The Canadian National Railway controlled a huge amount of land along the Lake Ontario waterfront, and to the north many firms took advantage of the easy access to rail and the harbour.

Among the industry, the area was home to the Royal Alexandra Theatre whose construction and launch were financed by four Toronto business leaders—Cawthra Mulock, Robert Alexander Smith, Stephen Haas, and Lol Solman.

[6][7] Initially unsure about what he wants to do with the newly-acquired property—and facing the drawback of being in an increasingly neglected industrial area of town, across the street from the CP Rail Yards—the businessman eventually decided to invest in an extensive renovation of the theatre.

[9][10] Offering simple food and Barnum & Bailey-like ambience amid garishly set interior featuring oversized oriental vases, red-flocked wallpaper, Tiffany lamps, bronze and marble statues, stained-glass windows, and lamps with naked women on their bases, the restaurant acted as a complementary offering to the theatre in hopes of increasing revenues for Mirvish via catering to patrons who may want to have dinner before taking in the show next door.

[6][7] Looking to reduce costs, Ed's Warehouse served a very basic pre-set menu revolving around beef (prime rib or roast), mashed potatoes, Yorkshire pudding, and gravy followed by spumoni ice cream for dessert while requiring its male patrons to wear a suit jacket and tie and insisting on it long after other dining establishments had eliminated the tradition.

[11] Paid for with a sizable bank loan the Assoons took out by putting their father's house as collateral,[14] its thumping bass could be heard miles away, flooding the deserted neighborhood with noise.

[11] Operating without a liquor licence, thus not serving any alcohol throughout its run, the afterhours club initially made a name via its Saturday night parties that went until the Sunday morning dawn featuring owners Tony and Albert Assoon spinning underground disco, funk, and freestyle tunes.

[14][11] In 1982 Roy Thomson Hall opened at King and Simcoe, becoming the new home of the Toronto Symphony Orchestra thus expanding entertainment options in the neighbourhood beyond partying at the Twilight Zone.

[14] In May 1987, popular local television station Citytv and Canada-wide cable channel MuchMusic (both owned by the same corporate entity, CHUM Limited) moved their headquarters to 299 Queen Street West (also known as the CHUM-City Building) on the northern edge of the neighbourhood.

[15] In September 1988, recent arrivals to the neighbourhood MuchMusic and Citytv launched Electric Circus, a weekly dance music show airing live on Saturdays in the late afternoon from the CHUM-City Building's ground-level studios as a simulcast on both stations.

Quickly becoming popular with the Toronto-area youth turning up to watch the proceedings in the studios visible from the street (or even hoping to get inside and dance), the show began drawing more young crowds to the area increasingly becoming associated with nightlife and partying.

Khabouth's success with Stilife made other entrepreneurs take notice; despite the Twilight Zone's 1989 closure, numerous new clubs began appearing from 1990 onward, attracted by the developing nightlife scene and still relatively cheap rent.

"[19] Canada's Walk of Fame got established in 1998, right in front of the two Mirvish-owned theaters on King St. West between Simcoe and John streets, acknowledging the achievements of successful Canadians.

In 2001, twenty-one-year-old local hospitality entrepreneur and former minor league hockey player Travis Agresti[20][21] opened Inside at 218 Richmond Street West,[22] a three-level nightclub that would become notable due to its association with the Raptors' basketball superstar Vince Carter who within two years decided to invest in the huge venue, becoming its co-owner.

[24] Though not involved in day-to-day running of the venue, Carter's high media profile nevertheless attracted a long list of visiting athletes, musicians, and entertainers to Inside throughout early-to-mid-2000s, such as Jason Kidd, Antawn Jamison, Barry Bonds, Prince, Nelly Furtado, NSYNC, Kanye West, Paris Hilton, Chris Rock, Jessica Alba, Elisha Cuthbert, etc.

Further adding to its mystique was the fact that the man behind it was Peter Gatien, legendary former New York City nightclub czar who had owned 1980s and 1990s hotspots such as The Limelight and Tunnel before being deported back to Canada.