Mourning the Death of a Legendary Diner in Toronto

“Pudding or Jell-O?” It’s a change from the choice of sparkling or still we’re usually presented when dining out, but it’s what I overhear waitress Sally Smits offer to tables who ordered the lunch special at Toronto’s iconic west end diner, Skyline Restaurant. The pudding that day is rice, the Jell-O is peach, coffee is offered before water, and the place is packed with people eager for one more meal on the 53-year-old diner’s last weekend in business.

An emblem of its Parkdale neighborhood’s previous life, Skyline remained unchanged by the area’s tense move away from staples like screaming junkies and pawn shops to tiki bars and fanciful French patisseries. With its subdued coffee stained glow and yellow bearded clientele, it repelled the areas younger condo crowd like an episode of Jag, and its menu of classics like steak and eggs, club’s, and a daily Campbell’s soup selection catered to those looking for a quiet, no-nonsense meal.

All photos by Nicole Nyholt

But Skyline’s real charm came from beyond the roster of standards it served; it was the timeless decor and antiquated flourishes that gave it character and made it feel like you’d stumbled into David Lynch’s garage sale. Things like the ornate manual register, faded postcard collections, crimson vinyl booths, classical music crackling out of an old radio, and the ominous payphone in the basement are what created the perfect ambience that made Skyline—and all great diners—such an endearing fixture of contemporary restaurant culture. Every city has their version of Skyline; those places whose charm makes you ignore that the pie behind the counter has been sitting out long enough to have begun contemplating its own existence, and where an entirely average western sandwich is elevated into something completely satisfying.

The nostalgic appeal of institutional diner’s like Skyline places them in their own category, removed from the criteria that restaurants are regularly held to, and where they please us by consistently catering to our lowest expectations. It’s where steak on a kaiser is all that it’s asked to be, where food isn’t made with a photograph in mind, and where breakfast and dinner are the same meal.

Skyline opened in 1963 and was taken over in 1970 by Louie, the Greek proprietor who you could find behind the bar mixing everything from milkshakes to $7 Harvey Wallbangers, perpetually sporting his black vest. He sold the business so he could deservedly retire, and even though he’s working his last service when I see him, he hasn’t thought much about what he’ll do next.

“I’m not there yet, [but] when I get there I’ll know” he tells me. “Something else, not too stressful.”

He sharpens his pencil, buses plates, refills coffee, and answers a phone that on any other day, I’d argue, isn’t plugged in. And during this flurry of activities, he’s still taking the time to shake hands with returning customers who stopped by to wish him well. It’s busier than I’ve ever seen it, with a mix of lone seniors, middle aged couples, and families who nod and chat with one another. Two ladies even bring in bouquets of flowers; one for Louie, one for Sally, and one for the cook, which is the entire staff for Sunday service. People standing by the register at the front aren’t waiting for change, but to say thanks.

“Good people” Louie mutters to himself thoughtfully as he waves goodbye. The notion of the diners warm hospitality has been ingrained in us through its cultural depiction in film, television, and art, but at Skyline, I truly witnessed it. As modern restaurants open and close seemingly based on what the latest trend in fried chicken is, it’s hard to imagine any establishment procuring the kind of warm-hearted, neighborly community that Skyline did.

Sara and Ian Duke, the friends I met for breakfast, first started dining there in 2002. When Ian was working at a nearby legal office, he ate there nearly every day.

“I was a lunch-dominant individual,” he explains in between forkfuls of souvlaki. “It was a comfortable environment here and interesting to look at.”

“There’s not a lot of places in the area that do a proper, traditional breakfast,” Sara chimes in. “If my breakfast show’s up and there’s green next to it, I’m pissed. You don’t put salad next to hot eggs.”

For them and many others, Skyline doubled as a place to eat and to escape the gauntlet of contemporary brunch. There were no lines, ketchup was the only garnish, and the word “fresh” had no place on the unpretentious menu. It dished out the greasily unrefined food we crave, but that articles forwarded to us by our mothers guilt us over. Even if you prefer eggs Benedicts, microgreens, and duck eggs on your menu (I sometimes do, too), we must lament the disappearance of gems like Skyline because it’s not a formula that can be replicated.

The diner can’t be built in a day, or even a decade; their menu’s items are classics because that’s how they’ve been making them for 40 years, and any contemporary iteration or “reimagining” of the diner will be judged because it’s new, and if something’s new then we expect it should be better. But the diner could never be better than what it was; it will be modern when we crave retro, the service will be intrusively mediocre when we were used to it being charmingly slow, and the food will probably have green next to it.

On February 22, Skyline officially closed, sending its dedicated regulars out into a world that’s indifferent to soup always coming with Premium Plus crackers. I’m told that the establishment’s new owners intend to re-open it.

“It will still be Skyline,” Sally told me. It will, but it won’t. She’s not sure if she will be still be working there. Those who dined at Skyline were treated to a place left unchanged during decades of changes, and a place that oozed hospitality because Louie had made it home. I do hope the new owners can maintain the magic of Skyline—we’ll just have to wait another 40 years before we can really tell.