Ossington Rippers were a Toronto street gang in the 1940s. Their turf was north Ossington back when the area was damned and remote and a mess of vacant lots and random run down buildings. Their clubhouse was a dirty tin-shop off an alley near the old firehall that was condemned and razed to become a subway station a decade later. Tippy Kay was their notorious leader, elected as such for being the dirtiest fighter and the sole owner of a motorcycle, stolen. Lips Franco and Twigs LaRue made headlines one summer for smoking out and robbing the bank down at the corner on Bloor. LaRue later dated and married one of the tellers. The Rippers were mainly petty thieves and vagrant pranksters. They had beer parties up by the tracks above Dupont and wandered the Christie Pits quarry smoking cigarettes and dreaming. 

Criminal Way

Savin' It Up

Sleep With Me

Rogue

Burn It Black

Keep It Comin'

Tippy's Theme

The Times

Ray Cammaert
Marshall Bureau
Michael Small

ossingtonrippers@gmail.com