His dad ran Bert's Corned Beef House - a popular biker hangout - and Oberman, who no one thought was paying much attention to what was going on around him was listening attentively and watching with an eagle eye.
"My parents were always working, just scraping to get by," the forty seven-year-old recalls, "so I used to eat lunch at Salisbury House everyday with the City workers. I wasn't lonely though - lunch was always waiting for me, the cook knew what I liked, and there was always lots on company.
Who would have known that years later Oberman would be sharing the rich past of Inkster and Main with the rest of the world in his latest book This Business With Elijah, a collection of short stories, published by Turnstone Press?
Nominated for the Journey Prize and McNally Robinson' s Book of the Year Award, This Business with Elijah captures the ethnicity, the struggle, and the determination for personal successes many North End residents had in the early sixties, and portrays it all with sensitive understanding. "It was a fascinating time, a time when neighborhoods still worked."
There were always people out on the streets when you walked to the theatre or the store. It was safe and it was friendly," remembers Oberman, adding the people and places in the book are amalgamations of many different people and haunts he knew as a child. If you re familiar at all with the area, you should be able to pick out the slightly disguised landmarks.
Oberman says he used to take delight in listening in on conversations his mother - Winnipeg's renowned psychic Dot Dobie - would have with her customers in the change rooms ("I learned how to understand people"). And although that sixth sense wasn't passed on to him, what he heard gave him an insight which he uses everyday in his writings.
"Elijah took me fifteen years to write," the high school english teacher says, "it's been a whole part of my writing development. It's taken me that long to hone my skills and strengthen my vision to bring the story out. And although it's set around a 10-year-old boy in the North End, it's really a culmination of a lot of years and experiences.
He smiles when he thinks of how things eventually come full circle. After the cover of This Business With Elijah was shot (it features a young boy gazing at two mannequins in a store front reflecting the clouds), Oberman was walking through the Exchange District with his mother. He pointed out the store, now Ragpickers Anti Fashion Emporium, where the photo had been taken and she told him a little story.
"She said 'Sheldon, did I ever tell you how your father and I met? It was right in that building at a sandwich bar'. "That's enough to make anyone believe things happen for a reason.
Oberman's credits also include published children's books such as The Always Prayer Shawl and TV Sal and the Game Show from Outer Space, a patterned relationship of writing for Fred Penner, creating over 200 questions for the junior version of "A Question of Scmples", as well as many theatre, film, television and radio experiences.
If you'd like to meet him or take in a reading, Sheldon Oberman will be performing excerpts of This Business With Elijah, at the St. Norbert Cultural Centre on June 12 at 2 p.m.