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What really goes on at the Hollywood Grill at 3 AM?

The longtime night manager tells all. Well, some.

By Georgia Hampton at Chicago Reader

At 8 PM on a Friday night, the marquee lights are winking at the Hollywood Grill on the corner of North and Ashland. It’s still dinnertime, but the restaurant feels comparatively quiet. A handful of patrons are scattered throughout the space, eating their strawberry shortcake French toast or their Drugstore Cowboy Burger deluxe, which comes with fries and a choice of soup. A man with a hand tattoo and a baby ushers two other children into a booth in the back. At the front of the restaurant, a woman loudly asks her friend at the counter if he’s noticed her new hairdo. She fluffs her coiffure flirtatiously.

But most of the booths are empty; framed collages of smirking mobsters (the casts of The Sopranos, The Godfather, Goodfellas) glower down at empty chairs. A three-tiered display of untouched cakes and pies rotates silently while Cyndi Lauper hiccups through “Girls Just Wanna Have Fun” at low volume.

The whole place seems to be holding its breath. Much later, in the wee hours of the morning, throng after throng of drunk twentysomethings will descend upon the 24-hour Wicker Park mainstay. They’ll come from Beauty Bar, from Wicker Park Fest, from other bars that closed at two. Large groups will push tables together in the main dining room, while smaller groups will be relegated to the booths flanking the windows facing Ashland. The clientele is as bizarre a hodgepodge as the items on the menu—there always seems to be a gaggle of drunk teenagers, a couple on the verge of breaking up, and some guy in Adidas slides picking up a turkey club to go at 3 AM.

“The weekend never stops,” says Perry, the shift manager. (He declined to give his last name.) Perry has been working the night shift here for 20 years but it hardly shows; bright eyes glow under his black baseball cap, and a grin peeks out from under his salt-and-pepper mustache. He looks like the type of man who dresses up for everything: even at midnight on a Sunday, he’s wearing a crisp white dress shirt and clean, black dress pants. Perry’s coy about his age. “You can say I’m a middle older person,” he offers.

Perry talks while he works, explaining his love for the night shift while bringing a tray of water to a group of teenage boys who just sat down in one of the booths; “[I like] being around different people, it’s something to look forward to while you’re working.” He interrupts his train of thought as a bearded man comes in. “You’re the pickup? Chocolate chip pancakes?” he asks, handing over a takeout bag.

While Hollywood Grill remains the go-to spot—and really one of the only spots in the area—for 24-hour diner food, Perry is quick to mention that it’s not like it once was. He describes how between 1995 and 2010, on busy nights, there used to be a line out the door and down the street. “People [would] come from all over,” he explains, “coming like [it was] an airport.”

But the neighborhood was different back then. “You remember when there used to be a gas station across the street?” he asks, gesturing to what is now a construction site for a hotel. “The hookers used to trick over there.” He describes when the buildings on Ashland were all vacant, the neighborhood was full of clubs, and the corner of Ashland and North was full of lonely businessmen with a free night and their company credit cards.

Perry describes Wicker Park back then as the place to be if you were “in search of love and good times,” he says. “A wild era, let’s put it that way. Even the waitresses were wild, like this one here.” He jokingly points to a blond woman behind the counter. She shakes her head, grinning despite herself.

Now, the vibe is more relaxed: “more calm, more peaceful,” Perry says. The clientele has changed—fewer club kids, more people in their 30s, parents with kids—though the restaurant does get its occasional wild night.

Perry certainly shows no sign of slowing down. His shift at Hollywood Grill runs from 10 PM to 7 AM, but it doesn’t seem to bother him. He says he’s been working the night shift at a variety of restaurants for 52 years. “I love the nightlife, plain and simple,” he says.

A bald man in a button-up shirt comes up to the counter to pay his tab. “You guys are really 24/7?” he asks Perry, surprised. He’s visiting from abroad and mentions how he’s struggled to find late-night restaurants in the United States. There are more than 50 24-hour restaurants in Chicago, but the man tells Perry it’s not as common to find late-night food as it is in other countries. “[Some places] close at ten, it’s crazy!”

“Not this place!” Perry declares proudly, punching in the man’s total into the register. Laughing, he adds, “not yet!”

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