The company was founded in May 1987 and at one point claimed to be the third-largest player in the Canadian video rental industry. The video game subsidiary Microplay was founded in the late 1990s in order to facilitate the rentals of video games. In 2004, due to financial issues that had been prevalent for many years, the assets of the chain were purchased by Quebecor Media. This resulted in the re-branding of the stores with the current logo.
As of late 2011, the Jumbo Video banner consists of 17 stores in Ontario and Atlantic Canada, some co-located with Microplay. A plurality of locations are in Ontario (6). On Prince Edward Island there remains one location in Charlottetown following the Summerside store closure in 2014.  The chain was previously publicly traded as a company called Jumbo Entertainment Inc. After selling its assets to Quebecor, the remaining shell company agreed to a reverse takeover by clothing retailer West 49.
Jumbo Video currently offers a "Movies Nonstop Program". It is a monthly subscription at $9.99/month which allows the rental of up to three non-new release movies at once. Those without a plan, or who want to rent more than three discs, can pay a fee to rent a movie for a limited amount of time.