On Tuesday, Alabama’s expectant father posted a broken-water message on his blog, reports E!. “So I'm gonna take about a week off here, got a daughter comin' you know!" Mr. Jennings wrote. "Y'all pray for drea and hope for a good delivery of the little hellraiser. This girl sure ain't gonna take no S--T from NOBODY!" Okey-dokey!

We just hope they don’t bring their baby to any more of Kid Rock’s parties at Nikki Midtown, where The Daily Transom ran into the pregnant couple last month.

At the release party for Kid Rock’s new album, Rock N Roll Jesus, last night, Tuesday, October 10, most guests mingled in Nikki Midtown’s front bar and in the center of its massive main room. The remaining, more special partygoers, who came and went from 10 p.m. to 4 a.m., mixed themselves drinks from bottle services on three elevated, velvet-roped-off V.I.P. platforms that were lining the walls of the seemingly Miami Vice-inspired space.

Sitting on a banquette in one of Nikki’s fortified sections was Sopranos star and New York nightlife maven Drea de Matteo, 35, whose very visible pregnancy kept her sipping a steady stream water instead of Stoli. (Cindy Crawford’s hubby, the nightclub operator and former model Rande Gerber, also came out for Mr. Rock, a.k.a. Robert James Ritchie.) Ms. De Matteo and her husband, the country crooner Shooter Jennings, are expecting a baby girl, but they haven’t yet considered picking a name. “In Italian, it’s bad luck to name your kid first,” she explained, rubbing her baby-bump while Mr. Jennings, sitting to her right, flashed rocker-horns with his hands at the Transom.

Anonymity aside, the apparently happy couple is apparently very much in communication with their forthcoming daughter. Mr. Jennings, 28, who was wearing sunglasses in the dark room, often sings to the fetus through the ever-expanding walls of his wife’s stomach. Asked what Ms. De Matteo likes about her friend Kid Rock (who, over an hour into his own party had not yet arrived), she had only one thing to say:

“He’s a cocky mother fucker, and that’s cool!”

After arriving at the party some 30 minutes later, Mr. Rock, who reportedly swilled copious amounts of vodka all night, made sure to have his security team at his back at all times. According to one source involved with the event, the Twisted Brown Trucker even brought his bulky bodyguards with him into the bathroom.

On the same night, Christian Langbein, Vogue’s international fashion coordinator, celebrated his 25th birthday with a sizable squad of fellow Condé Nasties and a smattering of fetching creative types. Mr. Langbein said he chose to have his party at the Anchor because he likes its relaxed vibe and is “sick of going to things in the meatpacking district.” Though the Vogue staffer brought a horde of first-time visitors to the bar, a group of usual-suspect types could also be found. Occupying candlelit tables at the back of the long, narrow room (near the house D.J., Matt Creed) were a clutch of Anchor regulars. And they’ve come because of Lola New York.

Started by Mr. Cruickshank and two of his childhood pals, Emmett Shine and Alex Young, Lola is billed by its founders as a “lifestyle” company, but is probably best known for its clothes. (Though they make mostly hoodies and T’s, in January, Lindsay Lohan was photographed wearing a Lola hat as she made her way into L.A.’s Laurel Canyon rehab facility. The day after the pictures hit the blogosphere, the company received over 4,000 orders.) Mr. Shine, a 23-year-old trained graphic artist, oversees the company’s design branch. “It’s blossomed into … a movement. It’s organic and it’s real. It’s about putting forth ideologies that we live by to the greater masses,” he said.

“You can see the organic response from what we get—you can’t buy that, and you can’t force people to do what people do,” added Mr. Shine. “I have friends with ‘Lola’ tattooed on them. This is big …. I feel like a historian of a museum sometimes. There will be movies made about this time,” he said.

Mr. Young—the “business brains” behind the whole operation, according to Mr. Cruickshank—met the other two when he entered kindergarten at Southampton Elementary. He spoke to The Observer from Lola’s Southampton store, where he’d gone for the weekend to move merchandise. “I just do a lot of getting everything done,” said the 24-year-old Mr. Young.

It was in the kids’ hometown of Southampton that Lola found its name. In the mid-90’s, an influential batch of shopkeepers in the seaside community convinced the local police to confiscate the trio’s skateboards, and the then sixth-grade boys petitioned the mayor to set aside a recreational space for them elsewhere. The authorities gave in and paved over a pit at the top of Lola Prentice Memorial Park, where they and their growing clique would be unseen by those for whom “summer” is a verb. “We were the purveyors of the park; you had to abide by our rules, kind of like Lord of the Flies,” recalled Mr. Shine.

It’s rather fitting, then, that Lola’s new urban hangout is also off the beaten path. Mr. Cruickshank, an owner of the bar, speculates that the “Lola crew” now comprises about 100 active members, including “in-house” photographers, D.J.’s (like Vibe and Max Barberia) and people with all the right connections. “It’s like a machine—everyone is a part of this vehicle,” Mr. Cruickshank yelled over the increasing din.

One part of this vehicle is Amanda Silverman, a co-owner of the Anchor and a publicist with a list of clients that includes Charlize Theron and Queen Latifah. “I thought it would be a cool thing to do,” she said, before adding: “Like Marquis and Bungalow and all those places … we were getting too old.” The 30-year-old fame-broker was referring to herself and fellow Anchor investor Chrissie Miller, whose line of clothing, called Sophomore, is sold in Bloomingdale’s and Henri Bendel. “I really wanted to open a bar,” Ms. Miller rasped during a riotous conference call with her best friend, Ms. Silverman, and The Observer. “I didn’t want to deal with the red ropes and clipboards—there was something very dated about that, very 90’s. If anything, they’re just keeping the cool kids out,” the designer mused, before admitting that you have to “be in the know” to find her bar.

Of course, the Anchor’s initial success is due in some part to Bungalow 8 and its neighbors’ recent misfortunes. As reported by New York magazine in an article about the area’s decline, the summer of 2006 brought a slew of undesirables to Ms. Sacco’s front doorstep—namely the bridge-and-tunnel crowd, drug peddlers, prostitutes and the police who are paid to follow them. Then the widely publicized murder of 18-year-old Jennifer Moore last July tarnished the block she left long before being abducted.

Gunther Bilali, Anchor’s fourth and final financial backer, is well aware of the switch. “A lot of it has to do with the resurgence of this part of the neighborhood …. I don’t know why anyone would ever want to go to [Club Row]; it’s kind of like going to a suburban shopping mall,” said Mr. Bilali, 41.

Still, Anchor’s far-flung locale has proved no more impervious to rabble-rousers and bad press than the congested streets of Chelsea to the north. Last month, Page Six broke the news that designer Kai Kühne was tossed out of the bar after he tore the door off a bathroom stall. The bouncers might have let Mr. Kühne stick around had the drunken outburst not taken place in front of Mary-Kate Olsen and Kate Bosworth. Jason Lagarenne, Anchor’s general manager, intimated that the incident has done little to keep young Hollywood away.

Bungalow 8 continues to lift its rope for big-name celebs, but stars wishing to avoid the frenetic scene in Chelsea find the Anchor’s understated air more agreeable. People like Kirsten Dunst and Parker Posey—the indie queen’s decorator, Rafael Cardenas, is responsible for the bar’s hunting-lodge-cum-yacht-club interior—all come frequently to drink, but other A-listers are even willing to pitch in à la Lola. On a recent Saturday night, D.J. AM, who typically charges more than $25,000 for a three-hour set, spun at the Anchor for free. Ditto Mark Ronson, whose moneyed background—his mother was the socialite and writer Ann Dexter-Jones—is shared by a number of the bar’s regulars.

A massive chalkboard hung near the top shelf, listing a treasury of libations named for friends of Lola, reads like IMDb. Sopranos star Drea DeMatteo, who grew up in a Manhattan brownstone once owned by Aretha Franklin, shares her name with her favorite elixir. So, too, does Ms. DeMatteo’s boyfriend, Shooter Jennings, son of country-music legend Waylon. When dropping by the Anchor, Mr. Jennings orders up a “Shooter’s Shooter.” And the model/actress/singer Bijou Phillips, a native of Greenwich, Conn., has the title on a vodka-based shot called “Bijou’s Crack.” The board also pays tribute to Keith Richards’ daughter, model Alexandra, who enjoys a concoction aptly named “Alexandra’s Love Potion No. 9.” Like the rest, repeat customer Devon Aoki may suckle a silver spoon—she’s the daughter of Benihana founder Hiroaki—but Mr. Young was quick to explain that Ms. Aoki is first and foremost a talented model and actress.

“I’m having a hard time trying to figure out what kind of crowd it is,” said Brian Kwong, a 27-year-old E.R. doctor at St. Luke’s Hospital. After taking a few moments to look around the buzzing room, Mr. Kwong turned back and decided that the patrons were best summed up as “rich hipsters.” Another guest that evening, a 21-year-old N.Y.U. student who didn’t disclose her name, said the group embodied an “urban elite with underground sophistication.”

Sean Spalding, a well-groomed L’Oréal employee, stood in the green glow of the Anchor’s jukebox on a recent evening. It was Mr. Spalding’s first visit to the bar, and he was full of lukewarm praise for the décor. When pressed, he cited the hard-to-miss antler chandeliers as a particularly nice touch.

Spalding’s friend Ezra Alvarez, the 34-year-old executive fashion director at Details, lauded the Anchor’s ability to maintain a nice balance of glitz and grit. He did, however, turn up his nose at an unpleasant odor he claimed was wafting through the space. “There’s a slight smell of puke, but it’s not rancid—it’s like fresh puke, like on a plane,” said Mr. Alvarez. And by the bar, a striking interior decorator named Catherine Wong offered only one complaint: “I thought it would be more secret.”