Founded in 1987 by Steve Solomos and Sean Scoffield on Harbord Street near the University of Toronto in Toronto, Ontario, Canada, The Beguiling quickly built a reputation for the diversity of its stock, focused on art-oriented, avant-garde, underground and alternative comics—"anything that is even peripherally comic book-oriented", according to current owner Peter Birkemoe.

It also built a reputation for stocking the works of cartoonists such as Chester Brown and Julie Doucet, whose comics most stores would not handle due to the controversial nature of their contents.

[1] Well-known Toronto-based cartoonists such as the trio of Brown, Seth and Joe Matt became associated with the store,[2] and sometimes depicted it in their comics.

[1] In 1998, Solomos and Scoffield decided to devote their time to creating art (and later film production), and ownership was passed to Peter Birkemoe and Shane Chung,[1] who expanded operations.

[11] In 2003, Peter Birkemoe and Chris Butcher of The Beguiling first organized the Toronto Comic Arts Festival (TCAF).

[5] Rather than being like a traditional comics convention, it is patterned after European festivals such as Angoulême, and the American Small Press Expo.