In 1921, the husband-and-wife team of Harry Shopsowitz and Jenny Shopsowitz opened an 18-seat ice cream parlour at 295 Spadina Avenue at Dundas Street West in Toronto. It became Shopsowitz Delicatessen and by the mid-1940s was selling products under the Shopsy's brand name.
Harry died in October 1945 and the business was passed along to his sons, Sam Shopsowitz and Izzy Shopsowitz. They led its growth into a Toronto institution, renaming the business Shopsy's. Future Toronto Maple Leafs owner Harold Ballard is said to have been the person who encouraged Sam to open a meat-processing plant. By 1947, Sam was being billed as "the corned beef king" in advertisements.
Izzy sold his share of the business to Sam in 1969 and Lever Brothers (part of Unilever) bought the company in December 1971. Sam suffered a stroke in 1982 and died in September 1984 at age 63. After 62 years on Spadina, the restaurant moved to Yonge Street at Front Street in March 1983. Izzy died in April 1994 at age 71 after having a heart attack while in the Shopsy's restaurant. He had rejoined the business after the sale to Unilever. The Front Street location has been described as a "landmark for more than 25 years."
In 1992, Unilever sold the manufacturing division to Maple Leaf Foods. The restaurant business—Shopsy's Hospitality Incorporated—was managed by A&W for a period in the 1990s, and then bought in 1996 by a group headed by Lewis Allen. He was CEO until leaving in 2003. As of 2005, Shopsy's Hospitality was owned by Dynamic Funds.
In 2006, Irish Embassy Hospitality Group bought Shopsy's restaurant. Shopy's Deli corporate offices are located at 51 Yonge Street (and Wellington Street East), just north of Irish Embassy Pub & Grill.
In 2008, the lease expired and Shopsy's decided to move out of its famous location at Yonge and Front. In December 2009, the restaurant re-opened in the Sheraton Centre at 96 Richmond Street West in Toronto, with other locations in Markham, Ontario, York University, Toronto Island, and a Shopsy's Express Kiosk at the Rogers Centre.
- Hot dogs
- Corned beef
- Pastrami Sticks / Jerky
- Smoked meat
- Downtown Toronto, 96 Richmond West, Toronto (in the Sheraton Centre)
- Shopsy's Markham, 7240 Woodbine Avenue, Markham, ON L3R 1A4
- Shopsy's Centre Island (Located across the Ferry on the Toronto Islands)
- Shopsy’s Express at the Roger’s Centre, Toronto
- Shopsy’s CNE, Food Building, Booth #219, Toronto (operational during Canadian National Exhibition)
- Shopsy's York Lanes Mall, York University, 4700 Keele Street, Toronto
- Spadina Avenue at Dundas Street West (1921-1983) - burned down in fire
- Yonge Street north of St. Clair Avenue (1998-2005) - now a pub
- King Street West at John Street, Toronto (1994-2003) - sold to Dunn's Famous (now closed)
- Yonge Street at Front Street, Toronto (1983-2009) - lease expired by court ruling
- Mississauga Road and Derry Road, Mississauga (2004-2010) - lease expired
- Sax, D. (2011). Save the Deli. McClelland & Stewart. p. 220. ISBN 978-1-55199-583-0.
- Waldie, Paul (March 13, 2009). "Shopsy's ordered to quit Front Street". The Globe and Mail. Retrieved April 18, 2016.
- Cochrane, G. (2005). Glenn Cochrane's Toronto: Tales of the City. ECW Press. p. 78. ISBN 978-1-55022-712-3.
- Publishing, Hunter (2005). Toronto. Ulysses Travel Guide Toronto Series. Ulysses Travel Guides. p. 202. ISBN 978-2-89464-662-5.