, more of like the sides of the tongue."

They've been making bitters crafted specifically for this purpose, like strawberry-angelica-allspice or blackberry-woodruff-anise-orange peel, and mixing about an ounce and a half of the alcohol with three to four ounces of beer and serving it over ice. They favor clean, classic lagers that don't compete with the flavor of the bitters, and are hoping to have a local brewery make them a beer for the purls. "We thought it was something we could really tweak and make our own," Haynes says. "I don't know anyone doing purls."

The third section of the menu is the one with composed shots based on classic cocktails. "It's not just building a cocktail and pouring it in a shot glass," Haynes says. For a Dark and Stormy, for example, he imagines making blackstrap molasses in-house, infusing rum with ginger, and floating the blackstrap on top. Fizzing powder (like Alka-Seltzer) could add the carbonation.

"Our hope is that [the shots] will kind of say, OK, everyone stop taking themselves so fucking seriously, us included. Because people will probably just order shots," Prendergast says. "I think that the cocktail thing is so dressed up and overdone and mustached. I don't like the old-timey vests and 20s music. I think that is embarrassing and I think in ten years we're going to look at that the same way we look at swing dancing in the 90s and shit like that."

He's not the only one who's unimpressed with certain parts of cocktail culture. Paul Miller says of the Whistler, which is right across the street from the Two Way, "Got real highfalutin mixologists over there. Buckets of beer is what I drink. We don't make Long Island iced teas and those kind of things. We ain't got no time for that, you know."

But Miller doesn't mind the newcomers,. "There's a place for everybody," he says. "This is my little piece of the pie. I can't compete with them. Don't even want to. Don't want their clientele. Got no credit cards here. COD, thank you. That's the way I pay my bills." And he isn't worried about losing customers: college kids will always be looking for a three-dollar shot of Jameson, he says. "Give them a place to drink, and they will drink."