Food, drag and 20 years of community: the story of O’Grady’s on Church 

On a warm Friday night on Church Street, the lineup outside O’Grady’s on Church stretches past the neighbouring storefronts. Inside, a drag show is about to begin. The patio, which seats more than 200 people, is full. The kitchen has been running since 10 a.m. and will not stop until 2 a.m.

Jimmy Georgoulis has seen this scene play out thousands of times since he opened O’Grady’s in 2004. He started in the restaurant industry at 13, bussing tables and running food. Forty years later, he runs one of the most recognizable venues in Toronto’s Church and Wellesley Village. He does not seem tired of any of it.

A fresh start in the village

The space at 518 Church St. was not always O’Grady’s. It was a place called Wild Oscar’s. When the address became available in 2004, Jimmy saw what it could be.

“We wanted to give the village something great, something fresh, something new. Something exciting to bring the community together.”

He had already run an O’Grady’s on College Street during the Irish pub boom of the late 1990s and early 2000s. This time, he wanted something different. The team renovated the space, relaunched it under the O’Grady’s name and got to work building a local institution.

The kitchen does not cut corners

Order the fish and chips at O’Grady’s and you get beer-battered fish with homemade coleslaw and tartar sauce, plus wedge fries. The hot sauce on the table was made in-house. So was the wing sauce. So was the salad dressing.

This is not an accident. Jimmy’s executive chef builds most of the menu from scratch, and Jimmy is clear about why: a Greek upbringing, a lot of home cooking and a genuine aversion to food that comes out of a box.

“Being fresh, being unique and different, offering things that other people don’t offer at other local pubs is really important to me.”

He surveys customers. He holds menu meetings with his team. He adds things people ask for and keeps the items they love. The three top sellers, for the record, are the homemade mac and cheese squares, the deep-fried pickles and the goat cheese balls. Ask Jimmy for the single best thing on the menu, though, and without much hesitation he lands on the chicken Cobb salad.

“It’s probably our number one selling item on our whole entire menu. People love our chicken Cobb salad.”

Dinner, drag and a packed calendar

A meal at O’Grady’s is, more often than not, also a show. The venue runs drag brunches every Saturday and Sunday, both of which sell out. Friday and Saturday evenings bring the dinner and drag show. Through the week: karaoke, trivia, dirty bingo, open mic nights.

The venue also handles corporate catering and private events, drawing clients from the financial district. During the Pride weekend, the restaurant is packed. “It’s really busy. It’s really long hours. It’s really stressful. But at the end of the day, we’re all happy bringing people together to celebrate Pride.”

The safe space was the whole point

Pride Month is O’Grady’s busiest time of year, which makes sense given where it sits. But the connection to the village runs deeper than geography. Jimmy built the place with inclusion as the foundation, not an afterthought.

“My original vision was to create a space, a safe space, that would welcome everybody. We wanted to serve great food, homemade meals, excellent handcrafted cocktails. We wanted to provide a great service, a safe space, a wonderful space for people to come and enjoy with friends.”

Twenty years in, that vision holds. The drag programming sells out every week. The patio fills. The kitchen keeps going.

Keeping up with the volume

Running a 200-person patio, a full entertainment calendar and a catering operation takes more than good food and a great vibe. It takes infrastructure that works when things get busy.

Before COVID, O’Grady’s switched to wireless payment terminals through Moneris. The difference, Jimmy says, was immediate: faster transactions, better service and the ability to move across a packed patio without dragging guests to a fixed terminal. The venue also uses Moneris gift card services as part of its regular operations.

For a venue built around speed, hospitality and packed service windows, that flexibility matters.

Forty years of advice in three sentences

If you are thinking about opening a business, Jimmy has something to say to you. It is not particularly gentle, but it is honest.

“It’s not a business, it’s not a full-time job, it’s not two full-time jobs. It’s a lifestyle. You gotta breathe it, you gotta live it, you gotta be it. You gotta be your own brand.”

He also says this: be there. Not occasionally. Consistently. A business without its owner present, he believes, is a business that will not last.

O'Grady's on Church is open daily from 10 a.m. to 2 a.m. at 518 Church St. in Toronto. Whether you're stopping in for a bite, catching a drag show or booking a private event, there's always something on. Reserve your spot at ogradysonchurch.com.